Literature DB >> 22169633

N-4-t-Butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure-activity relationships in the A-region.

Yong Soo Kim1, Min-Jung Kil, Sang-Uk Kang, HyungChul Ryu, Myeong Seop Kim, Yongsung Cho, Rahul S Bhondwe, Shivaji A Thorat, Wei Sun, Keliang Liu, Jin Hee Lee, Sun Choi, Larry V Pearce, Vladimir A Pavlyukovets, Matthew A Morgan, Richard Tran, Jozsef Lazar, Peter M Blumberg, Jeewoo Lee.   

Abstract

Structure-activity relationships for the A-region in a series of N-4-t-butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamides as TRPV1 antagonists have been investigated. Among them, the 3-fluoro analogue 54 showed high binding affinity and potent antagonism for both rTRPV1 and hTRPV1 in CHO cells. Its stereospecific activity was demonstrated with marked selectivity for the (S)-configuration (54S versus 54R). A docking study of 54S with our hTRPV1 homology model highlighted crucial hydrogen bonds between the ligand and the receptor contributing to its potency.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID： 22169633      PMCID： PMC3729215          DOI： 10.1016/j.bmc.2011.11.008

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


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