Page last updated: 2024-08-02 16:23:47

6-chlorotacrine

Description

6-chlorotacrine: structure given in first source [MeSH]

Cross-References

ID SourceID
PubMed CID10399068
CHEMBL ID292314
SCHEMBL ID4271238
MeSH IDM0258010

Synonyms (19)

Synonym
6-chloro-1,2,3,4-tetrahydroacridin-9-amine
6-chlorotacrine
bdbm8987
6-chlorotacrine.hcl
CHEMBL292314
6-chlorotacrine hcl
GQZMDBQRGRRPMS-UHFFFAOYSA-N
6-chloro-1,2,3,4-tetrahydro-acridin-9-ylamine
SCHEMBL4271238
5778-84-7
9-amino-6-chloro-1,2,3,4-tetrahydro-acridine
6-chloro-1,2,3,4-tetrahydro-9-acridinamine
C5T9A4VHZ8 ,
9-acridinamine, 6-chloro-1,2,3,4-tetrahydro-
6-chloranyl-1,2,3,4-tetrahydroacridin-9-amine
CS-0102398
F79838
unii-c5t9a4vhz8
PD083362

Protein Targets (10)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC500.0510AID1193209; AID1656477
CholinesteraseHomo sapiens (human)IC500.8458AID1183275; AID1384004; AID1511113; AID1545293; AID1593211; AID1721442; AID1763915; AID1799184; AID1831859; AID1904771
Muscarinic acetylcholine receptor M1Homo sapiens (human)IC506.0900AID1384006
AcetylcholinesteraseMus musculus (house mouse)IC500.0198AID1904773
AcetylcholinesteraseHomo sapiens (human)IC500.0535AID1166373; AID1183274; AID1193210; AID1256880; AID1384003; AID1511112; AID1545292; AID1593210; AID1721441; AID1763914; AID1796272; AID1799184; AID1831860; AID1904770; AID243154; AID243159; AID31017; AID31767; AID482894; AID654174
Acetylcholinesterase Bos taurus (cattle)IC500.3100AID1799184
Trypanothione reductaseTrypanosoma cruziKi80.0000AID214657
Bifunctional epoxide hydrolase 2Homo sapiens (human)IC5049.1160AID1904769
Bifunctional epoxide hydrolase 2Mus musculus (house mouse)IC5050.0000AID1904772
CholinesteraseEquus caballus (horse)IC500.0165AID1193211

Bioassays (86)

Assay IDTitleYearJournalArticle
AID1721441Inhibition of recombinant human AChE expressed in HEK293 cells using acetylthiocholine iodide as substrate preincubated for 15 mins followed by substrate addition by Ellman's method2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1545293Inhibition of human plasma butyrylcholinesterase using butyrylthiocholine iodide as substrate preincubated for 5 mins followed by substrate addition and measured after 15 mins by Ellman's method2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
ISSN: 1464-3391
Anti-cholinesterase hybrids as multi-target-directed ligands against Alzheimer's disease (1998-2018).
AID1656477Inhibition of electric eel AChE using acetylthiocholine chloride as substrate peincubated for 15 mins followed by substrate addition measured at 1 min interval by Ellman's method2020Bioorganic & medicinal chemistry letters, 02-01, Volume: 30, Issue:3
ISSN: 1464-3405
Propargylamine-derived multi-target directed ligands for Alzheimer's disease therapy.
AID1593220Cytotoxicity against human HepG2 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay2019European journal of medicinal chemistry, Apr-15, Volume: 168ISSN: 1768-3254Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease.
AID1721442Inhibition of recombinant human BChE using butyrylthiocholine iodide as substrate preincubated for 15 mins followed by substrate addition by Ellman's method2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1129463Neuroprotective activity in mouse HT22 cells assessed as protection against glutamate-induced oxidative damage after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
ISSN: 1464-3405
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID1384003Inhibition of human erythrocyte AChE using acetylthiocholine iodide as substrate preincubated for 5 mins followed by substrate addition measured at 2 mins time interval by Ellman's method2018European journal of medicinal chemistry, Apr-25, Volume: 150ISSN: 1768-3254The concept of hybrid molecules of tacrine and benzyl quinolone carboxylic acid (BQCA) as multifunctional agents for Alzheimer's disease.
AID1166376Inhibition of amyloid beta (1-42) self-mediated aggregation (unknown origin) at 10 uM after 24 hrs by thioflavin T fluorescence method2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804
Multitarget drug design strategy: quinone-tacrine hybrids designed to block amyloid-β aggregation and to exert anticholinesterase and antioxidant effects.
AID1721515Drug level in human liver microsomes treated with N-{8-[(6-Chloro-1,2,3,4-tetrahydroacridin-9-yl)amino]octyl}-2-(6-hydroxy-7-methoxy-2-methylchroman-2-yl)acetamide at 5 uM measured up to 60 mins by UPLC-MS/MS analysis2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1763919Inhibition of recombinant human nNOS assessed as maximum inhibition relative to control2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43ISSN: 1464-3405Huprine Y - Tryptophan heterodimers with potential implication to Alzheimer's disease treatment.
