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

doi:10.1016/j.tet.2006.08.081

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 journal › Article › peer-review

33 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 language	English
Pages (from-to)	10900-10906
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2006.08.081
Publication status	Published - 2006 Nov 20

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.08.081

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

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).",

author = "Yang, {Mei Lin} and Kuo, {Ping Chung} and Damu, {Amooru G.} and Chang, {Ren Jie} and Chiou, {Wen Fei} and Wu, {Tian Shung}",

note = "Funding Information: The authors are thankful to the National Science Council, Taiwan, ROC (NSC 92-2113-M-006-011) for financial support of the present research. ",

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AU - Yang, Mei Lin

AU - Kuo, Ping Chung

AU - Damu, Amooru G.

AU - Chang, Ren Jie

AU - Chiou, Wen Fei

AU - Wu, Tian Shung

N1 - Funding Information: The authors are thankful to the National Science Council, Taiwan, ROC (NSC 92-2113-M-006-011) for financial support of the present research.

PY - 2006/11/20

Y1 - 2006/11/20

N2 - 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).

AB - 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).

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

Abstract

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