Page last updated: 2024-12-08

gl 331

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Description

GL 331: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID148091
CHEMBL ID283631
SCHEMBL ID5953587
MeSH IDM0333981

Synonyms (24)

Synonym
nsc-628679
127882-73-9
furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[(4-nitrophenyl)amino]-, (5r,5ar,8as,9s)-
(5s,5as,8ar,9r)-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5h-isobenzofuro[5,6-f][1,3]benzodioxol-8-one
CHEMBL283631 ,
(5s,5as,8ar,9r)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroanilino)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-nitrophenyl)amino)-furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, (5r-(5alpha,5abeta,8aalpha,9beta))-
(5r-(5alpha,5abeta,8aalpha,9beta))-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-nitrophenyl)amino)furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one
unii-0i81858vsz
furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-nitrophenyl)amino)-, (5r,5ar,8as,9s)-
gl 331
gl331
gl-331
0i81858vsz ,
nsc 628672
SCHEMBL5953587
furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-nitrophenyl)amino)-, (5r-(5.alpha.,5a.beta.,8a.alpha.,9.beta.))-
w-68
DTXSID40155689
Q27236812
(5r,5ar,8as,9s)-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-((4-nitrophenyl)amino)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5ah)-one
bdbm50524833
GLXC-26880
AKOS040748431

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"A phase II and pharmacokinetic study was designed to assess the efficacy and toxicity profile of an epidophyllotoxin analogue, GL331, in previously treated Chinese gastric cancer patients, with concurrent pharmacokinetic evaluation of the drug's metabolism."( Phase II and pharmacokinetic study of GL331 in previously treated Chinese gastric cancer patients.
Chang, JY; Chao, Y; Chen, JD; Chen, LT; Lan, C; Li, AF; Lin, WC; Liu, JM; Liu, TS; Shiah, HS; Whang-Peng, J; Wu, CW; Wu, HW, 2002
)
0.31

Compound-Compound Interactions

ExcerptReferenceRelevance
" In addition to evaluation of GL331's single agent activity, the use of GL331 in combination with other established therapeutic agents was also evaluated."( In vitro evaluation of GL331's cancer cell killing and apoptosis-inducing activity in combination with other chemotherapeutic agents.
Chen, LT; Huang, TS; Lee, CC; Shu, CH; Whang-Peng, J, 2000
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Hypoxia-inducible factor 1-alphaHomo sapiens (human)IC50 (µMol)0.00100.00072.46529.2100AID1597989
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA topoisomerase 2-alphaHomo sapiens (human)IC100 (µMol)10.000010.000010.000010.0000AID57193
DNA topoisomerase 2-alphaHomo sapiens (human)ID5010.00005.00007.500010.0000AID335667; AID53299; AID53300; AID57202; AID57205
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)ID5010.000010.000010.000010.0000AID53300
DNA topoisomerase 2-betaHomo sapiens (human)IC100 (µMol)10.000010.000010.000010.0000AID57193
DNA topoisomerase 2-betaHomo sapiens (human)ID5010.00005.00007.500010.0000AID53299; AID53300; AID57202; AID57205
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (107)

