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

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

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...

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Veröffentlicht in:Organic & biomolecular chemistry 2015, Vol.13 (4), p.990-994
Hauptverfasser: Wimmer, Laurin, Schönbauer, David, Pakfeifer, Peter, Schöffmann, Angela, Khom, Sophia, Hering, Steffen, Mihovilovic, Marko D.
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container_end_page 994
container_issue 4
container_start_page 990
container_title Organic & biomolecular chemistry
container_volume 13
creator Wimmer, Laurin
Schönbauer, David
Pakfeifer, Peter
Schöffmann, Angela
Khom, Sophia
Hering, Steffen
Mihovilovic, Marko D.
description 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.
doi_str_mv 10.1039/C4OB02242D
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title Developing piperine towards TRPV1 and GABA A receptor ligands – synthesis of piperine analogs via Heck-coupling of conjugated dienes
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