AID1721455Inhibition of self-induced Amyloid beta (1 to 42 residues) (unknown origin) aggregation expressed in Escherichia coli BL21 (DE3) at 10 uM measured after overnight incubation by thioflavin-S based spectrophotometric method relative to control2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1129462Cytotoxicity against mouse HT22 cells after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
ISSN: 1464-3405
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID1593210Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate preincubated for 5 mins followed by substrate addition and measured over 2 mins by UV-Vis spectrophotometric analysis based Ellman's method2019European journal of medicinal chemistry, Apr-15, Volume: 168ISSN: 1768-3254Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease.
AID1193213Antioxidant activity assessed as Trolox equivalent per microM of compound after 15 mins by oxygen radical absorbance capacity fluorescein assay2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1256881Hepatotoxicity in human HepG2 cells assessed as cell viability after 24 hrs by MTT assay2015Journal of medicinal chemistry, Nov-25, Volume: 58, Issue:22
ISSN: 1520-4804
Tacrine-Trolox Hybrids: A Novel Class of Centrally Active, Nonhepatotoxic Multi-Target-Directed Ligands Exerting Anticholinesterase and Antioxidant Activities with Low In Vivo Toxicity.
AID1183277Inhibition of aggregation of tau protein (unknown origin) expressed in Escherichia coli BL21 (DE3) assessed as amyloid fibril formation at 10 uM after 24 hrs by thioflavin S fluorescence method2014European journal of medicinal chemistry, Sep-12, Volume: 84ISSN: 1768-3254Tetrahydrobenzo[h][1,6]naphthyridine-6-chlorotacrine hybrids as a new family of anti-Alzheimer agents targeting β-amyloid, tau, and cholinesterase pathologies.
AID1256893Acute toxicity in im dosed albino Wistar rat assessed as mortality measured within 48 hrs2015Journal of medicinal chemistry, Nov-25, Volume: 58, Issue:22
ISSN: 1520-4804
Tacrine-Trolox Hybrids: A Novel Class of Centrally Active, Nonhepatotoxic Multi-Target-Directed Ligands Exerting Anticholinesterase and Antioxidant Activities with Low In Vivo Toxicity.
AID1183276Inhibition of aggregation of amyloid beta-42 (unknown origin) expressed in Escherichia coli BL21 (DE3) assessed as amyloid fibril formation at 10 uM after 24 hrs by thioflavin S fluorescence method2014European journal of medicinal chemistry, Sep-12, Volume: 84ISSN: 1768-3254Tetrahydrobenzo[h][1,6]naphthyridine-6-chlorotacrine hybrids as a new family of anti-Alzheimer agents targeting β-amyloid, tau, and cholinesterase pathologies.
AID243154Inhibitory activity against human erythrocyte acetylcholinesterase2004Journal of medicinal chemistry, Aug-26, Volume: 47, Issue:18
ISSN: 0022-2623
Modulation of binding strength in several classes of active site inhibitors of acetylcholinesterase studied by comparative binding energy analysis.
AID1904772Inhibition of recombinant mouse sEH using CMNPC as substrate preincubated for 5 mins followed by substrate addition and measured every 30 sec for 10 mins for by fluorescence based assay2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
ISSN: 1520-4804
Discovery and In Vivo Proof of Concept of a Highly Potent Dual Inhibitor of Soluble Epoxide Hydrolase and Acetylcholinesterase for the Treatment of Alzheimer's Disease.
AID1487761Selectivity index, ratio of IC50 for mouse J774.1 cells to IC50 for Trypanosoma brucei brucei TC221 measured after 48 hrs2017Bioorganic & medicinal chemistry, 08-15, Volume: 25, Issue:16
ISSN: 1464-3391
Bistacrines as potential antitrypanosomal agents.
AID1183275Inhibition of human recombinant BChE using butyrylthiocholine iodide as substrate by spectrophotometric analysis2014European journal of medicinal chemistry, Sep-12, Volume: 84ISSN: 1768-3254Tetrahydrobenzo[h][1,6]naphthyridine-6-chlorotacrine hybrids as a new family of anti-Alzheimer agents targeting β-amyloid, tau, and cholinesterase pathologies.
AID1831860Inhibition of recombinant human AChE using acetylthiocholine iodide as substrate preincubated for 20 mins followed by substrate addition by Ellman's method2021Journal of medicinal chemistry, 04-22, Volume: 64, Issue:8
ISSN: 1520-4804
Sustainable Drug Discovery of Multi-Target-Directed Ligands for Alzheimer's Disease.
AID1129464Ratio of EC50 for cytotoxicity against mouse HT22 cells to EC50 for neuroprotective activity in glutamate-induced mouse HT22 cells2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
ISSN: 1464-3405
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID1763916Selectivity index, ratio of IC50 for human BuchE to IC50 for human Ache2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43ISSN: 1464-3405Huprine Y - Tryptophan heterodimers with potential implication to Alzheimer's disease treatment.
