Compounds > cryptopleurine
Page last updated: 2024-12-07

cryptopleurine

Description

Cryptopleurine is an alkaloid found in the plant *Cryptocarya pleurosperma*. It has been studied for its potential anticancer properties, particularly against leukemia and solid tumors. Research has shown that cryptopleurine inhibits the growth of cancer cells by interfering with protein synthesis. Its mechanism of action involves binding to the 80S ribosome, a key component of protein synthesis machinery. This disruption leads to a decrease in protein production, ultimately causing cell death. While promising, cryptopleurine's clinical use is limited due to its toxicity. Further research is ongoing to overcome these challenges and explore its therapeutic potential. It is also being investigated for its potential antiviral activity.'

cryptopleurine: plant bark alkaloid shown to inhibit protein synthesis; RN given refers to (R)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cryptopleurine : An organic heteropentacyclic compound that is (14aR)-11,12,13,14,14a,15-hexahydro-9H-dibenzo[f,h]pyrido[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID92765
CHEMBL ID198075
CHEBI ID3932
SCHEMBL ID12780396
MeSH IDM0050170

Synonyms (28)

Synonym
NCI60_001653
9h-phenanthro[9, 11,12,13,14,14a,15-hexahydro-2,3,6-trimethoxy-, (r)-
nsc19912 ,
9h-phenanthro[9, 11,12,13,14,14a,15-hexahydro-2,3,6-trimethoxy-
cryptopleurine (i)
nsc-19912
482-22-4
cryptopleurine
(14ar)-2,3,6-trimethoxy-11,12,13,14,14a,15-hexahydro-9h-phenanthro[9,10-b]quinolizine
9h-phenanthro[9,10-b]quinolizine, 11,12,13,14,14a,15-hexahydro-2,3,6-trimethoxy-, (14ar)-
(-)-cryptopleurine
CHEMBL198075
r-cryptopleurine
chebi:3932 ,
11,12,13,14,14a,15-hexahydro-2,3,6-trimethoxy-9h-phenanthro(9,10-b)quinolizine
unii-3jzk58h75b
9h-dibenzo(f,h)pyrido(1,2-b)isoquinoline, 11,12,13,14,14a,15-hexahydro-2,3,6-trimethoxy-, (14ar)-
9h-phenanthro(9,10-b)quinolizine, 11,12,13,14,14a,15-hexahydro-2,3,6-trimethoxy-, (r)-
3jzk58h75b ,
nsc 19912
9h-dibenzo[f,h]pyrido[1,2-b]isoquinoline, 11,12,13,14,14a,15-hexahydro-2,3,6-trimethoxy-, (14ar)-
SCHEMBL12780396
(14ar)-2,3,6-trimethoxy-11,12,13,14,14a,15-hexahydro-9h-dibenzo[f,h]pyrido[1,2-b]isoquinoline
DTXSID3075414
bdbm50478890
3K8 ,
Q27106253
AKOS040748188

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" In particular, a methanesulfonamide analogue of cryptopleurine (5b) exhibited improved bioavailability and significant antitumor activity, which suggests that 5b is a promising new anticancer agent."( Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
Kim, EY; Kim, S; Kwon, Y; Lee, H; Lee, K; Lee, SK; Song, J, 2015)		0.9
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
protein synthesis inhibitorA compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
antiviral agentA substance that destroys or inhibits replication of viruses.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
organic heteropentacyclic compound
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
alkaloid antibioticAny alkaloid that has significant antibiotic properties.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Hypoxia-inducible factor 1-alphaHomo sapiens (human)IC50 (µMol)0.00870.00072.46529.2100AID378016
Endothelial PAS domain-containing protein 1Homo sapiens (human)IC50 (µMol)0.00870.00302.60028.5100AID378016
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (98)

Processvia Protein(s)Taxonomy
positive regulation of chemokine-mediated signaling pathwayHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of signaling receptor activityHypoxia-inducible factor 1-alphaHomo sapiens (human)
response to hypoxiaHypoxia-inducible factor 1-alphaHomo sapiens (human)
regulation of DNA-templated transcriptionHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIHypoxia-inducible factor 1-alphaHomo sapiens (human)
response to reactive oxygen speciesHypoxia-inducible factor 1-alphaHomo sapiens (human)
angiogenesisHypoxia-inducible factor 1-alphaHomo sapiens (human)
response to hypoxiaHypoxia-inducible factor 1-alphaHomo sapiens (human)
intracellular glucose homeostasisHypoxia-inducible factor 1-alphaHomo sapiens (human)
neural crest cell migrationHypoxia-inducible factor 1-alphaHomo sapiens (human)
epithelial to mesenchymal transitionHypoxia-inducible factor 1-alphaHomo sapiens (human)
embryonic placenta developmentHypoxia-inducible factor 1-alphaHomo sapiens (human)
B-1 B cell homeostasisHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of endothelial cell proliferationHypoxia-inducible factor 1-alphaHomo sapiens (human)
heart loopingHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of neuroblast proliferationHypoxia-inducible factor 1-alphaHomo sapiens (human)
