Page last updated: 2024-12-06

9-amino-6-chloro-2-methoxyacridine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID19080
CHEMBL ID76954
SCHEMBL ID106725
MeSH IDM0056691

Synonyms (38)

Synonym
BIDD:GT0515
CHEMBL76954
6-chloro-2-methoxy-9-acridinamine
5-amino-2-chloro-7-methoxyacridine (european)
9-amino-6-chloro-2-methoxyacridine
nsc 15300
brn 0226315
nsc15300
5-amino-2-chloro-7-methoxyacridine
acridine, 9-amino-3-chloro-7-methoxy-
3548-09-2
wln: t c666 bnj eg iz lo1
9-acridinamine, 6-chloro-2-methoxy-
g 185
nsc-15300
acridine, 9-amino-6-chloro-2-methoxy-
6-chloro-2-methoxy-acridin-9-amine
6-chloro-2-methoxyacridine-9-ylamine
9-amino-6-chloro-2-methoxyacridine, suitable for fluorescence, >=95%
bdbm24710
6-chloro-2-methoxyacridin-9-amine
acma
2-methoxy-6-chloro-9-aminoacridine
9-amino-2-methoxy-6-chloroacridine
9-amino-3-chloro-7-methoxyacridine
FT-0621611
SCHEMBL106725
IHHSSHCBRVYGJX-UHFFFAOYSA-N
DTXSID90188987
AKOS027381471
AS-61900
EX-A7409
D85361
CS-0065321
HY-118155
PD057853
R9EB8YPL49
g-185
[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)
Coagulation factor XIIHomo sapiens (human)Ki52.90000.00251.86697.2500AID1798464
AcetylcholinesteraseHomo sapiens (human)Ki0.04900.00001.27869.7300AID1798465
Liver carboxylesterase 1Homo sapiens (human)Ki52.90000.00252.01368.4800AID1798464
Trypanothione reductaseTrypanosoma cruziKi7.00000.07605.15297.6000AID214657
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
plasma kallikrein-kinin cascadeCoagulation factor XIIHomo sapiens (human)
Factor XII activationCoagulation factor XIIHomo sapiens (human)
blood coagulation, intrinsic pathwayCoagulation factor XIIHomo sapiens (human)
positive regulation of plasminogen activationCoagulation factor XIIHomo sapiens (human)
protein processingCoagulation factor XIIHomo sapiens (human)
protein autoprocessingCoagulation factor XIIHomo sapiens (human)
positive regulation of blood coagulationCoagulation factor XIIHomo sapiens (human)
zymogen activationCoagulation factor XIIHomo sapiens (human)
fibrinolysisCoagulation factor XIIHomo sapiens (human)
innate immune responseCoagulation factor XIIHomo sapiens (human)
response to misfolded proteinCoagulation factor XIIHomo sapiens (human)
positive regulation of fibrinolysisCoagulation factor XIIHomo sapiens (human)
blood coagulationCoagulation factor XIIHomo sapiens (human)
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
cholesterol biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
response to toxic substanceLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol effluxLiver carboxylesterase 1Homo sapiens (human)
negative regulation of cholesterol storageLiver carboxylesterase 1Homo sapiens (human)
epithelial cell differentiationLiver carboxylesterase 1Homo sapiens (human)
cholesterol homeostasisLiver carboxylesterase 1Homo sapiens (human)
reverse cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
medium-chain fatty acid metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid biosynthetic processLiver carboxylesterase 1Homo sapiens (human)
cellular response to cholesterolLiver carboxylesterase 1Homo sapiens (human)
cellular response to low-density lipoprotein particle stimulusLiver carboxylesterase 1Homo sapiens (human)
cholesterol ester hydrolysis involved in cholesterol transportLiver carboxylesterase 1Homo sapiens (human)
positive regulation of cholesterol metabolic processLiver carboxylesterase 1Homo sapiens (human)
regulation of bile acid secretionLiver carboxylesterase 1Homo sapiens (human)
lipid catabolic processLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityCoagulation factor XIIHomo sapiens (human)
calcium ion bindingCoagulation factor XIIHomo sapiens (human)
protein bindingCoagulation factor XIIHomo sapiens (human)
misfolded protein bindingCoagulation factor XIIHomo sapiens (human)
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
sterol esterase activityLiver carboxylesterase 1Homo sapiens (human)
methylumbelliferyl-acetate deacetylase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylesterase activityLiver carboxylesterase 1Homo sapiens (human)
carboxylic ester hydrolase activityLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (21)