AID1545292Inhibition of human erythrocyte acetylcholinesterase using acetylthiocholine as substrate preincubated for 5 mins followed by substrate addition by Ellman's method2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
ISSN: 1464-3391
Anti-cholinesterase hybrids as multi-target-directed ligands against Alzheimer's disease (1998-2018).
AID1437793Inhibition of amyloid beta 42 (unknown origin) self aggregation at 50 uM by ThT-based fluorometric method relative to control2017European journal of medicinal chemistry, Feb-15, Volume: 127ISSN: 1768-3254Tacrine-resveratrol fused hybrids as multi-target-directed ligands against Alzheimer's disease.
AID1511116Inhibition of human recombinant amyloid beta (1 to 42) aggregation expressed in Escherichia coli BL21 (DE3) at 10 uM by Thioflavin S steady state fluorescence assay relative to control2019European journal of medicinal chemistry, Oct-15, Volume: 180ISSN: 1768-3254A novel class of multitarget anti-Alzheimer benzohomoadamantane‒chlorotacrine hybrids modulating cholinesterases and glutamate NMDA receptors.
AID1166375Selectivity ratio of IC50 for human plasmatic BChE to human recombinant AChE2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804
Multitarget drug design strategy: quinone-tacrine hybrids designed to block amyloid-β aggregation and to exert anticholinesterase and antioxidant effects.
AID1193211Inhibition of equine serum BChE using acetylthiocholine chloride as substrate after 15 mins by Ellman spectrophotometric method2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1511118Permeability of the compound measured after compound dilution in PBS/EtOH buffer (70:30) by PAMPA-BBB assay2019European journal of medicinal chemistry, Oct-15, Volume: 180ISSN: 1768-3254A novel class of multitarget anti-Alzheimer benzohomoadamantane‒chlorotacrine hybrids modulating cholinesterases and glutamate NMDA receptors.
AID1256880Inhibition of human recombinant AChE using acetylthiocholine as substrate preincubated for 5 mins followed by substrate addition measured every 2 mins by Ellman's method2015Journal of medicinal chemistry, Nov-25, Volume: 58, Issue:22
ISSN: 1520-4804
Tacrine-Trolox Hybrids: A Novel Class of Centrally Active, Nonhepatotoxic Multi-Target-Directed Ligands Exerting Anticholinesterase and Antioxidant Activities with Low In Vivo Toxicity.
AID1193209Inhibition of electric eel AChE using acetylthiocholine chloride as substrate after 15 mins by Ellman spectrophotometric method2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1256878Selectivity ratio of IC50 for human plasmatic BChE to IC50 for human recombinant AChE2015Journal of medicinal chemistry, Nov-25, Volume: 58, Issue:22
ISSN: 1520-4804
Tacrine-Trolox Hybrids: A Novel Class of Centrally Active, Nonhepatotoxic Multi-Target-Directed Ligands Exerting Anticholinesterase and Antioxidant Activities with Low In Vivo Toxicity.
AID1593211Inhibition of human recombinant BChE using butyrylthiocholine iodide as substrate preincubated for 5 mins followed by substrate addition and measured over 2 mins by UV-Vis spectrophotometric analysis based Ellman's method2019European journal of medicinal chemistry, Apr-15, Volume: 168ISSN: 1768-3254Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease.
AID1904773Inhibition of recombinant mouse AChE using acetylthiocholine iodide as substrate preincubated for 20 mins followed by substrate addition and measured every 240 sec by Ellman's method2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
ISSN: 1520-4804
Discovery and In Vivo Proof of Concept of a Highly Potent Dual Inhibitor of Soluble Epoxide Hydrolase and Acetylcholinesterase for the Treatment of Alzheimer's Disease.
AID1545294Selectivity index, ratio of IC50 for human plasma butyrylcholinesterase to IC50 for human erythrocyte acetylcholinesterase2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
ISSN: 1464-3391
Anti-cholinesterase hybrids as multi-target-directed ligands against Alzheimer's disease (1998-2018).
AID1166373Inhibition of human recombinant AChE after 5 mins by Ellman method2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804
Multitarget drug design strategy: quinone-tacrine hybrids designed to block amyloid-β aggregation and to exert anticholinesterase and antioxidant effects.
AID31017Inhibitory activity against human erythrocyte acetylcholinesterase2000Journal of medicinal chemistry, May-18, Volume: 43, Issue:10
ISSN: 0022-2623
SAR of 9-amino-1,2,3,4-tetrahydroacridine-based acetylcholinesterase inhibitors: synthesis, enzyme inhibitory activity, QSAR, and structure-based CoMFA of tacrine analogues.
AID1193212Selectivity index, ratio of IC50 for equine serum BChE to IC50 for electric eel AChE2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1721454Inhibition human BACE1 expressed in baculovirus expression system at 5 uM using Panvera peptide as substrate measured after 60 mins by fluorescence assay relative to control2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1593213Inhibition of HFIP pretreated amyloid beta (1-42) (unknown origin) self aggregation at 50 uM incubated for 24 hrs by thioflavin T based fluorescence assay relative to control2019European journal of medicinal chemistry, Apr-15, Volume: 168ISSN: 1768-3254Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease.
