Referenced in: none

Automatically associated channels: Kir2.3 , TRP , TRPV , TRPV1

Title: 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, date & volume: Bioorg. Med. Chem. Lett., 2014 Jan 1 , 24, 382-5

PubMed link: http://www.ncbi.nlm.nih.gov/pubmed/24321344

Abstract
The chiral isomers of the two potent simplified RTX-based vanilloids, compounds 2 and 3, were synthesized employing highly enantioselective PTC alkylation and evaluated as hTRPV1 ligands. The analysis indicated that the R-isomer was the eutomer in binding affinity and functional activity. The agonism of compound 2R was comparable to that of RTX. Docking analysis of the chiral isomers of 3 suggested the basis for its stereospecific activity and the binding mode of 3R.