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

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

Publications: Contribution to journal › Article › Peer Reviewed

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.

Original language	English
Pages (from-to)	990-994
Number of pages	5
Journal	Organic & Biomolecular Chemistry
Volume	13
Issue number	4
DOIs	https://doi.org/10.1039/c4ob02242d
Publication status	Published - 28 Jan 2015

Austrian Fields of Science 2012

301207 Pharmaceutical chemistry
301206 Pharmacology

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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.",

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T1 - Developing piperine towards TRPV1 and GABAA receptor ligands - synthesis of piperine analogs via Heck-coupling of conjugated dienes

AU - Wimmer, Laurin

AU - Schönbauer, David

AU - Pakfeifer, Peter

AU - Schöffmann, Angela

AU - Khom, Sophia

AU - Hering, Steffen

AU - Mihovilovic, Marko D

PY - 2015/1/28

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N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84937427432

U2 - 10.1039/c4ob02242d

DO - 10.1039/c4ob02242d

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JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 4

ER -

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

Abstract

Austrian Fields of Science 2012

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