Literature DB >> 24794110

α-Methylated simplified resiniferatoxin (sRTX) thiourea analogues as potent and stereospecific TRPV1 antagonists.

Ho Shin Kim1, Mi-Kyoung Jin1, Sang-Uk Kang1, Ju-Ok Lim1, Phuong-Thao Tran1, Van-Hai Hoang1, Jihyae Ann1, Tae-Hwan Ha1, Larry V Pearce2, Vladimir A Pavlyukovets2, Peter M Blumberg2, Jeewoo Lee3.   

Abstract

A series of α-methylated analogues of the potent sRTX thiourea antagonists were investigated as rTRPV1 ligands in order to examine the effect of α-methylation on receptor activity. The SAR analysis indicated that activity was stereospecific with the (R)-configuration of the newly formed chiral center providing high binding affinity and potent antagonism while the configuration of the C-region was not significant.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

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

Mesh：

Substances：

Year:  2014        PMID： 24794110      PMCID： PMC6957243          DOI： 10.1016/j.bmcl.2014.04.054

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


  19 in total

1.  N-(3-Acyloxy-2-benzylpropyl)-N'-(4-hydroxy-3-methoxybenzyl) thiourea derivatives as potent vanilloid receptor agonists and analgesics.

Authors:  J Lee; J Lee; J Kim; S Y Kim; M W Chun; H Cho; S W Hwang; U Oh; Y H Park; V E Marquez; M Beheshti; T Szabo; P M Blumberg
Journal:  Bioorg Med Chem       Date:  2001-01       Impact factor: 3.641

Review 2.  Vanilloid (Capsaicin) receptors and mechanisms.

Authors:  A Szallasi; P M Blumberg
Journal:  Pharmacol Rev       Date:  1999-06       Impact factor: 25.468

3.  N-4-t-Butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure-activity relationships in the A-region.

Authors:  Yong Soo Kim; Min-Jung Kil; Sang-Uk Kang; HyungChul Ryu; Myeong Seop Kim; Yongsung Cho; Rahul S Bhondwe; Shivaji A Thorat; Wei Sun; Keliang Liu; Jin Hee Lee; Sun Choi; Larry V Pearce; Vladimir A Pavlyukovets; Matthew A Morgan; Richard Tran; Jozsef Lazar; Peter M Blumberg; Jeewoo Lee
Journal:  Bioorg Med Chem       Date:  2011-11-22       Impact factor: 3.641

4.  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 5.  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

6.  Asymmetric synthesis and receptor activity of chiral simplified resiniferatoxin (sRTX) analogues as transient receptor potential vanilloid 1 (TRPV1) ligands.

Authors:  Myeong Seop Kim; Yooran Ki; Song Yeon Ahn; Suyoung Yoon; Sung-Eun Kim; Hyeung-Geun Park; Wei Sun; Karam Son; Minghua Cui; Sun Choi; Larry V Pearce; Timothy E Esch; Ian A Deandrea-Lazarus; Peter M Blumberg; Jeewoo Lee
Journal:  Bioorg Med Chem Lett       Date:  2013-11-06       Impact factor: 2.823

7.  N-[4-(methylsulfonylamino)benzyl]thiourea analogues as vanilloid receptor antagonists: analysis of structure-activity relationships for the "C-Region".

Authors:  Jeewoo Lee; Sang-Uk Kang; Ju-Ok Lim; Hyun-Kyung Choi; Mi-kyung Jin; Attila Toth; Larry V Pearce; Richard Tran; Yun Wang; Tamas Szabo; Peter M Blumberg
Journal:  Bioorg Med Chem       Date:  2004-01-15       Impact factor: 3.641

8.  Capsazepine: a competitive antagonist of the sensory neurone excitant capsaicin.

Authors:  S Bevan; S Hothi; G Hughes; I F James; H P Rang; K Shah; C S Walpole; J C Yeats
Journal:  Br J Pharmacol       Date:  1992-10       Impact factor: 8.739

9.  Alpha-substituted N-(4-tert-butylbenzyl)-N'-[4-(methylsulfonylamino)benzyl]thiourea analogues as potent and stereospecific TRPV1 antagonists.

Authors:  Jae-Uk Chung; Su Yeon Kim; Ju-Ok Lim; Hyun-Kyung Choi; Sang-Uk Kang; Hae-Seok Yoon; Hyungchul Ryu; Dong Wook Kang; Jeewoo Lee; Bomi Kang; Sun Choi; Attila Toth; Larry V Pearce; Vladimir A Pavlyukovets; Daniel J Lundberg; Peter M Blumberg
Journal:  Bioorg Med Chem       Date:  2007-06-26       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
View more
  2 in total

1.  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

2.  Novel scaffolds for modulation of TRPV1 identified with pharmacophore modeling and virtual screening.

Authors:  Daria Goldmann; Peter Pakfeifer; Steffen Hering; Gerhard F Ecker
Journal:  Future Med Chem       Date:  2015       Impact factor: 4.767
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.