Synthetic studies of neoclerodane diterpenes from Salvia divinorum:: Selective modification of the furan ring

被引：39

作者：

Harding, Wayne W.

Schmidt, Matthew

Tidgewell, Kevin

Kannan, Pavitra

Holden, Kenneth G.

Dersch, Christina M.

Rothman, Richard B.

Prisinzano, Thomas E. ^{[1
]}

机构：

[1] Univ Iowa, Coll Pharm, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA

[2] Holden Labs, Carmel, CA 93923 USA

[3] NIDA, Clin Psychopharmacol Sect, IRP, NIH,DHHS, Baltimore, MD 21224 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2006年 / 16卷 / 12期

关键词：

salvinorin A; kappa; opioid; Salvia divinorum; heterocycle;

D O I：

10.1016/j.bmcl.2006.03.062

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A synthetic sequence has been developed to selectively functionalize the furan ring of the natural product salvinorin A (2a). The synthetic routes described convert the furan ring in 2a into an N-sulfonylpyrrole, oxazole or an oxadiazole. In addition, a procedure has been found to remove the furan skeleton completely. Biological results indicate that replacement of the furan ring with an N-sulfonylpyrrole leads to reduced affinity and efficacy at K opioid receptors. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：3170 / 3174

页数：5

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