2-Sulfonamidopyridine C-region analogs of 2-(3-fluoro-4-methylsulfonamidophenyl)propanamides as potent TRPV1 antagonists

被引：10

作者：

Ann, Jihyae ^{[1
]}

Ki, Yooran ^{[1
]}

Yoon, Suyoung ^{[1
]}

Kim, Myeong Seop ^{[1
]}

Lee, Jung-Un ^{[1
]}

Kim, Changhoon ^{[1
]}

Lee, Sunho ^{[1
]}

Jung, Aeran ^{[1
]}

Baek, Jisoo ^{[1
]}

Hong, Sunhye ^{[2
]}

Choi, Sun ^{[2
]}

Pearce, Larry V. ^{[3
]}

Esch, Timothy E. ^{[3
]}

Turcios, Noe A. ^{[3
]}

Lewin, Nancy E. ^{[3
]}

Ogunjirin, Adebowale E. ^{[3
]}

Herold, Brienna K. A. ^{[3
]}

McCall, Anna K. ^{[3
]}

Blumberg, Peter M. ^{[3
]}

Lee, Jeewoo ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Pharm, Pharmaceut Sci Res Inst, Med Chem Lab, Seoul 151742, South Korea

[2] Ewha Womans Univ, Grad Sch Pharmaceut Sci, Coll Pharm, Natl Leading Res Lab Mol Modeling & Drug Design, Seoul 120750, South Korea

[3] NCI, Lab Canc Biol & Genet, Ctr Canc Res, NIH, Bethesda, MD 20892 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2016年 / 24卷 / 06期

关键词：

Vanilloid receptor 1; TRPV1; antagonists; Analgesic; VANILLOID CAPSAICIN RECEPTORS; ANALGESIC AGENTS; AGONIST ACTIVITY; FORMALIN TEST; 2-(3-FLUORO-4-METHYLSULFONYLAMINOPHENYL)PROPANAMIDES; ACTIVATION; DOCKING;

D O I：

10.1016/j.bmc.2016.01.051

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of 2-sulfonamidopyridine C-region derivatives of 2-(3-fluoro-4-methylsulfonamidophenyl)propanamide were investigated as hTRPV1 ligands. Systematic modification on the 2-sulfonamido group provided highly potent TRPV1 antagonists. The N-benzyl phenylsulfonamide derivatives 12 and 23 in particular showed higher affinities than that of lead compound 1. Compound 12 exhibited strong analgesic activity in the formalin pain model. Docking analysis of its chiral S-form 12S in our hTRPV1 homology model indicated that its high affinity might arise from additional hydrophobic interactions not present in lead compound 1S. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：1231 / 1240

页数：10

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