AID1721453Inhibition human BACE1 expressed in baculovirus expression system using Panvera peptide as substrate measured after 60 mins by fluorescence assay2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1721447Potency index, ratio of 6-chlorotacrine IC50 to test compound IC50 for recombinant human BChE2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1193214Inhibition of self-induced Abeta(1 to 42) (unknown origin) aggregation at 25 uM after 24 hrs by Thioflavin T-based fluorometric assay2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID1511113Inhibition of human serum BChE using butyrylthiocholine iodide as substrate preincubated for 20 mins followed by substrate addition by spectrophotometry analysis2019European journal of medicinal chemistry, Oct-15, Volume: 180ISSN: 1768-3254A novel class of multitarget anti-Alzheimer benzohomoadamantane‒chlorotacrine hybrids modulating cholinesterases and glutamate NMDA receptors.
AID654174Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate preincubated for 20 mins prior substrate addition measured after 5 mins by spectrophotometry2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
ISSN: 1520-4804
Huprine-tacrine heterodimers as anti-amyloidogenic compounds of potential interest against Alzheimer's and prion diseases.
AID1487758Antitrypanosomal activity against Trypanosoma brucei brucei TC221 after 72 hrs by alamar blue assay2017Bioorganic & medicinal chemistry, 08-15, Volume: 25, Issue:16
ISSN: 1464-3391
Bistacrines as potential antitrypanosomal agents.
AID1721516Drug level in mouse liver microsomes treated with N-{8-[(6-Chloro-1,2,3,4-tetrahydroacridin-9-yl)amino]octyl}-2-(6-hydroxy-7-methoxy-2-methylchroman-2-yl)acetamide at 5 uM measured up to 60 mins by UPLC-MS/MS analysis2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1763914Inhibition of recombinant human AChE using acetylthiocholine as substrate by DTNB-reagent based Ellman's method2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43ISSN: 1464-3405Huprine Y - Tryptophan heterodimers with potential implication to Alzheimer's disease treatment.
AID31767Experimental pIC50 values for the inhibition of acetylcholinesterase2000Journal of medicinal chemistry, May-18, Volume: 43, Issue:10
ISSN: 0022-2623
SAR of 9-amino-1,2,3,4-tetrahydroacridine-based acetylcholinesterase inhibitors: synthesis, enzyme inhibitory activity, QSAR, and structure-based CoMFA of tacrine analogues.
AID1721457Permeability of compound in PBS/EtOH buffer (7:3) PAMPA-BBB assay2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID482894Inhibition of AChE2010European journal of medicinal chemistry, Mar, Volume: 45, Issue:3
ISSN: 1768-3254
Prediction of acetylcholinesterase inhibitors and characterization of correlative molecular descriptors by machine learning methods.
AID1593219Cytotoxicity against CHOK1 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay2019European journal of medicinal chemistry, Apr-15, Volume: 168ISSN: 1768-3254Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease.
AID1129472Antioxidant activity assessed as trolox equivalent of ABTS radical scavenging activity2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
ISSN: 1464-3405
Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species.
AID1763917Cytotoxicity against human HepG2 cells assessed as reduction in cell viability measured after 24 hrs by MTT assay2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43ISSN: 1464-3405Huprine Y - Tryptophan heterodimers with potential implication to Alzheimer's disease treatment.
AID1721456Inhibition of tau aggregation (unknown origin) expressed in Escherichia coli BL21 (DE3) at 10 uM measured after overnight incubation by thioflavin-S based spectrophotometric method relative to control2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1511117Inhibition of tau aggregation (unknown origin) expressed in Escherichia coli BL21 (DE3) at 10 uM by Thioflavin S steady state fluorescence assay relative to control2019European journal of medicinal chemistry, Oct-15, Volume: 180ISSN: 1768-3254A novel class of multitarget anti-Alzheimer benzohomoadamantane‒chlorotacrine hybrids modulating cholinesterases and glutamate NMDA receptors.
AID1721452Antioxidant activity assessed as DPPH radical scavenging activity incubated for 1 hr under dark condition2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1256875Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by microplate reader analysis2015Journal of medicinal chemistry, Nov-25, Volume: 58, Issue:22
ISSN: 1520-4804
Tacrine-Trolox Hybrids: A Novel Class of Centrally Active, Nonhepatotoxic Multi-Target-Directed Ligands Exerting Anticholinesterase and Antioxidant Activities with Low In Vivo Toxicity.
AID1763918Inhibition of recombinant human nNOS2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43ISSN: 1464-3405Huprine Y - Tryptophan heterodimers with potential implication to Alzheimer's disease treatment.