chondrocyte differentiationHypoxia-inducible factor 1-alphaHomo sapiens (human)
glandular epithelial cell maturationHypoxia-inducible factor 1-alphaHomo sapiens (human)
connective tissue replacement involved in inflammatory response wound healingHypoxia-inducible factor 1-alphaHomo sapiens (human)
outflow tract morphogenesisHypoxia-inducible factor 1-alphaHomo sapiens (human)
cardiac ventricle morphogenesisHypoxia-inducible factor 1-alphaHomo sapiens (human)
lactate metabolic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
regulation of glycolytic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
regulation of DNA-templated transcriptionHypoxia-inducible factor 1-alphaHomo sapiens (human)
intracellular iron ion homeostasisHypoxia-inducible factor 1-alphaHomo sapiens (human)
signal transductionHypoxia-inducible factor 1-alphaHomo sapiens (human)
neuroblast proliferationHypoxia-inducible factor 1-alphaHomo sapiens (human)
lactationHypoxia-inducible factor 1-alphaHomo sapiens (human)
visual learningHypoxia-inducible factor 1-alphaHomo sapiens (human)
response to iron ionHypoxia-inducible factor 1-alphaHomo sapiens (human)
regulation of gene expressionHypoxia-inducible factor 1-alphaHomo sapiens (human)
vascular endothelial growth factor productionHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of vascular endothelial growth factor productionHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of gene expressionHypoxia-inducible factor 1-alphaHomo sapiens (human)
negative regulation of gene expressionHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of epithelial cell migrationHypoxia-inducible factor 1-alphaHomo sapiens (human)
response to muscle activityHypoxia-inducible factor 1-alphaHomo sapiens (human)
axonal transport of mitochondrionHypoxia-inducible factor 1-alphaHomo sapiens (human)
neural fold elevation formationHypoxia-inducible factor 1-alphaHomo sapiens (human)
cerebral cortex developmentHypoxia-inducible factor 1-alphaHomo sapiens (human)
bone mineralizationHypoxia-inducible factor 1-alphaHomo sapiens (human)
negative regulation of bone mineralizationHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of vascular endothelial growth factor receptor signaling pathwayHypoxia-inducible factor 1-alphaHomo sapiens (human)
TOR signalingHypoxia-inducible factor 1-alphaHomo sapiens (human)
negative regulation of TOR signalingHypoxia-inducible factor 1-alphaHomo sapiens (human)
intracellular oxygen homeostasisHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of chemokine productionHypoxia-inducible factor 1-alphaHomo sapiens (human)
regulation of transforming growth factor beta2 productionHypoxia-inducible factor 1-alphaHomo sapiens (human)
collagen metabolic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
cellular response to oxidative stressHypoxia-inducible factor 1-alphaHomo sapiens (human)
embryonic hemopoiesisHypoxia-inducible factor 1-alphaHomo sapiens (human)
insulin secretion involved in cellular response to glucose stimulusHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of insulin secretion involved in cellular response to glucose stimulusHypoxia-inducible factor 1-alphaHomo sapiens (human)
hemoglobin biosynthetic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of blood vessel endothelial cell migrationHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of erythrocyte differentiationHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of angiogenesisHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of DNA-templated transcriptionHypoxia-inducible factor 1-alphaHomo sapiens (human)
negative regulation of growthHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIHypoxia-inducible factor 1-alphaHomo sapiens (human)
muscle cell cellular homeostasisHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of hormone biosynthetic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
digestive tract morphogenesisHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of nitric-oxide synthase activityHypoxia-inducible factor 1-alphaHomo sapiens (human)
neuron apoptotic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
elastin metabolic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
intestinal epithelial cell maturationHypoxia-inducible factor 1-alphaHomo sapiens (human)
epithelial cell differentiation involved in mammary gland alveolus developmentHypoxia-inducible factor 1-alphaHomo sapiens (human)
iris morphogenesisHypoxia-inducible factor 1-alphaHomo sapiens (human)
retina vasculature development in camera-type eyeHypoxia-inducible factor 1-alphaHomo sapiens (human)
negative regulation of thymocyte apoptotic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
