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Synthesis and Biological Evaluation of Heterocyclic Substituted Bis(indolyl)methanes

[ Vol. 17 , Issue. 2 ]

Author(s):

Min-Xin Li, Xiao-Jia Pu, Xia Zhang, Xi Zheng, Hui Gao, Wei-Lie Xiao, Chun-Ping Wan* and Ze-Wei Mao*   Pages 144 - 150 ( 7 )

Abstract:


Background: Bis(indolyl)methane derivatives are widely found in nature with a broad range of biological and pharmacological activities. The development of techniques for the synthesis and functionalization of bis(indolyl)methanes have attracted more and more attention in recent years.

Objective: To study the synthesis and biological activity of heterocyclic substituted bis(indolyl)methanes.

Materials and Methods: A series of heterocyclic substituted bis(indolyl)methanes (3a-3p) have been prepared by condensation reaction of indole and heterocyclic aldehydes catalyzed by boron trifluoride etherate with high yields. Preliminary in vitro anti-inflammatory in lipopolysaccharide (LPS)-stimulated RAW-264.7 macrophages and cytotoxic activity against human tumor cell lines (A549, Hela and SGC7901) by MTT assay were tested.

Results: The result indicated that heterocyclic substituted bis(indolyl)methanes showed good antiinflammatory and selective cytotoxic activity. Especially, compounds 3o, 3p and 3q displayed similar inhibitory effect on the generation of NO to positive control dexamethasone, and compound 3q displayed similar selective cytotoxic activity to 5-FU.

Conclusion: Heterocyclic substituted bis(indolyl)methanes may be used as potential anti-inflammatory and anticancer leads.

Keywords:

Synthesis, bis(indolyl)methanes, anti-inflammatory activity, cytotoxic activity, heterocyclic, anticancer leads.

Affiliation:

College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500, College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500, College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500, Central Laboratory, The NO.1 Affiliated Hospital of Yunnan University of Chinese Medicine, Kunming 650021, College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education and Yunnan Province, School of Chemical Science and Technology, Yunnan University, Kunming 650091, Central Laboratory, The NO.1 Affiliated Hospital of Yunnan University of Chinese Medicine, Kunming 650021, College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500

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