AID1511112Inhibition of human recombinant AChE expressed in HEK293 cells using acetylthiocholine iodide as substrate preincubated for 20 mins followed by substrate addition by spectrophotometry analysis2019European journal of medicinal chemistry, Oct-15, Volume: 180ISSN: 1768-3254A novel class of multitarget anti-Alzheimer benzohomoadamantane‒chlorotacrine hybrids modulating cholinesterases and glutamate NMDA receptors.
AID1384011Cytotoxicity against human HepG2 cells assessed as reduction in cell viability after 24 hrs by MTT assay2018European journal of medicinal chemistry, Apr-25, Volume: 150ISSN: 1768-3254The concept of hybrid molecules of tacrine and benzyl quinolone carboxylic acid (BQCA) as multifunctional agents for Alzheimer's disease.
AID1487760Cytotoxicity against mouse J774.1 cells after 24 hrs by alamar blue assay2017Bioorganic & medicinal chemistry, 08-15, Volume: 25, Issue:16
ISSN: 1464-3391
Bistacrines as potential antitrypanosomal agents.
AID1193210Inhibition of human erythrocyte AChE using acetylthiocholine chloride as substrate after 15 mins by Ellman spectrophotometric method2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405
Design, synthesis and evaluation of novel 5,6,7-trimethoxyflavone-6-chlorotacrine hybrids as potential multifunctional agents for the treatment of Alzheimer's disease.
AID214657The competitive inhibitory activity against trypanothione reductase was evaluated from Lineweaver Burk plots1999Journal of medicinal chemistry, Dec-30, Volume: 42, Issue:26
ISSN: 0022-2623
Inhibition of Trypanosoma cruzi trypanothione reductase by acridines: kinetic studies and structure-activity relationships.
AID243159In vitro inhibitory activity against human erythrocyte acetylcholinesterase2004Journal of medicinal chemistry, Aug-26, Volume: 47, Issue:18
ISSN: 0022-2623
Modulation of binding strength in several classes of active site inhibitors of acetylcholinesterase studied by comparative binding energy analysis.
AID1904769Inhibition of recombinant human sEH using CMNPC as substrate preincubated for 5 mins followed by substrate addition and measured every 30 sec for 10 mins for by fluorescence based assay2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
ISSN: 1520-4804
Discovery and In Vivo Proof of Concept of a Highly Potent Dual Inhibitor of Soluble Epoxide Hydrolase and Acetylcholinesterase for the Treatment of Alzheimer's Disease.
AID1593212Selectivity index, ratio of IC50 for recombinant human BChE to IC50 for recombinant human AChE2019European journal of medicinal chemistry, Apr-15, Volume: 168ISSN: 1768-3254Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease.
AID1256879Inhibition of human plasmatic BChE using butyrylthiocholine as substrate preincubated for 5 mins followed by substrate addition measured every 2 mins by Ellman's method2015Journal of medicinal chemistry, Nov-25, Volume: 58, Issue:22
ISSN: 1520-4804
Tacrine-Trolox Hybrids: A Novel Class of Centrally Active, Nonhepatotoxic Multi-Target-Directed Ligands Exerting Anticholinesterase and Antioxidant Activities with Low In Vivo Toxicity.
AID1763915Inhibition of recombinant human BuChE using butyrylthiocholine as substrate by Ellman's method2021Bioorganic & medicinal chemistry letters, 07-01, Volume: 43ISSN: 1464-3405Huprine Y - Tryptophan heterodimers with potential implication to Alzheimer's disease treatment.
AID1166374Inhibition of human plasmatic BChE after 5 mins by Ellman method2014Journal of medicinal chemistry, Oct-23, Volume: 57, Issue:20
ISSN: 1520-4804
Multitarget drug design strategy: quinone-tacrine hybrids designed to block amyloid-β aggregation and to exert anticholinesterase and antioxidant effects.
AID1511114Antagonist activity at NMDA receptor in rat CGN cells assessed as increase in intracellular calcium level incubated for 30 mins in presence of Fura-2AM followed by NMDA/glycine stimulation by fluorescence spectrometer analysis2019European journal of medicinal chemistry, Oct-15, Volume: 180ISSN: 1768-3254A novel class of multitarget anti-Alzheimer benzohomoadamantane‒chlorotacrine hybrids modulating cholinesterases and glutamate NMDA receptors.
AID1904771Inhibition of human recombinant BChE using butyrylthiocholine iodide as substrate preincubated for 20 mins followed by substrate addition and measured every 240 sec by Ellman's method2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
ISSN: 1520-4804
Discovery and In Vivo Proof of Concept of a Highly Potent Dual Inhibitor of Soluble Epoxide Hydrolase and Acetylcholinesterase for the Treatment of Alzheimer's Disease.
AID1384004Inhibition of human plasmatic BuChE using butyrylthiocholine iodide as substrate preincubated for 5 mins followed by substrate addition measured at 2 mins time interval by Ellman's method2018European journal of medicinal chemistry, Apr-25, Volume: 150ISSN: 1768-3254The concept of hybrid molecules of tacrine and benzyl quinolone carboxylic acid (BQCA) as multifunctional agents for Alzheimer's disease.