cellular response to interleukin-1Hypoxia-inducible factor 1-alphaHomo sapiens (human)
cellular response to hypoxiaHypoxia-inducible factor 1-alphaHomo sapiens (human)
dopaminergic neuron differentiationHypoxia-inducible factor 1-alphaHomo sapiens (human)
mesenchymal cell apoptotic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
hypoxia-inducible factor-1alpha signaling pathwayHypoxia-inducible factor 1-alphaHomo sapiens (human)
cellular response to virusHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of cytokine production involved in inflammatory responseHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of mitophagyHypoxia-inducible factor 1-alphaHomo sapiens (human)
negative regulation of miRNA transcriptionHypoxia-inducible factor 1-alphaHomo sapiens (human)
positive regulation of miRNA transcriptionHypoxia-inducible factor 1-alphaHomo sapiens (human)
negative regulation of oxidative stress-induced neuron intrinsic apoptotic signaling pathwayHypoxia-inducible factor 1-alphaHomo sapiens (human)
regulation of aerobic respirationHypoxia-inducible factor 1-alphaHomo sapiens (human)
negative regulation of reactive oxygen species metabolic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
regulation of protein neddylationHypoxia-inducible factor 1-alphaHomo sapiens (human)
negative regulation of mesenchymal cell apoptotic processHypoxia-inducible factor 1-alphaHomo sapiens (human)
regulation of transcription by RNA polymerase IIHypoxia-inducible factor 1-alphaHomo sapiens (human)
response to hypoxiaEndothelial PAS domain-containing protein 1Homo sapiens (human)
angiogenesisEndothelial PAS domain-containing protein 1Homo sapiens (human)
embryonic placenta developmentEndothelial PAS domain-containing protein 1Homo sapiens (human)
blood vessel remodelingEndothelial PAS domain-containing protein 1Homo sapiens (human)
regulation of heart rateEndothelial PAS domain-containing protein 1Homo sapiens (human)
epithelial cell maturationEndothelial PAS domain-containing protein 1Homo sapiens (human)
response to oxidative stressEndothelial PAS domain-containing protein 1Homo sapiens (human)
mitochondrion organizationEndothelial PAS domain-containing protein 1Homo sapiens (human)
signal transductionEndothelial PAS domain-containing protein 1Homo sapiens (human)
visual perceptionEndothelial PAS domain-containing protein 1Homo sapiens (human)
erythrocyte differentiationEndothelial PAS domain-containing protein 1Homo sapiens (human)
lung developmentEndothelial PAS domain-containing protein 1Homo sapiens (human)
norepinephrine metabolic processEndothelial PAS domain-containing protein 1Homo sapiens (human)
mRNA transcription by RNA polymerase IIEndothelial PAS domain-containing protein 1Homo sapiens (human)
surfactant homeostasisEndothelial PAS domain-containing protein 1Homo sapiens (human)
positive regulation of transcription by RNA polymerase IIEndothelial PAS domain-containing protein 1Homo sapiens (human)
myoblast fate commitmentEndothelial PAS domain-containing protein 1Homo sapiens (human)
multicellular organismal-level iron ion homeostasisEndothelial PAS domain-containing protein 1Homo sapiens (human)
cellular response to hypoxiaEndothelial PAS domain-containing protein 1Homo sapiens (human)
positive regulation of cold-induced thermogenesisEndothelial PAS domain-containing protein 1Homo sapiens (human)
regulation of protein neddylationEndothelial PAS domain-containing protein 1Homo sapiens (human)
regulation of transcription by RNA polymerase IIEndothelial PAS domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (23)

Processvia Protein(s)Taxonomy
DNA-binding transcription factor activity, RNA polymerase II-specificHypoxia-inducible factor 1-alphaHomo sapiens (human)
sequence-specific DNA bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
RNA polymerase II transcription regulatory region sequence-specific DNA bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificHypoxia-inducible factor 1-alphaHomo sapiens (human)
cis-regulatory region sequence-specific DNA bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
DNA-binding transcription activator activityHypoxia-inducible factor 1-alphaHomo sapiens (human)
DNA-binding transcription repressor activityHypoxia-inducible factor 1-alphaHomo sapiens (human)
transcription coactivator bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificHypoxia-inducible factor 1-alphaHomo sapiens (human)
p53 bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
DNA-binding transcription factor activityHypoxia-inducible factor 1-alphaHomo sapiens (human)
protein bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
nuclear receptor bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
