Literature DB >> 27317643

Discovery of N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea as a potent TRPV1 antagonistic template.

Jihyae Ann1, Wei Sun2, Xing Zhou3, Aeran Jung1, Jisoo Baek1, Sunho Lee1, Changhoon Kim1, Suyoung Yoon1, Sunhye Hong4, Sun Choi4, Noe A Turcios5, Brienna K A Herold5, Timothy E Esch5, Nancy E Lewin5, Adelle Abramovitz5, Larry V Pearce5, Peter M Blumberg5, Jeewoo Lee6.   

Abstract

A series of homologous analogues of prototype antagonist 1 and its urea surrogate were investigated as hTRPV1 ligands. Through one-carbon elongation in the respective pharmacophoric regions, N-(3-fluoro-4-methylsulfonamidomethylphenyl)urea was identified as a novel and potent TRPV1 antagonistic template. Its representative compound 27 showed a potency comparable to that of lead compound 1. Docking analysis of compound 27 in our hTRPV1 homology model indicated that its binding mode was similar with that of 1S.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Analgesic; TRPV1 antagonists; Vanilloid receptor 1

Mesh：

Substances：

Year:  2016        PMID： 27317643      PMCID： PMC6957248          DOI： 10.1016/j.bmcl.2016.06.010

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  31 in total

Review 1.  Transient receptor potential vanilloid type 1 antagonists: a patent review (2011 - 2014).

Authors:  Yoonji Lee; Sunhye Hong; Minghua Cui; Pankaz K Sharma; Jeewoo Lee; Sun Choi
Journal:  Expert Opin Ther Pat       Date:  2015-03       Impact factor: 6.674

2.  Nickel-Catalyzed Direct Electrochemical Cross-Coupling between Aryl Halides and Activated Alkyl Halides.

Authors:  Muriel Durandetti; Jean-Yves Nédélec; Jacques Périchon
Journal:  J Org Chem       Date:  1996-03-08       Impact factor: 4.354

3.  Analgesic potential of TRPV1 antagonists.

Authors:  Philip R Kym; Michael E Kort; Charles W Hutchins
Journal:  Biochem Pharmacol       Date:  2009-03-05       Impact factor: 5.858

Review 4.  Therapeutic potential of vanilloid receptor TRPV1 agonists and antagonists as analgesics: Recent advances and setbacks.

Authors:  Gilbert Y Wong; Narender R Gavva
Journal:  Brain Res Rev       Date:  2008-12-25

Review 5.  Modulation of the TRPV1 channel: current clinical trials and recent patents with focus on neurological conditions.

Authors:  Luciano De Petrocellis; Aniello S Moriello
Journal:  Recent Pat CNS Drug Discov       Date:  2013-12

6.  α-Substituted 2-(3-fluoro-4-methylsulfonamidophenyl)acetamides as potent TRPV1 antagonists.

Authors:  Phuong-Thao Tran; Ho Shin Kim; Jihyae Ann; Sung-Eun Kim; Changhoon Kim; Mannkyu Hong; Van-Hai Hoang; Van T H Ngo; Sunhye Hong; Minghua Cui; Sun Choi; Peter M Blumberg; Robert Frank-Foltyn; Gregor Bahrenberg; Hannelore Stockhausen; Thomas Christoph; Jeewoo Lee
Journal:  Bioorg Med Chem Lett       Date:  2015-04-12       Impact factor: 2.823

7.  The cloned capsaicin receptor integrates multiple pain-producing stimuli.

Authors:  M Tominaga; M J Caterina; A B Malmberg; T A Rosen; H Gilbert; K Skinner; B E Raumann; A I Basbaum; D Julius
Journal:  Neuron       Date:  1998-09       Impact factor: 17.173

8.  Synthesis and biological evaluation of [¹¹C]SB366791: a new PET-radioligand for in vivo imaging of the TRPV1 receptor.

Authors:  Daisy van Veghel; Jan Cleynhens; Larry V Pearce; Peter M Blumberg; Koen Van Laere; Alfons Verbruggen; Guy Bormans
Journal:  Nucl Med Biol       Date:  2012-11-07       Impact factor: 2.408

Review 9.  Multisteric TRPV1 nocisensor: a target for analgesics.

Authors:  János Szolcsányi; Zoltán Sándor
Journal:  Trends Pharmacol Sci       Date:  2012-10-12       Impact factor: 14.819

Review 10.  Clinical development of TRPV1 antagonists: targeting a pivotal point in the pain pathway.

Authors:  Martin J Gunthorpe; Boris A Chizh
Journal:  Drug Discov Today       Date:  2008-12-26       Impact factor: 7.851
View more
  7 in total

1.  t-Butyl pyridine and phenyl C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists.

Authors:  Sunho Lee; Dong Wook Kang; HyungChul Ryu; Changhoon Kim; Jihyae Ann; Hobin Lee; Eunhye Kim; Sunhye Hong; Sun Choi; Peter M Blumberg; Robert Frank-Foltyn; Gregor Bahrenberg; Hannelore Stockhausen; Thomas Christoph; Jeewoo Lee
Journal:  Bioorg Med Chem       Date:  2017-03-06       Impact factor: 3.641

2.  Discovery of dual-acting opioid ligand and TRPV1 antagonists as novel therapeutic agents for pain.

Authors:  Hobin Lee; Songyeon Ahn; Jihyae Ann; Heejin Ha; Young Dong Yoo; Young Ho Kim; Ji-Young Hwang; Kwang-Hyun Hur; Choon-Gon Jang; Larry V Pearce; Timothy E Esch; Nancy E Lewin; Peter M Blumberg; Jeewoo Lee
Journal:  Eur J Med Chem       Date:  2019-08-21       Impact factor: 6.514

3.  Pyrazole C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as potent TRPV1 antagonists.

Authors:  Sunho Lee; Changhoon Kim; Jihyae Ann; Shivaji A Thorat; Eunhye Kim; Jongmi Park; Sun Choi; Peter M Blumberg; Robert Frank-Foltyn; Gregor Bahrenberg; Hannelore Stockhausen; Thomas Christoph; Jeewoo Lee
Journal:  Bioorg Med Chem Lett       Date:  2017-08-12       Impact factor: 2.823

4.  Novel Radiolabeled Vanilloid with Enhanced Specificity for Human Transient Receptor Potential Vanilloid 1 (TRPV1).

Authors:  Larry V Pearce; Jihyae Ann; Aeran Jung; Shivaji A Thorat; Brienna K A Herold; Amelework D Habtemichael; Peter M Blumberg; Jeewoo Lee
Journal:  J Med Chem       Date:  2017-09-21       Impact factor: 7.446

5.  TRPV1 antagonists that cause hypothermia, instead of hyperthermia, in rodents: Compounds' pharmacological profiles, in vivo targets, thermoeffectors recruited and implications for drug development.

Authors:  A Garami; E Pakai; H A McDonald; R M Reilly; A Gomtsyan; J J Corrigan; E Pinter; D X D Zhu; S G Lehto; N R Gavva; P R Kym; A A Romanovsky
Journal:  Acta Physiol (Oxf)       Date:  2018-02-16       Impact factor: 6.311

Review 6.  TRPV1: A Target for Rational Drug Design.

Authors:  Vincenzo Carnevale; Tibor Rohacs
Journal:  Pharmaceuticals (Basel)       Date:  2016-08-23

Review 7.  Cryo-EM as a powerful tool for drug discovery.

Authors:  John H Van Drie; Liang Tong
Journal:  Bioorg Med Chem Lett       Date:  2020-09-02       Impact factor: 2.823
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.