普乌佩烯酮的化学性质：对其醌甲基化物体系的1,6-共轭加成反应。

Chemistry of puupehenone: 1,6-conjugate addition to its quinone-methide system.

作者信息

Zjawiony J K, Bartyzel P, Hamann M T

机构信息

Department of Pharmacognosy, National Center for the Development of Natural Products, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi 38677,

出版信息

J Nat Prod. 1998 Dec;61(12):1502-8. doi: 10.1021/np9802062.

DOI:10.1021/np9802062

PMID:9868151

Abstract

The marine natural product puupehenone (1), isolated in good yields from sponges of the genus Hyrtios, has been shown to undergo stereospecific 1,6-conjugate addition to its quinone-methide system. Several nucleophilic agents such as hydrogen cyanide, Grignard reagents, and nitroalkanes were studied, producing structurally diverse compounds. This lead optimization study was initiated due to the bioactivity of puupehenone and its natural analogues, which includes numerous previous reports of potential anticancer and antiinfective activity.

摘要

从Hyrtios属海绵中以高产率分离得到的海洋天然产物puupehenone（1），已被证明可对其醌甲基化物体系进行立体定向的1,6-共轭加成。研究了几种亲核试剂，如氰化氢、格氏试剂和硝基烷烃，得到了结构多样的化合物。由于puupehenone及其天然类似物具有生物活性，包括此前众多关于其潜在抗癌和抗感染活性的报道，因此启动了这项先导化合物优化研究。