enzyme bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
protein kinase bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
protein domain specific bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
ubiquitin protein ligase bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
histone deacetylase bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
protein heterodimerization activityHypoxia-inducible factor 1-alphaHomo sapiens (human)
Hsp90 protein bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
E-box bindingHypoxia-inducible factor 1-alphaHomo sapiens (human)
transcription regulator activator activityHypoxia-inducible factor 1-alphaHomo sapiens (human)
sequence-specific DNA bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificEndothelial PAS domain-containing protein 1Homo sapiens (human)
transcription coactivator bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificEndothelial PAS domain-containing protein 1Homo sapiens (human)
protein bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
protein heterodimerization activityEndothelial PAS domain-containing protein 1Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
RNA polymerase II transcription regulatory region sequence-specific DNA bindingEndothelial PAS domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
nucleusHypoxia-inducible factor 1-alphaHomo sapiens (human)
nucleoplasmHypoxia-inducible factor 1-alphaHomo sapiens (human)
cytoplasmHypoxia-inducible factor 1-alphaHomo sapiens (human)
cytosolHypoxia-inducible factor 1-alphaHomo sapiens (human)
nuclear bodyHypoxia-inducible factor 1-alphaHomo sapiens (human)
nuclear speckHypoxia-inducible factor 1-alphaHomo sapiens (human)
motile ciliumHypoxia-inducible factor 1-alphaHomo sapiens (human)
axon cytoplasmHypoxia-inducible factor 1-alphaHomo sapiens (human)
chromatinHypoxia-inducible factor 1-alphaHomo sapiens (human)
euchromatinHypoxia-inducible factor 1-alphaHomo sapiens (human)
protein-containing complexHypoxia-inducible factor 1-alphaHomo sapiens (human)
RNA polymerase II transcription regulator complexHypoxia-inducible factor 1-alphaHomo sapiens (human)
nucleoplasmEndothelial PAS domain-containing protein 1Homo sapiens (human)
cytosolEndothelial PAS domain-containing protein 1Homo sapiens (human)
nuclear speckEndothelial PAS domain-containing protein 1Homo sapiens (human)
chromatinEndothelial PAS domain-containing protein 1Homo sapiens (human)
transcription regulator complexEndothelial PAS domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (83)

Assay IDTitleYearJournalArticle
AID1251581Solubility of the compound in 1:1 mixture of phosphate buffer and EtOH2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1388909Allosteric regulation of recombinant HSC70 (unknown origin) ATPase activity assessed as increase in ADP production at 10 uM after 10 mins in presence of HCV wild type poly U/UC RNA by HPLC analysis2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID1176194Antiproliferative activity against human NAMALWA cells after 72 hrs by ATPlite assay2015Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2
Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs.
AID698589Downregulation of HSP90 protein expression in human A549 cells at 3.6 to 100 nM after 48 hrs by Western blot analysis2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID378021Inhibition of hypoxia-induced HIF1alpha protein accumulation in human AGS cells after 12 hrs by Western blot2006Journal of natural products, Jul, Volume: 69, Issue:7
Phenanthroquinolizidine alkaloids from the roots of Boehmeria pannosa potently inhibit hypoxia-inducible factor-1 in AGS human gastric cancer cells.
AID698590Downregulation of beta-casein protein expression in human A549 cells at 3.6 to 100 nM after 48 hrs by Western blot analysis2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID1251602Cell cycle arrest in human Caki1 cells assessed as accumulation at S phase at 1000 pM after 24 hrs by flow cytometry (Rvb = 13.4%)2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID258659Cytotoxicity against HEK293 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID1176191Antiproliferative activity against human A549 cells after 72 hrs by ATPlite assay2015Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2
Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs.
AID378016Inhibition of hypoxia-induced HIF1 activation in human AGS cells after 16 hrs by pGL3-HRE-luciferase reporter gene assay2006Journal of natural products, Jul, Volume: 69, Issue:7
Phenanthroquinolizidine alkaloids from the roots of Boehmeria pannosa potently inhibit hypoxia-inducible factor-1 in AGS human gastric cancer cells.