Processvia Protein(s)Taxonomy
hematopoietic progenitor cell differentiationDNA topoisomerase 2-alphaHomo sapiens (human)
DNA topological changeDNA topoisomerase 2-alphaHomo sapiens (human)
DNA ligationDNA topoisomerase 2-alphaHomo sapiens (human)
DNA damage responseDNA topoisomerase 2-alphaHomo sapiens (human)
chromosome segregationDNA topoisomerase 2-alphaHomo sapiens (human)
female meiotic nuclear divisionDNA topoisomerase 2-alphaHomo sapiens (human)
apoptotic chromosome condensationDNA topoisomerase 2-alphaHomo sapiens (human)
embryonic cleavageDNA topoisomerase 2-alphaHomo sapiens (human)
regulation of circadian rhythmDNA topoisomerase 2-alphaHomo sapiens (human)
positive regulation of apoptotic processDNA topoisomerase 2-alphaHomo sapiens (human)
positive regulation of single stranded viral RNA replication via double stranded DNA intermediateDNA topoisomerase 2-alphaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIDNA topoisomerase 2-alphaHomo sapiens (human)
rhythmic processDNA topoisomerase 2-alphaHomo sapiens (human)
negative regulation of DNA duplex unwindingDNA topoisomerase 2-alphaHomo sapiens (human)
resolution of meiotic recombination intermediatesDNA topoisomerase 2-alphaHomo sapiens (human)
sister chromatid segregationDNA topoisomerase 2-alphaHomo sapiens (human)
neuron migrationDNA topoisomerase 2-betaHomo sapiens (human)
DNA topological changeDNA topoisomerase 2-betaHomo sapiens (human)
axonogenesisDNA topoisomerase 2-betaHomo sapiens (human)
B cell differentiationDNA topoisomerase 2-betaHomo sapiens (human)
forebrain developmentDNA topoisomerase 2-betaHomo sapiens (human)
positive regulation of single stranded viral RNA replication via double stranded DNA intermediateDNA topoisomerase 2-betaHomo sapiens (human)
cellular response to hydrogen peroxideDNA topoisomerase 2-betaHomo sapiens (human)
cellular response to ATPDNA topoisomerase 2-betaHomo sapiens (human)
cellular senescenceDNA topoisomerase 2-betaHomo sapiens (human)
positive regulation of double-strand break repair via nonhomologous end joiningDNA topoisomerase 2-betaHomo sapiens (human)
sister chromatid segregationDNA topoisomerase 2-betaHomo sapiens (human)
resolution of meiotic recombination intermediatesDNA topoisomerase 2-betaHomo sapiens (human)
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (36)

Processvia Protein(s)Taxonomy
magnesium ion bindingDNA topoisomerase 2-alphaHomo sapiens (human)
DNA bindingDNA topoisomerase 2-alphaHomo sapiens (human)
chromatin bindingDNA topoisomerase 2-alphaHomo sapiens (human)
RNA bindingDNA topoisomerase 2-alphaHomo sapiens (human)
DNA topoisomerase type II (double strand cut, ATP-hydrolyzing) activityDNA topoisomerase 2-alphaHomo sapiens (human)
protein kinase C bindingDNA topoisomerase 2-alphaHomo sapiens (human)
protein bindingDNA topoisomerase 2-alphaHomo sapiens (human)
ATP bindingDNA topoisomerase 2-alphaHomo sapiens (human)
ATP-dependent activity, acting on DNADNA topoisomerase 2-alphaHomo sapiens (human)
DNA binding, bendingDNA topoisomerase 2-alphaHomo sapiens (human)
protein homodimerization activityDNA topoisomerase 2-alphaHomo sapiens (human)
ubiquitin bindingDNA topoisomerase 2-alphaHomo sapiens (human)
protein heterodimerization activityDNA topoisomerase 2-alphaHomo sapiens (human)
DNA bindingDNA topoisomerase 2-betaHomo sapiens (human)
chromatin bindingDNA topoisomerase 2-betaHomo sapiens (human)
DNA topoisomerase type II (double strand cut, ATP-hydrolyzing) activityDNA topoisomerase 2-betaHomo sapiens (human)
protein bindingDNA topoisomerase 2-betaHomo sapiens (human)
ATP bindingDNA topoisomerase 2-betaHomo sapiens (human)
ribonucleoprotein complex bindingDNA topoisomerase 2-betaHomo sapiens (human)
metal ion bindingDNA topoisomerase 2-betaHomo sapiens (human)
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (21)

Processvia Protein(s)Taxonomy
nucleolusDNA topoisomerase 2-alphaHomo sapiens (human)
nuclear chromosomeDNA topoisomerase 2-alphaHomo sapiens (human)
centrioleDNA topoisomerase 2-alphaHomo sapiens (human)
chromosome, centromeric regionDNA topoisomerase 2-alphaHomo sapiens (human)
condensed chromosomeDNA topoisomerase 2-alphaHomo sapiens (human)
male germ cell nucleusDNA topoisomerase 2-alphaHomo sapiens (human)
nucleusDNA topoisomerase 2-alphaHomo sapiens (human)
nucleoplasmDNA topoisomerase 2-alphaHomo sapiens (human)
nucleolusDNA topoisomerase 2-alphaHomo sapiens (human)
cytoplasmDNA topoisomerase 2-alphaHomo sapiens (human)
DNA topoisomerase type II (double strand cut, ATP-hydrolyzing) complexDNA topoisomerase 2-alphaHomo sapiens (human)
protein-containing complexDNA topoisomerase 2-alphaHomo sapiens (human)
ribonucleoprotein complexDNA topoisomerase 2-alphaHomo sapiens (human)
nucleusDNA topoisomerase 2-alphaHomo sapiens (human)
nucleolusDNA topoisomerase 2-betaHomo sapiens (human)
heterochromatinDNA topoisomerase 2-betaHomo sapiens (human)
nucleusDNA topoisomerase 2-betaHomo sapiens (human)
nucleoplasmDNA topoisomerase 2-betaHomo sapiens (human)
nucleolusDNA topoisomerase 2-betaHomo sapiens (human)
cytosolDNA topoisomerase 2-betaHomo sapiens (human)
ribonucleoprotein complexDNA topoisomerase 2-betaHomo sapiens (human)
nucleusDNA topoisomerase 2-betaHomo sapiens (human)
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (68)