AID1511121Inhibition of human recombinant BACE-1 expressed in baculovirus expression system at 5 uM using panvera peptide as substrate measured after 1 hr by FRET assay relative to control2019European journal of medicinal chemistry, Oct-15, Volume: 180ISSN: 1768-3254A novel class of multitarget anti-Alzheimer benzohomoadamantane‒chlorotacrine hybrids modulating cholinesterases and glutamate NMDA receptors.
AID1384006Antagonist activity at human M1 mAChR expressed in CHO cells assessed as inhibition of oxotremorine M-stimulated calcium influx preincubated for 10 mins followed by oxotremorine M addition by Fluo-4 NW dye based fluorescence assay2018European journal of medicinal chemistry, Apr-25, Volume: 150ISSN: 1768-3254The concept of hybrid molecules of tacrine and benzyl quinolone carboxylic acid (BQCA) as multifunctional agents for Alzheimer's disease.
AID1593215Effective permeability of the compound in PBS buffer at pH 7.4 at 100 uM after 3 to 6 hrs by PAMPA2019European journal of medicinal chemistry, Apr-15, Volume: 168ISSN: 1768-3254Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease.
AID1384005Selectivity ratio of IC50 for human plasmatic BuChE to IC50 for human erythrocyte AChE2018European journal of medicinal chemistry, Apr-25, Volume: 150ISSN: 1768-3254The concept of hybrid molecules of tacrine and benzyl quinolone carboxylic acid (BQCA) as multifunctional agents for Alzheimer's disease.
AID1183274Inhibition of human recombinant AChE using acetylthiocholine iodide as substrate by spectrophotometric analysis2014European journal of medicinal chemistry, Sep-12, Volume: 84ISSN: 1768-3254Tetrahydrobenzo[h][1,6]naphthyridine-6-chlorotacrine hybrids as a new family of anti-Alzheimer agents targeting β-amyloid, tau, and cholinesterase pathologies.
AID1904770Inhibition of recombinant human AChE using acetylthiocholine iodide as substrate preincubated for 20 mins followed by substrate addition and measured every 240 sec by Ellman's method2022Journal of medicinal chemistry, 03-24, Volume: 65, Issue:6
ISSN: 1520-4804
Discovery and In Vivo Proof of Concept of a Highly Potent Dual Inhibitor of Soluble Epoxide Hydrolase and Acetylcholinesterase for the Treatment of Alzheimer's Disease.
AID1487759Antitrypanosomal activity against Trypanosoma brucei brucei TC221 after 48 hrs by alamar blue assay2017Bioorganic & medicinal chemistry, 08-15, Volume: 25, Issue:16
ISSN: 1464-3391
Bistacrines as potential antitrypanosomal agents.
AID1831859Inhibition of human serum BChE using butyrylthiocholine iodide as substrate preincubated for 20 mins followed by substrate addition by Ellman's method2021Journal of medicinal chemistry, 04-22, Volume: 64, Issue:8
ISSN: 1520-4804
Sustainable Drug Discovery of Multi-Target-Directed Ligands for Alzheimer's Disease.
AID1721517Drug level in rat liver microsomes treated with N-{8-[(6-Chloro-1,2,3,4-tetrahydroacridin-9-yl)amino]octyl}-2-(6-hydroxy-7-methoxy-2-methylchroman-2-yl)acetamide at 5 uM measured up to 60 mins by UPLC-MS/MS analysis2020Journal of medicinal chemistry, 09-10, Volume: 63, Issue:17
ISSN: 1520-4804
Centrally Active Multitarget Anti-Alzheimer Agents Derived from the Antioxidant Lead CR-6.
AID1799184AChE Inhibition Assay from Article 10.1021/jm900859q: \\Pyrano[3,2-c]quinoline-6-chlorotacrine hybrids as a novel family of acetylcholinesterase- and beta-amyloid-directed anti-Alzheimer compounds.\\2009Journal of medicinal chemistry, Sep-10, Volume: 52, Issue:17
ISSN: 1520-4804
Pyrano[3,2-c]quinoline-6-chlorotacrine hybrids as a novel family of acetylcholinesterase- and beta-amyloid-directed anti-Alzheimer compounds.
AID1796272AChE Inhibition Assay from Article 10.1021/jm990971t: \\SAR of 9-amino-1,2,3,4-tetrahydroacridine-based acetylcholinesterase inhibitors: synthesis, enzyme inhibitory activity, QSAR, and structure-based CoMFA of tacrine analogues.\\2000Journal of medicinal chemistry, May-18, Volume: 43, Issue:10
ISSN: 0022-2623
SAR of 9-amino-1,2,3,4-tetrahydroacridine-based acetylcholinesterase inhibitors: synthesis, enzyme inhibitory activity, QSAR, and structure-based CoMFA of tacrine analogues.