AID698605Cytotoxicity against human A549 cells after 2 hrs by methylene blue staining-based spectrophotometric analysis2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID1251588Oral bioavailability in ICR mouse at 10 mg/kg2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1251584Volume of distribution at steady state in ICR mouse at 1 mg/kg, iv2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1388904Antiviral activity against HCV genotype 1b con1 infected in human Huh-luc/neo-ET cells assessed as inhibition of viral replication after 72 hrs2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID698604Cytotoxicity against human DU145 cells after 2 hrs by methylene blue staining-based spectrophotometric analysis2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID258655Cytotoxicity against human colon carcinoma, HCT15 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID698602Cytotoxicity against human KB cells after 2 hrs by methylene blue staining-based spectrophotometric analysis2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID610918Anticancer activity against human KB cells after 72 hrs by sulforhodamine B assay2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Antitumor agents 288: design, synthesis, SAR, and biological studies of novel heteroatom-incorporated antofine and cryptopleurine analogues as potent and selective antitumor agents.
AID1251587Elimination half-life in ICR mouse plasma at 10 mg/kg, po2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1388914Induction of HSC70 chaperone activity in human Huh-luc/neo-ET cells assessed as reduction in HCV RNA NS3 protein expression at 3 nM after 24 hrs2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID258665Cytotoxicity against human breast carcinoma, MCF7 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID258666Cytotoxicity against murine cytotoxic T cells, CTLL22006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID258663Cytotoxicity against human uterine sarcoma, MES-SA cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID698597Cytotoxicity against human PC9IR cells assessed as cell viability after 48 hrs by SRB assay2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID698598Cytotoxicity against human A549 cells assessed as cell viability after 48 hrs by SRB assay2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID648632Antiproliferative activity against human A549 cells after 72 hrs by MTT assay2012European journal of medicinal chemistry, May, Volume: 51Synthesis and SAR studies of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potent anti-tumor agents.
AID1251601Cell cycle arrest in human Caki1 cells assessed as accumulation at G0/G1 phase at 1000 pM after 24 hrs by flow cytometry (Rvb = 56.9%)2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1176192Antiproliferative activity against human A375 cells after 72 hrs by ATPlite assay2015Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2
Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs.
AID1251628Cytotoxicity against human PC3 cells assessed as growth inhibition after 72 hrs by SRB assay2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID378019Inhibition of hypoxia-induced HIF1 activation in human AGS cells at 100 nM after 16 hrs by pGL3-HRE-luciferase reporter gene assay2006Journal of natural products, Jul, Volume: 69, Issue:7
Phenanthroquinolizidine alkaloids from the roots of Boehmeria pannosa potently inhibit hypoxia-inducible factor-1 in AGS human gastric cancer cells.
AID258649Cytotoxicity against human breast carcinoma, BT20 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID1176193Antiproliferative activity against human HCT116 cells after 72 hrs by ATPlite assay2015Bioorganic & medicinal chemistry letters, Jan-15, Volume: 25, Issue:2
Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs.
AID378017Inhibition of hypoxia-induced HIF1beta protein accumulation in human AGS cells after 12 hrs by Western blot2006Journal of natural products, Jul, Volume: 69, Issue:7
Phenanthroquinolizidine alkaloids from the roots of Boehmeria pannosa potently inhibit hypoxia-inducible factor-1 in AGS human gastric cancer cells.
AID1388916Induction of HSC70 chaperone activity in human Huh-luc/neo-ET cells co-transfected with FLAG-tagged CHIP assessed as reduction in HCV RNA NS3 protein expression at 3 nM after 24 hrs2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID1251623Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs by SRB assay2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID610917Anticancer activity against human DU145 cells after 72 hrs by sulforhodamine B assay2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Antitumor agents 288: design, synthesis, SAR, and biological studies of novel heteroatom-incorporated antofine and cryptopleurine analogues as potent and selective antitumor agents.
