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Rational design, synthesis, biological evaluation, homology and docking studies of coumarin derivatives as α1 -adrenoceptor antagonists. 2011

Xiang Zhou, and Ya-Dong Chen, and Tao Wang, and Xiao-Bing Wang, and Ling-Yi Kong
Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, 210009 Nanjing, P. R. China.

According to a three-point pharmacophore for some uro-selective α(1) -adrenoceptor (AR) antagonists, a novel class of coumarin (=2H-1-benzopyran-2-one) derivatives have been successfully designed and synthesized with high efficacies for α(1) -AR. These synthesized coumarin derivatives exhibited high efficacies towards α(1) -AR in in vitro pharmacological assays. Compared with prazosin (pK(i) value of 8.77), among those coumarins, tolylpiperazine-substituted derivatives, 7 and 8, have comparable pK(i) values of 8.81 and 8.77, respectively. The trend in efficacies of these coumarin derivatives towards α(1A) -adrenoceptor was further rationalized by intensive molecular docking. Our work demonstrated that the designed coumarin derivatives can inhibit α(1) -AR in vitro. These findings will provide a guide for further studies of the medical therapy of benign prostatic hyperplasia (BPH).

UI MeSH Term Description Entries
D003198 Computer Simulation Computer-based representation of physical systems and phenomena such as chemical processes. Computational Modeling,Computational Modelling,Computer Models,In silico Modeling,In silico Models,In silico Simulation,Models, Computer,Computerized Models,Computer Model,Computer Simulations,Computerized Model,In silico Model,Model, Computer,Model, Computerized,Model, In silico,Modeling, Computational,Modeling, In silico,Modelling, Computational,Simulation, Computer,Simulation, In silico,Simulations, Computer
D003374 Coumarins Synthetic or naturally occurring substances related to coumarin, the delta-lactone of coumarinic acid. 1,2-Benzopyrone Derivatives,1,2-Benzopyrones,Coumarin Derivative,Coumarine,1,2-Benzo-Pyrones,Benzopyran-2-ones,Coumarin Derivatives,Coumarines,1,2 Benzo Pyrones,1,2 Benzopyrone Derivatives,1,2 Benzopyrones,Benzopyran 2 ones,Derivative, Coumarin,Derivatives, 1,2-Benzopyrone,Derivatives, Coumarin
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D001665 Binding Sites The parts of a macromolecule that directly participate in its specific combination with another molecule. Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining
D015195 Drug Design The molecular designing of drugs for specific purposes (such as DNA-binding, enzyme inhibition, anti-cancer efficacy, etc.) based on knowledge of molecular properties such as activity of functional groups, molecular geometry, and electronic structure, and also on information cataloged on analogous molecules. Drug design is generally computer-assisted molecular modeling and does not include PHARMACOKINETICS, dosage analysis, or drug administration analysis. Computer-Aided Drug Design,Computerized Drug Design,Drug Modeling,Pharmaceutical Design,Computer Aided Drug Design,Computer-Aided Drug Designs,Computerized Drug Designs,Design, Pharmaceutical,Drug Design, Computer-Aided,Drug Design, Computerized,Drug Designs,Drug Modelings,Pharmaceutical Designs
D058668 Adrenergic alpha-1 Receptor Antagonists Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS. Adrenergic alpha-1 Antagonists,Adrenergic alpha-1 Receptor Blockers,Adrenergic alpha1-Antagonists,alpha-1 Adrenergic Blocking Agents,alpha1-Adrenergic Antagonists,alpha1-Adrenoceptor Blocker,Adrenergic alpha 1 Antagonists,Adrenergic alpha 1 Receptor Antagonists,Adrenergic alpha 1 Receptor Blockers,Adrenergic alpha1 Antagonists,Antagonists, alpha1-Adrenergic,alpha 1 Adrenergic Blocking Agents,alpha-1 Antagonists, Adrenergic,alpha1 Adrenergic Antagonists,alpha1 Adrenoceptor Blocker,alpha1-Antagonists, Adrenergic
D018340 Receptors, Adrenergic, alpha-1 A subclass of alpha-adrenergic receptors that mediate contraction of SMOOTH MUSCLE in a variety of tissues such as ARTERIOLES; VEINS; and the UTERUS. They are usually found on postsynaptic membranes and signal through GQ-G11 G-PROTEINS. Adrenergic alpha-1 Receptors,Receptors, alpha-1 Adrenergic,alpha-1 Adrenergic Receptors,Adrenergic Receptor, alpha-1,Adrenergic alpha-1A Receptors,Adrenergic alpha-1B Receptors,Adrenergic alpha-1D Receptors,Receptor, Adrenergic, alpha-1,Receptor, Adrenergic, alpha-1A,Receptor, Adrenergic, alpha-1B,Receptor, Adrenergic, alpha-1D,Receptors, Adrenergic, alpha-1A,Receptors, Adrenergic, alpha-1B,Receptors, Adrenergic, alpha-1D,alpha 1 Adrenergic Receptor,alpha-1A Adrenergic Receptor,alpha-1B Adrenergic Receptor,alpha-1C Adrenergic Receptor,alpha-1D Adrenergic Receptor,Adrenergic Receptor, alpha 1,Adrenergic Receptor, alpha-1A,Adrenergic Receptor, alpha-1B,Adrenergic Receptor, alpha-1C,Adrenergic Receptor, alpha-1D,Adrenergic Receptors, alpha-1,Adrenergic alpha 1 Receptors,Adrenergic alpha 1A Receptors,Adrenergic alpha 1B Receptors,Adrenergic alpha 1D Receptors,Receptor, alpha-1 Adrenergic,Receptor, alpha-1A Adrenergic,Receptor, alpha-1B Adrenergic,Receptor, alpha-1C Adrenergic,Receptor, alpha-1D Adrenergic,Receptors, Adrenergic alpha-1,Receptors, Adrenergic alpha-1A,Receptors, Adrenergic alpha-1B,Receptors, Adrenergic alpha-1D,Receptors, alpha 1 Adrenergic,alpha 1 Adrenergic Receptors,alpha 1A Adrenergic Receptor,alpha 1B Adrenergic Receptor,alpha 1C Adrenergic Receptor,alpha 1D Adrenergic Receptor,alpha-1 Adrenergic Receptor,alpha-1 Receptors, Adrenergic,alpha-1A Receptors, Adrenergic,alpha-1B Receptors, Adrenergic,alpha-1D Receptors, Adrenergic

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