Assay IDTitleYearJournalArticle
AID95665The compound was tested for tumor cell growth inhibitory activity against human nasopharynx carcinoma(KB) cell line.1999Journal of medicinal chemistry, Jul-01, Volume: 42, Issue:13
Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4'-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles.
AID202816The compound was tested for tumor cell growth inhibitory activity against human melanoma (SKMEL-2) cell line.1999Journal of medicinal chemistry, Jul-01, Volume: 42, Issue:13
Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4'-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles.
AID103730The compound was tested for tumor cell growth inhibitory activity against human breast cancer (MCF-7) cell line.1999Journal of medicinal chemistry, Jul-01, Volume: 42, Issue:13
Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4'-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles.
AID96033The compound was tested for cytotoxic activity against KB cell line by clonogenic cell survival assay.1999Journal of medicinal chemistry, Jul-01, Volume: 42, Issue:13
Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4'-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles.
AID80116Inhibitory activity against human cytomegalovirus (HCMV)2001Journal of medicinal chemistry, Apr-26, Volume: 44, Issue:9
Antitumor agents. 207. Design, synthesis, and biological testing of 4beta-anilino-2-fluoro-4'-demethylpodophyllotoxin analogues as cytotoxic and antiviral agents.
AID94331Growth inhibitory activity (antiproliferative) against KB/7d cell lines1996Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7
Antitumor agents. 164. Podophenazine, 2'',3''-dichloropodophenazine, benzopodophenazine, and their 4 beta-p-nitroaniline derivatives as novel DNA topoisomerase II inhibitors.
AID1760332Antiproliferative activity against human A549 cells incubated for 72 hrs by MTT assay2020European journal of medicinal chemistry, Dec-15, Volume: 208Recent advances of podophyllotoxin/epipodophyllotoxin hybrids in anticancer activity, mode of action, and structure-activity relationship: An update (2010-2020).
AID84364Effective dose of compound against replication of HOS cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID1760331Antiproliferative activity against human MCF7 cells incubated for 72 hrs by MTT assay2020European journal of medicinal chemistry, Dec-15, Volume: 208Recent advances of podophyllotoxin/epipodophyllotoxin hybrids in anticancer activity, mode of action, and structure-activity relationship: An update (2010-2020).
AID246896Dose required for reduction in human nasopharyngeal KB-7d cancer cells after 3 days incubation2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Antitumor agents. 234. Design, synthesis, and biological evaluation of novel 4beta-[(4' '-benzamido)-amino]-4'-o-demethyl-epipodophyllotoxin derivatives.
AID201790Effective dose of compound against replication of SK-MEL-2 cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID78815Effective dose of compound against replication of HCT-8 cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID53300Inhibition of human DNA Topoisomerase II1992Journal of medicinal chemistry, Mar-06, Volume: 35, Issue:5
Antitumor agents. 124. New 4 beta-substituted aniline derivatives of 6,7-O,O-demethylene-4'-O-demethylpodophyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II.
AID52062Compound was tested for the % complex formation of cellular protein -DNA complex at a concentration of 10 uM1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Antitumor agents. 120. New 4-substituted benzylamine and benzyl ether derivatives of 4'-O-demethylepipodophyllotoxin as potent inhibitors of human DNA topoisomerase II.
AID211317Stimulation of in vitro Topoisomerase II-Linked DNA Complex Formation and Interference with Etoposide-Induced Cleavage at concentration 100 uM; Not determined1996Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7
Antitumor agents. 164. Podophenazine, 2'',3''-dichloropodophenazine, benzopodophenazine, and their 4 beta-p-nitroaniline derivatives as novel DNA topoisomerase II inhibitors.
AID2963Effective dose of compound against replication of 1A9 cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID8466Effective dose of compound against replication of A549 cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID667142Cytotoxicity against human DU145 cells by SRB assay2012Bioorganic & medicinal chemistry letters, Jul-01, Volume: 22, Issue:13
Synthesis and evaluation of novel podophyllotoxin analogs.
