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Literature DB >> 22796184

The SAR analysis of TRPV1 agonists with the α-methylated B-region.

Yongsung Cho¹, Myeong Seop Kim, Ho Shin Kim, Jihyae Ann, Jiyoun Lee, Larry V Pearce, Vladimir A Pavlyukovets, Matthew A Morgan, Peter M Blumberg, Jeewoo Lee.

Abstract

A series of TRPV1 agonists with amide, reverse amide, and thiourea groups in the B-region and their corresponding α-methylated analogues were investigated. Whereas the α-methylation of the amide B-region enhanced the binding affinities and potencies as agonists, that of the reverse amide and thiourea led to a reduction in receptor affinity. The analysis indicated that proper hydrogen bonding as well as steric effects in the B-region are critical for receptor binding.

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Year: 2012 PMID： 22796184 PMCID： PMC3799874 DOI： 10.1016/j.bmcl.2012.06.059

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

21 in total

1. 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

2. Analysis of structure-activity relationships for the 'A-region' of N-(4-t-butylbenzyl)-N'-[4-(methylsulfonylamino)benzyl]thiourea analogues as TRPV1 antagonists.

Authors: Jeewoo Lee; Sang-Uk Kang; Min-Jung Kil; Myoungyoup Shin; Ju-Ok Lim; Hyun-Kyung Choi; Mi-Kyoung Jin; Su Yeon Kim; Sung-Eun Kim; Yong-Sil Lee; Kyung-Hoon Min; Young-Ho Kim; Hee-Jin Ha; Richard Tran; Jacqueline D Welter; Yun Wang; Tamas Szabo; Larry V Pearce; Daniel J Lundberg; Attila Toth; Vladimir A Pavlyukovets; Matthew A Morgan; Peter M Blumberg
Journal: Bioorg Med Chem Lett Date: 2005-09-15 Impact factor: 2.823

Review 3. The potential of transient receptor potential vanilloid type 1 channel modulators for the treatment of pain.

Authors: Susan M Westaway
Journal: J Med Chem Date: 2007-05-10 Impact factor: 7.446

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

3. 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

3 in total

The SAR analysis of TRPV1 agonists with the α-methylated B-region.

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

2. Analysis of structure-activity relationships for the 'A-region' of N-(4-t-butylbenzyl)-N'-[4-(methylsulfonylamino)benzyl]thiourea analogues as TRPV1 antagonists.

Review 3. The potential of transient receptor potential vanilloid type 1 channel modulators for the treatment of pain.

Review 4. Therapeutic potential of vanilloid receptor TRPV1 agonists and antagonists as analgesics: Recent advances and setbacks.

5. Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances.

Review 6. Transient receptor potential ion channels as targets for the discovery of pain therapeutics.

7. Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin.

Review 8. The paradoxical role of the transient receptor potential vanilloid 1 receptor in inflammation.

Review 9. Clinical development of TRPV1 antagonists: targeting a pivotal point in the pain pathway.

Review 10. TRPing the switch on pain: an introduction to the chemistry and biology of capsaicin and TRPV1.

1. Short-chain phosphoinositide partitioning into plasma membrane models.

2. Understanding TRPV1 activation by ligands: Insights from the binding modes of capsaicin and resiniferatoxin.

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