Literature DB >> 24948568

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

HyungChul Ryu1, Sejin Seo1, Seong-Hee Cho1, Ho Shin Kim1, Aeran Jung1, Dong Wook Kang2, Karam Son3, Minghua Cui3, Sun-hye Hong3, Pankaz Kumar Sharma3, Sun Choi3, Peter M Blumberg4, Robert Frank-Foltyn5, Gregor Bahrenberg5, Hannelore Stockhausen5, Klaus Schiene5, Thomas Christoph5, Sven Frormann5, Jeewoo Lee6.   

Abstract

A series of 2-alkyl/alkenyl pyridine C-region derivatives of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides were investigated as hTRPV1 antagonists. Multiple compounds showed excellent and stereospecific TRPV1 antagonism with better potency than previous lead 2. Among them, compound 15f demonstrated a strong analgesic profile in a rat neuropathic pain model and blocked capsaicin-induced hypothermia in a dose-dependent manner. Docking analysis of (S)-15f with our hTRPV1 homology model provided insight into its specific binding mode.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Capsaicin; Molecular modeling; Resiniferatoxin; TRPV1 antagonist; Vanilloid receptor 1

Mesh：

Substances：

Year:  2014        PMID： 24948568      PMCID： PMC6956567          DOI： 10.1016/j.bmcl.2014.05.074

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


  20 in total

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Journal:  Pharmacol Rev       Date:  1999-06       Impact factor: 25.468

2.  The capsaicin receptor: a heat-activated ion channel in the pain pathway.

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Journal:  Nature       Date:  1997-10-23       Impact factor: 49.962

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

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.  Structural insights into transient receptor potential vanilloid type 1 (TRPV1) from homology modeling, flexible docking, and mutational studies.

Authors:  Jin Hee Lee; Yoonji Lee; HyungChul Ryu; Dong Wook Kang; Jeewoo Lee; Jozsef Lazar; Larry V Pearce; Vladimir A Pavlyukovets; Peter M Blumberg; Sun Choi
Journal:  J Comput Aided Mol Des       Date:  2011-03-30       Impact factor: 3.686

Review 7.  TRPV1: a therapeutic target for novel analgesic drugs?

Authors:  Arpad Szallasi; Francisco Cruz; Pierangelo Geppetti
Journal:  Trends Mol Med       Date:  2006-09-25       Impact factor: 11.951

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

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

Authors:  Tae-Hwan Ha; 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
Journal:  Bioorg Med Chem       Date:  2013-08-13       Impact factor: 3.641

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
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  8 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.  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
  8 in total

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