AID1388912Induction of HSC70 (unknown origin) chaperone activity assessed as reactivation of guanidine-denatured luciferase by luciferase reporter gene assay2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID1251592Cell cycle arrest in human Caki1 cells assessed as accumulation at sub-G1 phase at 1000 pM after 24 hrs by flow cytometry (Rvb = 0.8%)2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1388919Induction of HSC70 chaperone activity in human Huh-luc/neo-ET cells co-transfected with FLAG-tagged CHIP assessed as reduction in HCV RNA NS5A protein expression at 3 nM after 24 hrs2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID1388918Induction of HSC70 chaperone activity in human Huh-luc/neo-ET cells assessed as reduction in HCV RNA NS5A protein expression at 3 nM after 24 hrs2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID698600Cytotoxicity against human CL1-5 cells assessed as cell viability after 48 hrs by SRB assay2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID698561Cytotoxicity against human HCT8 cells after 2 hrs by methylene blue staining-based spectrophotometric analysis2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID258660Cytotoxicity against human fibroblast, BUD8 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID1388908Cytotoxicity against human HepG2(2.2.15) cells assessed as cell growth inhibition2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID1388923Effect on HSC70 expression in human HepG2(2.2.15) cells at 3 nM measured up to 72 hrs by Western blot analysis2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID1251585AUC (0 to infinity) in ICR mouse at 1 mg/kg, iv2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID258651Cytotoxicity against human osteosarcoma, KHOS-NP cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID1251629Cytotoxicity against human Caki1 cells assessed as growth inhibition after 72 hrs by SRB assay2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1251627Cytotoxicity against human SKHEP1 cells assessed as growth inhibition after 72 hrs by SRB assay2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1251624Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 hrs by SRB assay2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1251589AUC (0 to infinity) in ICR mouse at 10 mg/kg, po2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1388905Cytotoxicity against human Huh-luc/neo-ET cells assessed as cell growth inhibition2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID258657Cytotoxicity against human ovarian teratocarcinoma, PA1 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID1251583Elimination half-life in ICR mouse plasma at 1 mg/kg, iv2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1251625Cytotoxicity against human SNU638 cells assessed as growth inhibition after 72 hrs by SRB assay2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID258664Cytotoxicity against human uterine sarcoma, MES-SA-Dx5 cells derived from MES-SA2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID258662Cytotoxicity against human Burkitt lymphoma, DAUDI cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID1388913Induction of HSC70 (unknown origin) chaperone activity assessed as reactivation of guanidine-denatured luciferase at 10 uM in presence of human recombinant CHIP by luciferase reporter gene assay2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID258654Cytotoxicity against human lung carcinoma, A549 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID378018Inhibition of hypoxia-induced VEGF expression in human AGS cells after 16 hrs by RT-PCR analysis2006Journal of natural products, Jul, Volume: 69, Issue:7
Phenanthroquinolizidine alkaloids from the roots of Boehmeria pannosa potently inhibit hypoxia-inducible factor-1 in AGS human gastric cancer cells.
AID258653Cytotoxicity against human melanoma, A375 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID610916Anticancer activity against human A549 cells after 72 hrs by sulforhodamine B assay2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Antitumor agents 288: design, synthesis, SAR, and biological studies of novel heteroatom-incorporated antofine and cryptopleurine analogues as potent and selective antitumor agents.
AID1388907Antiviral activity against HBV infected in human HepG2(2.2.15) cells assessed as inhibition of viral DNA level after 6 days by Southern blot analysis2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID1251626Cytotoxicity against human MDA-MB-231 cells assessed as growth inhibition after 72 hrs by SRB assay2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID258648Cytotoxicity against human erythroleukemia TF1 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID1388921Effect on FLAF-tagged CHIP expression in human Huh-luc/neo-ET cells at 3 nM after 24 hrs2018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID258661Cytotoxicity against human Burkitt lymphoma, RAMOS cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID1251586Cmax in ICR mouse plasma at 10 mg/kg, po2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID1388906Therapeutic index, ratio of IC50 for human Huh-luc/neo-ET cells to EC50 for HCV genotype 1b con12018Bioorganic & medicinal chemistry, 02-01, Volume: 26, Issue:3
Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.
AID1251673Solubility of the compound in phosphate buffer at pH 7.42015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID698588Downregulation of cyclin D protein expression in human A549 cells at 3.6 to 100 nM after 48 hrs by Western blot analysis2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID1251603Cell cycle arrest in human Caki1 cells assessed as accumulation at G2/M phase at 1000 pM after 24 hrs by flow cytometry (Rvb = 28.9%)2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID610948Toxicity against HUVEC2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Antitumor agents 288: design, synthesis, SAR, and biological studies of novel heteroatom-incorporated antofine and cryptopleurine analogues as potent and selective antitumor agents.