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (7.41)18.2507
2000's4 (14.81)29.6817
2010's16 (59.26)24.3611
2020's5 (18.52)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (7.14%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (92.86%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
quinacrineacridines;
aromatic ether;
organochlorine compound;
tertiary amino compound
antimalarial;
EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor
1999201417.5low001010
7-nitroindazole201920195.0low000010
tacrineacridines;
aromatic amine
EC 3.1.1.7 (acetylcholinesterase) inhibitor199920219.9medium0022102
atenololethanolamines;
monocarboxylic acid amide;
propanolamine
anti-arrhythmia drug;
antihypertensive agent;
beta-adrenergic antagonist;
environmental contaminant;
sympatholytic agent;
xenobiotic
201820186.0low000010
caffeinepurine alkaloid;
trimethylxanthine
adenosine A2A receptor antagonist;
adenosine receptor antagonist;
adjuvant;
central nervous system stimulant;
diuretic;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
environmental contaminant;
food additive;
fungal metabolite;
geroprotector;
human blood serum metabolite;
mouse metabolite;
mutagen;
plant metabolite;
psychotropic drug;
ryanodine receptor agonist;
xenobiotic
2009200915.0low000100
verapamilaromatic ether;
nitrile;
polyether;
tertiary amino compound
2009201910.0low000120
chlorpromazineorganochlorine compound;
phenothiazines;
tertiary amine
anticoronaviral agent;
antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
phenothiazine antipsychotic drug
2009201810.5low000110
cimetidinealiphatic sulfide;
guanidines;
imidazoles;
nitrile
adjuvant;
analgesic;
anti-ulcer drug;
H2-receptor antagonist;
P450 inhibitor
201420197.5low000020
clebopridepiperidines2010201014.0low000100
clonidineclonidine;
imidazoline
2009201910.0low000120
desipraminedibenzoazepine;
secondary amino compound
adrenergic uptake inhibitor;
alpha-adrenergic antagonist;
antidepressant;
cholinergic antagonist;
drug allergen;
EC 3.1.4.12 (sphingomyelin phosphodiesterase) inhibitor;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
H1-receptor antagonist;
serotonin uptake inhibitor
200920199.0low000130
donepezilaromatic ether;
indanones;
piperidines;
racemate
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
nootropic agent
201020216.2low000141
enoxacin1,8-naphthyridine derivative;
amino acid;
fluoroquinolone antibiotic;
monocarboxylic acid;
N-arylpiperazine;
quinolone antibiotic
antibacterial drug;
DNA synthesis inhibitor
2009200915.0low000100
fluoxetine(trifluoromethyl)benzenes;
aromatic ether;
secondary amino compound
2010201014.0low000100
furosemidechlorobenzoic acid;
furans;
sulfonamide
environmental contaminant;
loop diuretic;
xenobiotic
202120213.0low000001
huprine x2004200420.0low000100
imipraminedibenzoazepineadrenergic uptake inhibitor;
antidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
200920199.0low000130
lomefloxacinfluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone
antimicrobial agent;
antitubercular agent;
photosensitizing agent
2009201910.0low000120
memantineadamantanes;
primary aliphatic amine
antidepressant;
antiparkinson drug;
dopaminergic agent;
neuroprotective agent;
NMDA receptor antagonist
201920195.0low000010
minaprinemorpholines;
pyridazines;
secondary amine
antidepressant;
antiparkinson drug;
cholinergic drug;
dopamine uptake inhibitor;
serotonin uptake inhibitor
2010201014.0low000100
norfloxacinfluoroquinolone antibiotic;
N-arylpiperazine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone
antibacterial drug;
DNA synthesis inhibitor;
environmental contaminant;
xenobiotic
201420197.5low000020
ofloxacin3-oxo monocarboxylic acid;
N-arylpiperazine;
N-methylpiperazine;
organofluorine compound;
oxazinoquinoline
2009201910.0low000120
pentamidinearomatic ether;
carboxamidine;
diether
anti-inflammatory agent;
antifungal agent;
calmodulin antagonist;
chemokine receptor 5 antagonist;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
NMDA receptor antagonist;
S100 calcium-binding protein B inhibitor;
trypanocidal drug;
xenobiotic
201720177.0low000010
promazinephenothiazines;
tertiary amine
antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
H1-receptor antagonist;
muscarinic antagonist;
phenothiazine antipsychotic drug;
serotonergic antagonist
200920199.0low000130
propidiumphenanthridines;
quaternary ammonium ion
fluorochrome;
intercalator
2009200915.0low000100
corticosterone11beta-hydroxy steroid;
20-oxo steroid;
21-hydroxy steroid;
3-oxo-Delta(4) steroid;
C21-steroid;
glucocorticoid;
primary alpha-hydroxy ketone
human metabolite;
mouse metabolite
2009201910.0low000120
anilineanilines;
primary arylamine
2014201410.0low000010
tryptophanerythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan
antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
201920195.0low000010
n,n'-diphenyl-4-phenylenediamineN-substituted diamine;