AID96387Compound was tested for the concentration to afford 50% reduction in KB cell number after a 3-day incubation1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Antitumor agents. 120. New 4-substituted benzylamine and benzyl ether derivatives of 4'-O-demethylepipodophyllotoxin as potent inhibitors of human DNA topoisomerase II.
AID156027Effective dose of compound against replication of PC-3 cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID492486Cytotoxicity against human KB-7d cells after 72 hrs by MTT assay2010Journal of natural products, Mar-26, Volume: 73, Issue:3
Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.
AID57061Percentage of intracellular covalent DNA-topoisomerase II complexes formed2002Journal of medicinal chemistry, May-23, Volume: 45, Issue:11
Antitumor agents. 213. Modeling of epipodophyllotoxin derivatives using variable selection k nearest neighbor QSAR method.
AID335669Inhibition of strand rejoining activity of human DNA topoisomerase 2 assessed as protein-DNA complex formation at 10 uM by cell-based assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 130, Novel 4 beta-arylamino derivatives of 3',4'-didemethoxy-3',4'-dioxo-4-deoxypodophyllotoxin as potent inhibitors of human DNA topoisomerase II.
AID95840Growth inhibitory activity (antiproliferative) against KB cell lines1996Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7
Antitumor agents. 164. Podophenazine, 2'',3''-dichloropodophenazine, benzopodophenazine, and their 4 beta-p-nitroaniline derivatives as novel DNA topoisomerase II inhibitors.
AID42742GI values against CAKI-1 cells(renal carcinoma)2001Journal of medicinal chemistry, Apr-26, Volume: 44, Issue:9
Antitumor agents. 207. Design, synthesis, and biological testing of 4beta-anilino-2-fluoro-4'-demethylpodophyllotoxin analogues as cytotoxic and antiviral agents.
AID96389Concentration for 50% reduction in cell number after 3-day incubation1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Antitumor agents. 113. New 4 beta-arylamino derivatives of 4'-O-demethylepipodophyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II.
AID93836GI values against KB cells (nasopharyngeal carcinoma)2001Journal of medicinal chemistry, Apr-26, Volume: 44, Issue:9
Antitumor agents. 207. Design, synthesis, and biological testing of 4beta-anilino-2-fluoro-4'-demethylpodophyllotoxin analogues as cytotoxic and antiviral agents.
AID57193The compound was tested for inhibitory activity against human DNA topoisomerase-2.1999Journal of medicinal chemistry, Jul-01, Volume: 42, Issue:13
Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4'-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles.
AID52061Effect on cellular protein DNA complex formation(%) at 10 uM in comparison with etoposide1992Journal of medicinal chemistry, Mar-06, Volume: 35, Issue:5
Antitumor agents. 124. New 4 beta-substituted aniline derivatives of 6,7-O,O-demethylene-4'-O-demethylpodophyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II.
AID103709Effective dose of compound against replication of MCF-7 cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID253085Ratio of ED50 for KB-7d cells to that of KB cells2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Antitumor agents. 234. Design, synthesis, and biological evaluation of novel 4beta-[(4' '-benzamido)-amino]-4'-o-demethyl-epipodophyllotoxin derivatives.
AID667143Cytotoxicity against human KB cells by SRB assay2012Bioorganic & medicinal chemistry letters, Jul-01, Volume: 22, Issue:13
Synthesis and evaluation of novel podophyllotoxin analogs.
AID42573The compound was tested for tumor cell growth inhibitory activity against human renal cancer(CAKI-1) cell line1999Journal of medicinal chemistry, Jul-01, Volume: 42, Issue:13
Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4'-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles.
AID667144Cytotoxicity against human KBVIN cells by SRB assay2012Bioorganic & medicinal chemistry letters, Jul-01, Volume: 22, Issue:13
Synthesis and evaluation of novel podophyllotoxin analogs.
AID94007Compound was evaluated for cytotoxicity against KB-7d cells at 10 uM concentration2004Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11
Antitumor agents. Part 230: C4'-esters of GL-331 as cytotoxic agents and DNA topoisomerase II inhibitors.
AID1760330Antiproliferative activity against human PC3 cells incubated for 72 hrs by MTT assay2020European journal of medicinal chemistry, Dec-15, Volume: 208Recent advances of podophyllotoxin/epipodophyllotoxin hybrids in anticancer activity, mode of action, and structure-activity relationship: An update (2010-2020).
