Literature DB >> 24035514

TRPV1 antagonist with high analgesic efficacy: 2-Thio pyridine C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides.

Tae-Hwan Ha1, Hyungchul Ryu, Sung-Eun Kim, Ho Shin Kim, Jihyae Ann, Phuong-Thao Tran, Van-Hai Hoang, Karam Son, Minghua Cui, Sun Choi, Peter M Blumberg, Robert Frank, Gregor Bahrenberg, Klaus Schiene, Thomas Christoph, Sven Frormann, Jeewoo Lee.   

Abstract

A series of 2-thio pyridine C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides were investigated as hTRPV1 antagonists. Among them, compound 24S showed stereospecific and excellent TRPV1 antagonism of capsaicin-induced activation. Further, it demonstrated strong anti-allodynic in a rat neuropathic pain model. Consistent with its action in vitro being through TRPV1, compound 24S blocked capsaicin-induced hypothermia in mice. Docking analysis of 24S with our hTRPV1 homology model was performed to identify its binding mode.
Copyright © 2013 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Analgesic; Capsaicin; Resiniferatoxin; TRPV1 antagonists

Mesh：

Substances：

Year:  2013        PMID： 24035514      PMCID： PMC6957258          DOI： 10.1016/j.bmc.2013.08.015

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


  22 in total

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Journal:  J Comput Aided Mol Des       Date:  2011-03-30       Impact factor: 3.686

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Journal:  Trends Mol Med       Date:  2006-09-25       Impact factor: 11.951

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Journal:  Expert Opin Ther Pat       Date:  2010-09       Impact factor: 6.674

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Journal:  Pain       Date:  1988-04       Impact factor: 6.961
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  10 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.  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

3.  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

4.  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

5.  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

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

Authors:  HyungChul Ryu; Sejin Seo; Jee-Young Lee; Tae-Hwan Ha; Sunho Lee; Aeran Jung; Jihyae Ann; Sung-Eun Kim; Suyoung Yoon; Mannkyu Hong; Peter M Blumberg; Robert Frank-Foltyn; Gregor Bahrenberg; Klaus Schiene; Hannelore Stockhausen; Thomas Christoph; Sven Frormann; Jeewoo Lee
Journal:  Eur J Med Chem       Date:  2015-02-02       Impact factor: 6.514

7.  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

8.  2-Alkyl/alkenyl substituted pyridine C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as highly potent TRPV1 antagonists.

Authors:  HyungChul Ryu; Sejin Seo; Seong-Hee Cho; Ho Shin Kim; Aeran Jung; Dong Wook Kang; Karam Son; Minghua Cui; Sun-hye Hong; Pankaz Kumar Sharma; Sun Choi; Peter M Blumberg; Robert Frank-Foltyn; Gregor Bahrenberg; Hannelore Stockhausen; Klaus Schiene; Thomas Christoph; Sven Frormann; Jeewoo Lee
Journal:  Bioorg Med Chem Lett       Date:  2014-06-02       Impact factor: 2.823

9.  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

10.  A new era for the design of TRPV1 antagonists and agonists with the use of structural information and molecular docking of capsaicin-like compounds.

Authors:  Julio Caballero
Journal:  J Enzyme Inhib Med Chem       Date:  2022-12       Impact factor: 5.756
  10 in total

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