Literature DB >> 25659771

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

HyungChul Ryu1, Sejin Seo1, Jee-Young Lee1, Tae-Hwan Ha1, Sunho Lee1, Aeran Jung1, Jihyae Ann1, Sung-Eun Kim1, Suyoung Yoon1, Mannkyu Hong1, Peter M Blumberg2, Robert Frank-Foltyn3, Gregor Bahrenberg3, Klaus Schiene3, Hannelore Stockhausen3, Thomas Christoph3, Sven Frormann3, Jeewoo Lee4.   

Abstract

A series of pyridine derivatives in the C-region of N-((6-trifluoromethyl-pyridin-3-yl)methyl) 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides were investigated as hTRPV1 antagonists. The SAR analysis indicated that 6-difluorochloromethyl pyridine derivatives were the best surrogates of the C-region for previous leads. Among them, compound 31 showed excellent antagonism to capsaicin as well as to multiple hTRPV1 activators. It demonstrated strong analgesic activity in the formalin test in mice with full efficacy and it blocked capsaicin-induced hypothermia in vivo.
Copyright © 2015 Elsevier Masson SAS. All rights reserved.

Entities:  

Keywords:  Analgesic; TRPV1 antagonists; Vanilloid receptor 1

Mesh：

Substances：

Year:  2015        PMID： 25659771      PMCID： PMC6959515          DOI： 10.1016/j.ejmech.2015.02.001

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN： 0223-5234            Impact factor:   6.514


  23 in total

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Journal:  Brain Res Rev       Date:  2008-12-25

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

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Journal:  Neuron       Date:  1998-09       Impact factor: 17.173

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

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Journal:  Pain       Date:  1977-12       Impact factor: 6.961

Review 8.  Transient receptor potential vanilloid-1 antagonists: a survey of recent patent literature.

Authors:  Eric A Voight; Michael E Kort
Journal:  Expert Opin Ther Pat       Date:  2010-09       Impact factor: 6.674

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

10.  2-Aryl substituted pyridine C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as highly potent TRPV1 antagonists.

Authors:  HyungChul Ryu; Sejin Seo; Myeong Seop Kim; Mi-Yeon Kim; Ho Shin Kim; Jihyae Ann; Phuong-Thao Tran; Van-Hai Hoang; Jieun Byun; Minghua Cui; Karam Son; Pankaz Kumar Sharma; Sun Choi; Peter M Blumberg; Robert Frank-Foltyn; Gregor Bahrenberg; Babette-Yvonne Koegel; Thomas Christoph; Sven Frormann; Jeewoo Lee
Journal:  Bioorg Med Chem Lett       Date:  2014-06-02       Impact factor: 2.823
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  5 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.  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

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

Authors:  Jihyae Ann; Yooran Ki; Suyoung Yoon; Myeong Seop Kim; Jung-Un Lee; Changhoon Kim; Sunho Lee; Aeran Jung; Jisoo Baek; Sunhye Hong; Sun Choi; Larry V Pearce; Timothy E Esch; Noe A Turcios; Nancy E Lewin; Adebowale E Ogunjirin; Brienna K A Herold; Anna K McCall; Peter M Blumberg; Jeewoo Lee
Journal:  Bioorg Med Chem       Date:  2016-01-28       Impact factor: 3.641

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

Authors:  Jihyae Ann; Wei Sun; Xing Zhou; Aeran Jung; Jisoo Baek; Sunho Lee; Changhoon Kim; Suyoung Yoon; Sunhye Hong; Sun Choi; Noe A Turcios; Brienna K A Herold; Timothy E Esch; Nancy E Lewin; Adelle Abramovitz; Larry V Pearce; Peter M Blumberg; Jeewoo Lee
Journal:  Bioorg Med Chem Lett       Date:  2016-06-07       Impact factor: 2.823
  5 in total

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