AID94009Effective dose required for inhibition of KB-7d cell replication after 3 days of continuous treatment2004Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11
Antitumor agents. Part 230: C4'-esters of GL-331 as cytotoxic agents and DNA topoisomerase II inhibitors.
AID57202Compound was tested for the inhibition of DNA topoisomerase II1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Antitumor agents. 120. New 4-substituted benzylamine and benzyl ether derivatives of 4'-O-demethylepipodophyllotoxin as potent inhibitors of human DNA topoisomerase II.
AID492484Cytotoxicity against human KB cells after 72 hrs by MTT assay2010Journal of natural products, Mar-26, Volume: 73, Issue:3
Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.
AID243343Percentage of protein-linked DNA breaks in KB cells by [3H]thymidine incorporation2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Antitumor agents. 234. Design, synthesis, and biological evaluation of novel 4beta-[(4' '-benzamido)-amino]-4'-o-demethyl-epipodophyllotoxin derivatives.
AID96351Concentration required for 50% reduction in KB cell number after 3-day incubation1992Journal of medicinal chemistry, Mar-06, Volume: 35, Issue:5
Antitumor agents. 124. New 4 beta-substituted aniline derivatives of 6,7-O,O-demethylene-4'-O-demethylpodophyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II.
AID211320Stimulation of in vitro Topoisomerase II-Linked DNA Complex Formation and Interference with Etoposide-Induced Cleavage at concentration 50 uM1996Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7
Antitumor agents. 164. Podophenazine, 2'',3''-dichloropodophenazine, benzopodophenazine, and their 4 beta-p-nitroaniline derivatives as novel DNA topoisomerase II inhibitors.
AID95512Compound was evaluated for cytotoxicity against KB cells at 10 uM concentration2004Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11
Antitumor agents. Part 230: C4'-esters of GL-331 as cytotoxic agents and DNA topoisomerase II inhibitors.
AID94330Effective dose of compound against replication of KB/7d cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID492485Cytotoxicity against human KB1 cells after 72 hrs by MTT assay2010Journal of natural products, Mar-26, Volume: 73, Issue:3
Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.
AID52064Inhibition of cellular protein-DNA complex formation at 10 uM1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Antitumor agents. 113. New 4 beta-arylamino derivatives of 4'-O-demethylepipodophyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II.
AID95650Effective dose of compound against replication of KB cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID667141Cytotoxicity against human A549 cells by SRB assay2012Bioorganic & medicinal chemistry letters, Jul-01, Volume: 22, Issue:13
Synthesis and evaluation of novel podophyllotoxin analogs.
AID96350Concentration required for 50% reduction in KB cell number after 3-day incubation1992Journal of medicinal chemistry, Mar-06, Volume: 35, Issue:5
Antitumor agents. 123. Synthesis and human DNA topoisomerase II inhibitory activity of 2'-chloro derivatives of etoposide and 4 beta-(arylamino)-4'-O-demethylpodophyllotoxins.
AID96044Cellular protein-DNA complex breaking activity against KB cells labeled with tritiated thymidine.1999Journal of medicinal chemistry, Jul-01, Volume: 42, Issue:13
Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4'-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles.
AID230161The differential toxicity ratio was defined as IC50(KB/7d)/IC50(KB)1996Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7
Antitumor agents. 164. Podophenazine, 2'',3''-dichloropodophenazine, benzopodophenazine, and their 4 beta-p-nitroaniline derivatives as novel DNA topoisomerase II inhibitors.
AID9244GI values against A549 cells (lung cancer)2001Journal of medicinal chemistry, Apr-26, Volume: 44, Issue:9
Antitumor agents. 207. Design, synthesis, and biological testing of 4beta-anilino-2-fluoro-4'-demethylpodophyllotoxin analogues as cytotoxic and antiviral agents.
AID246904Dose required to cause reduction in human nasopharyngeal KB cancer cells after 3 days incubation2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Antitumor agents. 234. Design, synthesis, and biological evaluation of novel 4beta-[(4' '-benzamido)-amino]-4'-o-demethyl-epipodophyllotoxin derivatives.
