α-Substituted N-(4-tert-butylbenzyl)-N′-[4-(methylsulfonylamino)benzyl]thiourea analogues as potent and stereospecific TRPV1 antagonists

Jae Uk Chung, Su Yeon Kim, Ju Ok Lim, Hyun Kyung Choi, Sang Uk Kang, Hae Seok Yoon, Hyung Chul Ryu, Dong Wook Kang, Jeewoo Lee, Bomi Kang, Sun Choi, Attila Toth, Larry V. Pearce, Vladimir A. Pavlyukovets, Daniel J. Lundberg, Peter M. Blumberg

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25 Scopus citations

Abstract

A series of α-substituted N-(4-tert-butylbenzyl)-N′-[4-(methylsulfonylamino)benzyl]thiourea analogues have been investigated as TRPV1 receptor antagonists. α-Methyl substituted analogues showed potent and stereospecific antagonism to the action of capsaicin on rat TRPV1 heterologously expressed in Chinese hamster ovary cells. In particular, compounds 14 and 18, which possess the R-configuration, exhibited excellent potencies (respectively, Ki = 41 and 39.2 nM and Ki(ant) = 4.5 and 37 nM).

Original languageEnglish
Pages (from-to)6043-6053
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume15
Issue number18
DOIs
StatePublished - 15 Sep 2007

Keywords

  • Analgesic
  • TRPV1 antagonists

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