ArticleJournal of medicinal chemistry2006
Inhibition of human acetyl- and butyrylcholinesterase by novel carbamates of (-)- and (+)-tetrahydrofurobenzofuran and methanobenzodioxepine.
Article in Journal of medicinal chemistry, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 77 citations in OpenAlex.
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- Discovery of Novel Acetylcholinesterase Inhibitors as Potential Candidates for the Treatment of Alzheimer's Disease.International journal of molecular sciences · 2019Article
- In Silico Study Probes Potential Inhibitors of Human Dihydrofolate Reductase for Cancer Therapeutics.Journal of clinical medicine · 2019Article
- Pharmacophore-based design and discovery of (-)-meptazinol carbamates as dual modulators of cholinesterase and amyloidogenesis.Journal of enzyme inhibition and medicinal chemistry · 2017Article
- Acetylcholinesterase Inhibitors and Drugs Acting on Muscarinic Receptors- Potential Crosstalk of Cholinergic Mechanisms During Pharmacological Treatment.Current neuropharmacology · 2017Review
- Inhibition of acetylcholinesterase by two genistein derivatives: kinetic analysis, molecular docking and molecular dynamics simulation.Acta pharmaceutica Sinica. B · 2014Article
- Linking Alzheimer's disease and type 2 diabetes mellitus via aberrant insulin signaling and inflammation.CNS & neurological disorders drug targets · 2014Review
- The Concise Guide to PHARMACOLOGY 2013/14: enzymes.British journal of pharmacology · 2013Article
- Exploring different virtual screening strategies for acetylcholinesterase inhibitors.BioMed research international · 2013Article
- Synthesis of the Alzheimer drug Posiphen into its primary metabolic products (+)-N1-norPosiphen, (+)-N8-norPosiphen and (+)-N1, N8-bisnorPosiphen, their inhibition of amyloid precursor protein, α-Synuclein synthesis, interleukin-1β release, and cholinergic action.Anti-inflammatory & anti-allergy agents in medicinal chemistry · 2013Article
- Molecular docking and receptor-specific 3D-QSAR studies of acetylcholinesterase inhibitors.Molecular diversity · 2012Article
- Pharmacophore-based virtual screening and density functional theory approach to identifying novel butyrylcholinesterase inhibitors.Acta pharmacologica Sinica · 2012Article
- Structure-property relationships of a class of carbamate-based fatty acid amide hydrolase (FAAH) inhibitors: chemical and biological stability.ChemMedChem · 2009Article
- Tetrahydrofurobenzofuran cymserine, a potent butyrylcholinesterase inhibitor and experimental Alzheimer drug candidate, enzyme kinetic analysis.Journal of neural transmission (Vienna, Austria : 1996) · 2008Article
- Kinetics of human serum butyrylcholinesterase inhibition by a novel experimental Alzheimer therapeutic, dihydrobenzodioxepine cymserine.Neurochemical research · 2008Article
- Differential effects of two hexahydropyrroloindole carbamate-based anticholinesterase drugs on the amyloid beta protein pathway involved in Alzheimer's disease.Neuromolecular medicine · 2007Article
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Authors and funding
10 authors at 1 institution in 1 country.
Funding
Abstract
A new enantiomeric synthesis utilizing classical resolution provided two novel series of optically active inhibitors of cholinesterase: (-)- and (+)-O-carbamoyl phenols of tetrahydrofurobenzofuran and methanobenzodioxepine. An additional two series of (-)- and (+)-O-carbamoyl phenols of pyrroloindole and furoindole were obtained by known procedures, and their anticholinesterase actions were similarly quantified against freshly prepared human acetyl- (AChE) and butyrylcholinesterase (BChE). Both enantiomeric forms of each series demonstrated potent cholinesterase inhibitory activity (with IC(50) values as low as 10 nM for AChE and 3 nM for BChE), with the exception of the (+)-O-carbamoyl phenols of pyrroloindole, which lacked activity (IC(50) values >1 microM). Based on the biological data of these four series, a structure-activity relationship (SAR) analysis was provided by molecular volume calculations. In addition, a probable transition-state model was established according to the known X-ray structure of a transition-state complex of Torpedo californica AChE-m-(N,N,N-trimethylammonio)-2,2,2-trifluoroacetophenone (TcAChE-TMTFA). This model proved valuable in explaining the enantioselectivity and enzyme subtype selectivity of each series. These carbamates are more potent than, or similarly potent to, anticholinesterases in current clinical use, providing not only inhibitors of potential clinical relevance but also pharmacological tools to define drug-enzyme binding interactions within an enzyme crucial in the maintenance of cognition and numerous systemic physiological functions in health, aging, and disease.
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