secondary amino compound
antioxidant2014201410.0low000010
aminacrineaminoacridines;
primary amino compound
acid-base indicator;
antiinfective agent;
antiseptic drug;
fluorescent dye;
MALDI matrix material;
mutagen
1999201417.5low001010
4-aminodiphenylaminearomatic amine;
secondary amino compound
allergen2014201410.0low000010
4-phenylenediaminephenylenediamineallergen;
dye;
hapten;
reagent
2014201410.0low000010
galantaminebenzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound
antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite
201920195.0low000010
acetylcysteineacetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid
antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
201720177.0low000010
9-amino-6-chloro-2-methoxyacridine1999201417.5low001010
imidocarbureasantiprotozoal drug2010201014.0low000100
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acidchromanol;
monocarboxylic acid;
phenols
antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
201520206.7low000030
sr 951912010201014.0medium000100
rivastigminecarbamate ester;
tertiary amino compound
cholinergic drug;
EC 3.1.1.8 (cholinesterase) inhibitor;
neuroprotective agent
201920204.5low000020
7-chloro-4-aminoquinolineaminoquinoline2014201410.0low000010
propidium iodideorganic iodide salt2009201213.7medium000210
7-methoxytacrine201420216.1medium000052
anacardic acidhydroxy monocarboxylic acid;
hydroxybenzoic acid
anti-inflammatory agent;
antibacterial agent;
anticoronaviral agent;
apoptosis inducer;
EC 2.3.1.48 (histone acetyltransferase) inhibitor;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor;
neuroprotective agent;
plant metabolite
202120213.0low000001
zanapezilpiperidines2010201014.0high000100
tv3326indanes201920204.5medium000020
2-(4-hydroxyphenyl)-5,6,7-trimethoxy-4H-1-benzopyran-4-onemonohydroxyflavone;
trimethoxyflavone
201520159.0high000010
resveratrolresveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger
201720177.0low000010
1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid201820186.0low000010
ranitidineC-nitro compound;
furans;
organic sulfide;
tertiary amino compound
anti-ulcer drug;
drug allergen;
environmental contaminant;
H2-receptor antagonist;
xenobiotic
202120213.0low000001
quercetin7-hydroxyflavonol;
pentahydroxyflavone
antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
2014201410.0low000010
myricetin7-hydroxyflavonol;
hexahydroxyflavone
antineoplastic agent;
antioxidant;
cyclooxygenase 1 inhibitor;
food component;
geroprotector;
hypoglycemic agent;
plant metabolite
202120213.0low000001
ciproxifanaromatic ketone201920195.0low000010
vilazodone1-benzofurans;
indoles;
monocarboxylic acid amide;
N-alkylpiperazine;
N-arylpiperazine;
nitrile
antidepressant;
serotonergic agonist;
serotonin uptake inhibitor
201920195.0low000010
bis(7)-tacrinesecondary amino compoundapoptosis inhibitor;
EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
neuroprotective agent
200920199.7high000240
memoquin2014201410.0low000010
caproctamine2010201014.0low000100
huprine y2004201912.5low000110
xanthostigmine2010201014.0medium000100
ass234201920204.5high000020
piroxicambenzothiazine;
monocarboxylic acid amide;
pyridines
analgesic;
antirheumatic drug;
cyclooxygenase 1 inhibitor;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-steroidal anti-inflammatory drug
200920199.0low000130
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
tacrineacridines;
aromatic amine
EC 3.1.1.7 (acetylcholinesterase) inhibitor1996201912.0low001240
memantineadamantanes;
primary aliphatic amine
antidepressant;
antiparkinson drug;
dopaminergic agent;
neuroprotective agent;
NMDA receptor antagonist
201920195.0low000010
adamantaneadamantanes;
polycyclic alkane
201920195.0low000010
glutamic acidglutamic acid;
glutamine family amino acid;
L-alpha-amino acid;
proteinogenic amino acid
Escherichia coli metabolite;
ferroptosis inducer;
micronutrient;
mouse metabolite;
neurotransmitter;
nutraceutical
201920195.0low000010
scutellaringlucosiduronic acid;
glycosyloxyflavone;
monosaccharide derivative;
trihydroxyflavone
antineoplastic agent;
proteasome inhibitor
201720177.0low000010
apigenintrihydroxyflavoneantineoplastic agent;
metabolite
201720177.0low000010
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Acute Confusional Senile Dementia0200620227.1high0002123
African Sleeping Sickness0201720177.0low000010
Alzheimer Disease0200620227.1high0002123
Dementias, Transmissible02012201212.0low000010
Disease Models, Animal0202220222.0low000001
Tauopathies02014201410.0low000010
Trypanosomiasis, African0201720177.0low000010

Safety/Toxicity (1)

ArticleYear
Tacrine-Trolox Hybrids: A Novel Class of Centrally Active, Nonhepatotoxic Multi-Target-Directed Ligands Exerting Anticholinesterase and Antioxidant Activities with Low In Vivo Toxicity.
Journal of medicinal chemistry, , Nov-25, Volume: 58, Issue:22
2015