A versatile route to the synthesis of 1-substituted β-carbolines by a single step Pictet-Spengler cyclization

Mei Lin Yang, Ping Chung Kuo, Amooru G. Damu, Ren Jie Chang, Wen Fei Chiou, Tian Shung Wu

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

A one-step conversion of l-tryptophan and activated aldehydes (1,2-dicarbonyl compounds) directly to 1-substituted β-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 β-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-γ stimulated RAW 264.7 macrophage cells were evaluated in vitro. They displayed significant dose-dependent inhibition of inducible nitric oxide synthase (iNOS).

Original languageEnglish
Pages (from-to)10900-10906
Number of pages7
JournalTetrahedron
Volume62
Issue number47
DOIs
Publication statusPublished - 2006 Nov 20

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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