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

被引：14
作者：
Wimmer, Laurin [1 ]
Schoenbauer, David [1 ]
Pakfeifer, Peter [2 ]
Schoeffmann, Angela [2 ]
Khom, Sophia [2 ]
Hering, Steffen [2 ]
Mihovilovic, Marko D. [1 ]
机构：
[1] Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria
[2] Univ Vienna, Dept Pharmacol & Toxicol, A-1090 Vienna, Austria
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 04期
基金：
奥地利科学基金会;
关键词：
PALLADIUM-CATALYZED ARYLATION; STEREOSELECTIVE-SYNTHESIS; A RECEPTORS; 1,3-DIENES; ARYL; VINYLATION; ESTERS;
D O I：
10.1039/c4ob02242d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Piperine, the pungent alkaloid of black pepper, and several of its derivatives are modulators of gamma-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.
引用
收藏
页码：990 / 994
页数：5
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