AID258652Cytotoxicity against human epidermoid carcinoma, A431 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID648628Antiproliferative activity against human HL60 cells after 72 hrs by SRB assay2012European journal of medicinal chemistry, May, Volume: 51Synthesis and SAR studies of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potent anti-tumor agents.
AID258656Cytotoxicity against human bladder carcinoma, HT1376 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID698595Cytotoxicity against human MRC5 cells assessed as cell viability after 48 hrs by SRB assay2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID258650Cytotoxicity against rat prostate carcinoma, MatLyLu cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
AID610919Anticancer activity against human HCT8 cells after 72 hrs by sulforhodamine B assay2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Antitumor agents 288: design, synthesis, SAR, and biological studies of novel heteroatom-incorporated antofine and cryptopleurine analogues as potent and selective antitumor agents.
AID698599Cytotoxicity against human CL1-0 cells assessed as cell viability after 48 hrs by SRB assay2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID698596Cytotoxicity against human PC9 cells assessed as cell viability after 48 hrs by SRB assay2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.
AID1251582Clearance in ICR mouse plasma at 1 mg/kg, iv2015Journal of medicinal chemistry, Oct-08, Volume: 58, Issue:19
Design, Synthesis, and Biological Activity of Sulfonamide Analogues of Antofine and Cryptopleurine as Potent and Orally Active Antitumor Agents.
AID258658Cytotoxicity against human hepatoma, HEPG2 cells2006Bioorganic & medicinal chemistry letters, Jan-01, Volume: 16, Issue:1
C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-199012 (36.36)18.7374
1990's2 (6.06)18.2507
2000's5 (15.15)29.6817
2010's14 (42.42)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.66

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.66 (24.57)
Research Supply Index3.53 (2.92)
Research Growth Index4.89 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.66)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other33 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
1-butanol
1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.		2.0210alkyl alcohol;
primary alcohol;
short-chain primary fatty alcohol		human metabolite;
mouse metabolite;
protic solvent
carbamates
[no description available]		1.9610amino-acid anion
phenanthrene
phenanthrene : A polycyclic aromatic hydrocarbon composed of three fused benzene rings which takes its name from the two terms 'phenyl' and 'anthracene.'		2.110ortho-fused polycyclic arene;
ortho-fused tricyclic hydrocarbon;
phenanthrenes		environmental contaminant;
mouse metabolite
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		1.9510amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
cycloheximide
Cycloheximide: Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.. cycloheximide : A dicarboximide that is 4-(2-hydroxyethyl)piperidine-2,6-dione in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 3,5-dimethyl-2-oxocyclohexyl group. It is an antibiotic produced by the bacterium Streptomyces griseus.		2.6430antibiotic fungicide;
cyclic ketone;
dicarboximide;
piperidine antibiotic;
piperidones;
secondary alcohol		anticoronaviral agent;
bacterial metabolite;
ferroptosis inhibitor;
neuroprotective agent;
protein synthesis inhibitor
emetine
Emetine: The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.. emetine : A pyridoisoquinoline comprising emetam having methoxy substituents at the 6'-, 7'-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.		3.2160isoquinoline alkaloid;
pyridoisoquinoline		antiamoebic agent;
anticoronaviral agent;
antiinfective agent;
antimalarial;
antineoplastic agent;
antiprotozoal drug;
antiviral agent;
autophagy inhibitor;
emetic;
expectorant;
plant metabolite;
protein synthesis inhibitor
carbendazim
carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.		1.9610benzimidazole fungicide;
benzimidazoles;
benzimidazolylcarbamate fungicide;
carbamate ester		antifungal agrochemical;
antinematodal drug;
metabolite;
microtubule-destabilising agent
1,7-phenanthroline
[no description available]		3.84110phenanthroline
tubulosine
tubulosine: indole derivative of main alkaloids of ipecac; RN given refers to cpd with unspecified isomeric designation; structure. tubulosine : A member of the class of beta-carbolines that is tubulosan bearing methoxy groups at positions 10 and 11 and a hydroxy group at the 8' position.		7.3620beta-carbolines;
isoquinoline alkaloid;
isoquinolines;
phenols;
secondary amino compound;
tertiary amino compound
methanesulfonamide
