Referenced in: none

Automatically associated channels: TRP , TRPV , TRPV1

Title: Developing piperine towards TRPV1 and GABAA receptor ligands--synthesis of piperine analogs via Heck-coupling of conjugated dienes.

Authors: Laurin Wimmer, David Schönbauer, Peter Pakfeifer, Angela Schöffmann, Sophia Khom, Steffen Hering, Marko D Mihovilovic

Journal, date & volume: Org. Biomol. Chem., 2015 Jan 28 , 13, 990-4

PubMed link: http://www.ncbi.nlm.nih.gov/pubmed/25438036

Abstract
Piperine, the pungent alkaloid of black pepper, and several of its derivatives are modulators of γ-amino butyric acid type A (GABAA) receptors. Concomitantly, this natural product has also been reported to activate transient receptor potential vanilloid type 1 (TRPV1) receptors. We have developed a Heck cross-coupling reaction of conjugated dienamides enabling the rapid assembly of piperine derivatives containing a modified aromatic core. Upon assessment of a focussed compound library, key aromatic substituents were identified selectively affecting either the GABAA or the TRPV1 receptor.