Literature DB >> 26860926

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

Jihyae Ann1, Yooran Ki1, Suyoung Yoon1, Myeong Seop Kim1, Jung-Un Lee1, Changhoon Kim1, Sunho Lee1, Aeran Jung1, Jisoo Baek1, Sunhye Hong2, Sun Choi2, Larry V Pearce3, Timothy E Esch3, Noe A Turcios3, Nancy E Lewin3, Adebowale E Ogunjirin3, Brienna K A Herold3, Anna K McCall3, Peter M Blumberg3, Jeewoo Lee4.   

Abstract

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.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Analgesic; TRPV1 antagonists; Vanilloid receptor 1

Mesh：

Substances：

Year:  2016        PMID： 26860926      PMCID： PMC6957252          DOI： 10.1016/j.bmc.2016.01.051

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


  31 in total

1.  Structure activity relationships of benzyl C-region analogs of 2-(3-fluoro-4-methylsulfonamidophenyl)propanamides as potent TRPV1 antagonists.

Authors:  Jihyae Ann; Aeran Jung; Mi-Yeon Kim; Hyuk-Min Kim; HyungChul Ryu; Sunjoo Kim; Dong Wook Kang; Sunhye Hong; Minghua Cui; Sun Choi; Peter M Blumberg; Robert Frank-Foltyn; Gregor Bahrenberg; Hannelore Stockhausen; Thomas Christoph; Jeewoo Lee
Journal:  Bioorg Med Chem       Date:  2015-10-09       Impact factor: 3.641

2.  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 3.  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 4.  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

5.  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

6.  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

7.  The formalin test: a quantitative study of the analgesic effects of morphine, meperidine, and brain stem stimulation in rats and cats.

Authors:  David Dubuisson; Stephen G Dennis
Journal:  Pain       Date:  1977-12       Impact factor: 6.961

Review 8.  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 9.  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

10.  Contributions of different modes of TRPV1 activation to TRPV1 antagonist-induced hyperthermia.

Authors:  Andras Garami; Yury P Shimansky; Eszter Pakai; Daniela L Oliveira; Narender R Gavva; Andrej A Romanovsky
Journal:  J Neurosci       Date:  2010-01-27       Impact factor: 6.167
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  4 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.  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

3.  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 4.  TRPV1: A Target for Rational Drug Design.

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

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