| Asymmetric synthesis and biological evaluation of N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carboxamide as hCB1 receptor antagonists. | |
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MedLine Citation:
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PMID: 21937154 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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We recently discovered and reported a novel series of benzhydrylpiperazine derivatives bearing an asymmetric carbon atom that are potent and selective hCB1 inverse agonists. In the present study, we used Davis-Ellmann-type sulfonamide chemistry to asymmetrically synthesize two enantiomers of the most potent racemic N-cyclohexyl-4-[1-(2,4-dichlorophenyl)-1-(p-tolyl)methyl]piperazine-1-carbo-xamide [14]. Enantiomer separation and configuration assignment were carried out. Our results indicate that the R-configuration is the more active enantiomer, displaying enhanced antagonistic activity for hCB1 receptor, better oral bioavailability, and greater efficacy in the reduction of body weight in diet-induced obese mice. |
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Authors:
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Linghuan Gao; Min Li; Tao Meng; Hongli Peng; Xin Xie; Yongliang Zhang; Yu Jin; Xin Wang; Libo Zou; Jingkang Shen |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-9-1 |
Journal Detail:
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Title: European journal of medicinal chemistry Volume: - ISSN: 1768-3254 ISO Abbreviation: - Publication Date: 2011 Sep |
Date Detail:
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Created Date: 2011-9-22 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 0420510 Medline TA: Eur J Med Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
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Copyright © 2011 Elsevier Masson SAS. All rights reserved. |
Affiliation:
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State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, PR China; Department of Pharmacology, School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shengyang 110016, PR China. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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