Discovery of 1-(1H-indazol-4-yl)-3-((1-phenyl-1H-pyrazol-5-yl)methyl) ureas as potent and thermoneutral TRPV1 antagonists.


Journal

Bioorganic & medicinal chemistry letters
ISSN: 1464-3405
Titre abrégé: Bioorg Med Chem Lett
Pays: England
ID NLM: 9107377

Informations de publication

Date de publication:
01 12 2020
Historique:
received: 21 07 2020
revised: 03 09 2020
accepted: 06 09 2020
pubmed: 16 9 2020
medline: 3 7 2021
entrez: 15 9 2020
Statut: ppublish

Résumé

A series of 1-indazol-3-(1-phenylpyrazol-5-yl)methyl ureas were investigated as hTRPV1 antagonists. The structure-activity relationship study was conducted systematically for both the indazole A-region and the 3-trifluoromethyl/t-butyl pyrazole C-region to optimize the antagonism toward the activation by capsaicin. Among them, the antagonists 26, 50 and 51 displayed highly potent antagonism with K

Identifiants

pubmed: 32931910
pii: S0960-894X(20)30659-4
doi: 10.1016/j.bmcl.2020.127548
pii:
doi:

Substances chimiques

Analgesics 0
Indazoles 0
Methylurea Compounds 0
Pyrazoles 0
TRPV Cation Channels 0
TRPV1 protein, human 0
Capsaicin S07O44R1ZM

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

127548

Informations de copyright

Copyright © 2020 Elsevier Ltd. All rights reserved.

Auteurs

Jin Mi Kang (JM)

Laboratory of Medicinal Chemistry, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.

Sun Ok Kwon (SO)

Laboratory of Medicinal Chemistry, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.

Jihyae Ann (J)

Laboratory of Medicinal Chemistry, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.

Peter M Blumberg (PM)

Laboratory of Medicinal Chemistry, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.

Heejin Ha (H)

Medifron DBT, Seoul 08502, Republic of Korea.

Young Dong Yoo (YD)

Medifron DBT, Seoul 08502, Republic of Korea.

Robert Frank-Foltyn (R)

Grünenthal Innovation, Grünenthal GmbH, D-52078 Aachen, Germany.

Bernhard Lesch (B)

Grünenthal Innovation, Grünenthal GmbH, D-52078 Aachen, Germany.

Gregor Bahrenberg (G)

Grünenthal Innovation, Grünenthal GmbH, D-52078 Aachen, Germany.

Hannelore Stockhausen (H)

Grünenthal Innovation, Grünenthal GmbH, D-52078 Aachen, Germany.

Thomas Christoph (T)

Grünenthal Innovation, Grünenthal GmbH, D-52078 Aachen, Germany.

Jeewoo Lee (J)

Laboratory of Medicinal Chemistry, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea. Electronic address: jeewoo@snu.ac.kr.

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Classifications MeSH