Processvia Protein(s)Taxonomy
extracellular regionCoagulation factor XIIHomo sapiens (human)
extracellular spaceCoagulation factor XIIHomo sapiens (human)
plasma membraneCoagulation factor XIIHomo sapiens (human)
collagen-containing extracellular matrixCoagulation factor XIIHomo sapiens (human)
extracellular exosomeCoagulation factor XIIHomo sapiens (human)
extracellular spaceCoagulation factor XIIHomo sapiens (human)
rough endoplasmic reticulumCoagulation factor XIIHomo sapiens (human)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
cytoplasmLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulum lumenLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
cytosolLiver carboxylesterase 1Homo sapiens (human)
lipid dropletLiver carboxylesterase 1Homo sapiens (human)
endoplasmic reticulumLiver carboxylesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (35)

Assay IDTitleYearJournalArticle
AID1888339Competitive inhibition of human recombinant MGMT expressed in Escherichia coli STAR BL21 pRare cells assessed as cleavage of fluorescent labelled substrate by Bsp 119I at 12.5 uM using O6MeG-bearing substrate (S) incubated for 10 mins in presence of non-s
AID1888337Inhibition of human recombinant MGMT expressed in Escherichia coli STAR BL21 pRare cells assessed as cleavage of fluorescent labelled substrate by Bsp 119I at 12.5 uM using O6MeG-bearing substrate (S) incubated for 5 mins by coupled enzymatic analysis rel
AID1888334Binding affinity to calf thymus DNA assessed as ligand-induced thermal stabilization of DNA duplex by measuring change in melting temperature at 6.25 uM by thermal denaturation analysis
AID1888344Antiproliferative activity against human Panel NCI-60 (60 carcinoma cell lines) assessed as cell growth inhibition incubated for 48 hrs
AID1129471Neuroprotective activity in glutamate-induced mouse HT22 cells assessed as decrease in mitochondrial ROS level at 1 uM after 12 hrs by D123-based flow cytometric analysis2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID1888365Synergistic antiproliferative activity against human T98G cells assessed as reduction in cell viability at GI50 pretreated for 2 hrs followed by TMZ addition at 94 uM and measured after 94 hrs by CellTiter-Glo luminescent cell viability assay
AID1888333Binding affinity to calf thymus DNA assessed as intercalation by measuring dissociation constant at 20 uM measured after 5 mins by UV-Vis spectrophotometric titration analysis
AID344303Antiprion activity against human prion Fukuoka-1 infected mouse F3 cells assessed as reduction of scrapie prion protein accumulation2008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
Antiprion activity of functionalized 9-aminoacridines related to quinacrine.
AID1888338Irreversible inhibition of human recombinant MGMT expressed in Escherichia coli STAR BL21 pRare cells assessed as cleavage of fluorescent labelled substrate by Bsp 119I at 12.5 uM using O6MeG-bearing substrate (S) preincubated for 30 mins followed by subs
AID1888383Fluorescence property of compound in THF assessed as quantum yield
AID1129473Antioxidant activity assessed as trolox equivalent of ABTS radical scavenging activity up to 20 uM2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID1888370Additive antiproliferative activity against human T98G cells assessed as reduction in cell viability at GI50 pretreated for 2 hrs followed by TMZ addition at 188 uM and measured after 94 hrs by CellTiter-Glo luminescent cell viability assay
AID695925Inhibition of HIV-1 reverse transcriptase using Poly(rA).p(dT) (12 to 18) as substrate after 30 mins by single point PCR assay2012Bioorganic & medicinal chemistry letters, Jul-15, Volume: 22, Issue:14
Inhibition of therapeutically important polymerases with high affinity bis-intercalators.
AID693226Effective permeability of the compound at pH 7.4 at 30 to 50 uM by PAMPA assay2011European journal of medicinal chemistry, Jul, Volume: 46, Issue:7
Anti-prion activities and drug-like potential of functionalized quinacrine analogs with basic phenyl residues at the 9-amino position.
AID344304Antiprion activity against human prion Fukuoka-1 infected mouse F3 cells assessed as drug level required for more than 99 percent reduction of scrapie prion protein2008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
Antiprion activity of functionalized 9-aminoacridines related to quinacrine.
AID214657The competitive inhibitory activity against trypanothione reductase was evaluated from Lineweaver Burk plots1999Journal of medicinal chemistry, Dec-30, Volume: 42, Issue:26
Inhibition of Trypanosoma cruzi trypanothione reductase by acridines: kinetic studies and structure-activity relationships.
