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

Laurin Wimmer; David Schönbauer; Peter Pakfeifer; Angela Schöffmann; Sophia Khom; Steffen Hering; Marko D. Mihovilovic

doi:10.1039/C4OB02242D

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Developing piperine towards TRPV1 and GABA_A receptor ligands – synthesis of piperine analogs via Heck-coupling of conjugated dienes†

Laurin Wimmer,^a David Schönbauer,^a Peter Pakfeifer,^b Angela Schöffmann,^b Sophia Khom,^b Steffen Hering^b and Marko D. Mihovilovic*^a

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* Corresponding authors

^a Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, 1060 Vienna, Austria
E-mail: marko.mihovilovic@tuwien.ac.at
Fax: +43 1 58801 154 99
Tel: +43 1 58801 163615

^b Department of Pharmacology and Toxicology, University of Vienna, Althanstr. 14, 1090 Vienna, Austria

Abstract

Piperine, the pungent alkaloid of black pepper, and several of its derivatives are modulators of γ-amino butyric acid type A (GABA_A) 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 GABA_A or the TRPV1 receptor.

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Article information

DOI: https://doi.org/10.1039/C4OB02242D
Article type: Communication
Submitted: 22 Oct 2014
Accepted: 10 Nov 2014
First published: 01 Dec 2014

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Org. Biomol. Chem., 2015,13, 990-994

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Developing piperine towards TRPV1 and GABA_A receptor ligands – synthesis of piperine analogs via Heck-coupling of conjugated dienes

L. Wimmer, D. Schönbauer, P. Pakfeifer, A. Schöffmann, S. Khom, S. Hering and M. D. Mihovilovic, Org. Biomol. Chem., 2015, 13, 990 DOI: 10.1039/C4OB02242D

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Organic & Biomolecular Chemistry