AID492487Cytotoxicity against human vincristine-resistant KB cells after 72 hrs by MTT assay2010Journal of natural products, Mar-26, Volume: 73, Issue:3
Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.
AID53299Compound was evaluated for the inhibition of human DNA Topoisomerase II1992Journal of medicinal chemistry, Mar-06, Volume: 35, Issue:5
Antitumor agents. 123. Synthesis and human DNA topoisomerase II inhibitory activity of 2'-chloro derivatives of etoposide and 4 beta-(arylamino)-4'-O-demethylpodophyllotoxins.
AID57205Inhibitory activity against human DNA topoisomerase II1990Journal of medicinal chemistry, Sep, Volume: 33, Issue:9
Antitumor agents. 113. New 4 beta-arylamino derivatives of 4'-O-demethylepipodophyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II.
AID243353Percentage of protein-linked DNA breaks in KB cells by [3H]thymidine incorporation at 5 ug/mL2004Journal of medicinal chemistry, Oct-07, Volume: 47, Issue:21
Antitumor agents. 234. Design, synthesis, and biological evaluation of novel 4beta-[(4' '-benzamido)-amino]-4'-o-demethyl-epipodophyllotoxin derivatives.
AID96032Lethal dose against KB cells when treated for 30 min2004Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11
Antitumor agents. Part 230: C4'-esters of GL-331 as cytotoxic agents and DNA topoisomerase II inhibitors.
AID335666Cytotoxicity against human KB cells assessed as reduction in cell number after 3 days1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 130, Novel 4 beta-arylamino derivatives of 3',4'-didemethoxy-3',4'-dioxo-4-deoxypodophyllotoxin as potent inhibitors of human DNA topoisomerase II.
AID214403Effective dose of compound against replication of U87MG cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
AID94011Lethal dose against KB-7d cells when treated for 30 min2004Bioorganic & medicinal chemistry letters, Jun-07, Volume: 14, Issue:11
Antitumor agents. Part 230: C4'-esters of GL-331 as cytotoxic agents and DNA topoisomerase II inhibitors.
AID52060Effect on cellular protein DNA complex formation(%) at 10 uM in comparison with etoposide1992Journal of medicinal chemistry, Mar-06, Volume: 35, Issue:5
Antitumor agents. 123. Synthesis and human DNA topoisomerase II inhibitory activity of 2'-chloro derivatives of etoposide and 4 beta-(arylamino)-4'-O-demethylpodophyllotoxins.
AID211458Compound tested for ability to form a cellular covalent topoisomerase II-DNA complex.1996Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7
Antitumor agents. 163. Three-dimensional quantitative structure-activity relationship study of 4'-O-demethylepipodophyllotoxin analogs using the modified CoMFA/q2-GRS approach.
AID335667Inhibition of human DNA topoisomerase 21992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 130, Novel 4 beta-arylamino derivatives of 3',4'-didemethoxy-3',4'-dioxo-4-deoxypodophyllotoxin as potent inhibitors of human DNA topoisomerase II.
AID1597989Inhibition of HIF-1alpha in human U373 cells2019Journal of medicinal chemistry, 06-27, Volume: 62, Issue:12
Small-Molecule Modulators of the Hypoxia-Inducible Factor Pathway: Development and Therapeutic Applications.
AID211319Stimulation of in vitro Topoisomerase II-Linked DNA Complex Formation and Interference with Etoposide-Induced Cleavage at concentration 1 uM; Not determined1996Journal of medicinal chemistry, Mar-29, Volume: 39, Issue:7
Antitumor agents. 164. Podophenazine, 2'',3''-dichloropodophenazine, benzopodophenazine, and their 4 beta-p-nitroaniline derivatives as novel DNA topoisomerase II inhibitors.
AID78823The compound was tested for tumor cell growth inhibitory activity against human ileocecal carcinoma (HCT-8) cell line1999Journal of medicinal chemistry, Jul-01, Volume: 42, Issue:13
Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4'-O-demethyl-podophyllotoxin and related compounds with improved pharmacological profiles.
AID94322Effective dose of compound against replication of KB-Vin cell line was evaluated2004Bioorganic & medicinal chemistry letters, Mar-22, Volume: 14, Issue:6
Antitumor agents. Part 232: Synthesis of cyclosulfite podophyllotoxin analogues as novel prototype antitumor agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's9 (34.62)18.2507
2000's12 (46.15)29.6817
2010's4 (15.38)24.3611
2020's1 (3.85)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.60

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 Index22.60 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.60)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (3.57%)5.53%
Reviews3 (10.71%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]