[no description available]		2.1110
tylophorine
tylophorine: phenanthroindolizidine alkaloid		2.9840organic heteropentacyclic compound;
organonitrogen heterocyclic compound
proline
Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.		7.0510amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
anisomycin
Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.		1.9510monohydroxypyrrolidine;
organonitrogen heterocyclic antibiotic		anticoronaviral agent;
antimicrobial agent;
antineoplastic agent;
antiparasitic agent;
bacterial metabolite;
DNA synthesis inhibitor;
protein synthesis inhibitor
dcb 3503
[no description available]		2.5220
cephaelin
cephaelin: do not confuse with cephalin of brain; after emetine this is the most important alkaloid of ipecac; protein synthesis inhibitor. cephaeline : A pyridoisoquinoline comprising emetam having a hydroxy group at the 6'-position and methoxy substituents at the 7'-, 10- and 11-positions.		1.9510pyridoisoquinoline
stilbenes
Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.		2.0310stilbene
antofine
antofine: structure in first source. (-)-antofine : An organic heteropentacyclic compound that is (13aR)-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline substituted at positions 2, 3 and 6 by methoxy groups. It is an alkaloid produced by relatives of the milkweed family and exhibits antiviral, anti-inflammatory, antiadipogenic and antitumorigenic activities.		3.85110alkaloid antibiotic;
alkaloid;
aromatic ether;
organic heteropentacyclic compound		angiogenesis inhibitor;
anti-inflammatory agent;
antimicrobial agent;
antineoplastic agent;
antiviral agent;
phytotoxin;
plant metabolite
tert-butanesulfinamide
tert-butanesulfinamide: structure in first source		7.110
pactamycin
Pactamycin: Antibiotic produced by Streptomyces pactum used as an antineoplastic agent. It is also used as a tool in biochemistry because it inhibits certain steps in protein synthesis.		1.9510
fosbretabulin
fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source		2.0310
manassantin b
manassantin B: isolated from the roots of Saururus chinensis; structure in first source. manassantin B : A lignan isolated from Saururus cernuus and Saururus chinensis and has been shown to exhibit antineoplastic activity.		2.0310benzodioxoles;
dimethoxybenzene;
lignan;
oxolanes;
secondary alcohol		antineoplastic agent;
metabolite
piperidines
Piperidines: A family of hexahydropyridines.		2.0210
trichodermin
Trichodermin: Antifungal metabolite from several fungi, mainly Trichoderma viride; inhibits protein synthesis by binding to ribosomes; proposed as antifungal and antineoplastic; used as tool in cellular biochemistry.. trichodermin : A tetracyclic spiroepoxide which acts as an antifungal and protein synthesis inhibitor.		1.9510
sparsomycin
Sparsomycin: An antitumor antibiotic produced by Streptomyces sparsogenes. It inhibits protein synthesis in 70S and 80S ribosomal systems.		1.9510
guanosine triphosphate
Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.		1.9510guanosine 5'-phosphate;
purine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
concanavalin a
Concanavalin A: A MANNOSE/GLUCOSE binding lectin isolated from the jack bean (Canavalia ensiformis). It is a potent mitogen used to stimulate cell proliferation in lymphocytes, primarily T-lymphocyte, cultures.		1.9610
phenanthrenes
Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.		3.690
ConditionIndicatedRelationship StrengthStudiesTrials
Anoxemia
[description not available]		02.4620
Cancer of Stomach
[description not available]		02.0310
Hypoxia
Sub-optimal OXYGEN levels in the ambient air of living organisms.		02.4620
Stomach Neoplasms
Tumors or cancer of the STOMACH.		02.0310
Adenocarcinoma, Basal Cell
[description not available]		02.0710
Carcinoma, Non-Small Cell Lung
[description not available]		02.0710
Cancer of Lung
[description not available]		02.0710
Adenocarcinoma
A malignant epithelial tumor with a glandular organization.		02.0710
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		02.0710
Lung Neoplasms
Tumors or cancer of the LUNG.		02.0710
Benign Neoplasms
[description not available]		02.520
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.520
Colorectal Cancer
[description not available]		02.1110
Colorectal Neoplasms
Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.		02.1110
Innate Inflammatory Response
[description not available]		02.0710
Angiogenesis, Pathologic
[description not available]		02.0710
Invasiveness, Neoplasm
[description not available]		02.0710
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0710
Abnormalities, Autosome
[description not available]		02.3620
Chromosomal Translocation
[description not available]		01.9510
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