A versatile route to the synthesis of 1-substituted β-carbolines by a single step Pictet-Spengler cyclization
A versatile route to the synthesis of 1-substituted β-carbolines by a single step Pictet-Spengler cyclization
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DOI：
10.1016/j.tet.2006.08.081
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发表时间：
2006-11-20
期刊：
影响因子：
2.1
通讯作者：
Wu, Tian-Shung
中科院分区：
文献类型：
--
作者：
Yang, Mei-Lin;Kuo, Ping-Chung;Wu, Tian-Shung
A one-step conversion of L-tryptophan and activated aldehydes (1,2-dicarbonyl compounds) directly to 1-substituted beta-carbolines without formation of the tetrahydro derivatives under modified Pictet-Spengler conditions was described. Moreover, a practical application for the synthesis of a natural 1-substituted beta-carboline, luzongerine A, isolated from Illigera luzonensis was also successfully carried out utilizing this protocol. The effects of synthetic compounds 11 and 11a on nitric oxide (NO) production in LPS/IFN-gamma stimulated RAW 264.7 macrophage cells were evaluated in vitro. They displayed significant dose-dependent inhibition of inducible nitric oxide synthase (iNOS). (c) 2006 Elsevier Ltd. All rights reserved.