AID1129469Neuroprotective activity in glutamate-induced mouse HT22 cells assessed as elevation of GSH level at 1 uM after 12 hrs by Ellman's method relative to control2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID1888385Fluorescence property of compound in aqueous solution assessed as quantum yield
AID1888382Fluorescence property of compound in MeCN assessed as quantum yield
AID1129462Cytotoxicity against mouse HT22 cells after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID693225Binding affinity to truncated human PrP 121-231 at 50 uM by surface plasmon resonance method2011European journal of medicinal chemistry, Jul, Volume: 46, Issue:7
Anti-prion activities and drug-like potential of functionalized quinacrine analogs with basic phenyl residues at the 9-amino position.
AID1129466Neuroprotective activity in glutamate-induced mouse HT22 cells assessed as decrease in intracellular calcium level at 1 uM after 12 hrs by Fluo-3-AM-based fluorescence analysis2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID344295Antiprion activity against scrapie prion protein RML infected mouse ScN2a cells assessed as reduction of scrapie prion protein accumulation by immunoblot analysis2008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
Antiprion activity of functionalized 9-aminoacridines related to quinacrine.
AID25809Ionization state of the molecule at physiological pH was evaluated by potentiometry. 1999Bioorganic & medicinal chemistry letters, Jan-18, Volume: 9, Issue:2
Synthesis of an imidazo[1,2-e]purine-acridine heterodimer for targeting abasic sites in DNA.
AID1888335Displacement of ethidium bromide from calf thymus DNA incubated for 30 mins by fluorescence microplate reader assay
AID1129465Neuroprotective activity in mouse HT22 cells assessed as protection against glutamate-induced oxidative damage at less than cytotoxic EC50 after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID1888341Antiproliferative activity against human T98G cells assessed as cell growth inhibition incubated for 96 hrs by CellTiter-Glo luminescent cell viability assay
AID344297Cytotoxicity against mouse ScN2a cells assessed as maximal tolerant concentration2008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
Antiprion activity of functionalized 9-aminoacridines related to quinacrine.
AID344298Selectivity index, ratio of maximal tolerant concentration for mouse ScN2a cells to EC50 for scrapie prion protein RML infected mouse ScN2a cells2008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
Antiprion activity of functionalized 9-aminoacridines related to quinacrine.
AID1888384Fluorescence property of compound in MeOH assessed as quantum yield
AID1888336Binding affinity to calf thymus DNA assessed as ligand induced positive CD band at 50 uM by Circular dichroism spectroscopy analysis
AID1129470Neuroprotective activity in glutamate-induced mouse HT22 cells assessed as decrease in ROS level at 1 uM after 12 hrs by H2DCF diacetate-based flow cytometric analysis2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID344296Antiprion activity against scrapie prion protein RML infected mouse ScN2a cells assessed as drug level required for more than 99 percent reduction of scrapie prion protein by immunoblot analysis2008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
Antiprion activity of functionalized 9-aminoacridines related to quinacrine.
AID1798465Cholinesterase Inhibition Assay from Article 10.1016/s1074-5521(03)00071-1: \\Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug tacrine: from binding promiscuity to selective inhibition.\\2003Chemistry & biology, Apr, Volume: 10, Issue:4
Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug tacrine: from binding promiscuity to selective inhibition.
AID1798464Enzyme Inhibition Assay from Article 10.1016/s1074-5521(03)00071-1: \\Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug tacrine: from binding promiscuity to selective inhibition.\\2003Chemistry & biology, Apr, Volume: 10, Issue:4
Crystal structure of human carboxylesterase 1 complexed with the Alzheimer's drug tacrine: from binding promiscuity to selective inhibition.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (53)

TimeframeStudies, This Drug (%)All Drugs %
pre-199014 (26.42)18.7374
1990's11 (20.75)18.2507
2000's17 (32.08)29.6817
2010's10 (18.87)24.3611
2020's1 (1.89)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.68

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 Index19.68 (24.57)
Research Supply Index4.06 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.68)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.75%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other56 (98.25%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]