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Re-engineering and Synthesis of Cytotoxic 2,3:7,8-di(alkylenedioxy)-extended Analogs of Quaternary Sanguinarine Chloride

Re-engineering and Synthesis of Cytotoxic 2,3:7,8-di(alkylenedioxy)-extended Analogs of Quaternary Sanguinarine Chloride

Qi-Lin Li, An-Jun Deng, Ming Ji, Zhi-Hong Li, Xiao-Guang Chen, Hai-Lin Qin

J Asian Nat Prod Res. 2018 Dec;20(12):1137-1153.

PMID: 30415574

Abstract:

A method was developed to synthesize 2,3:7,8-di(alkylenedioxy)-extended analogs of quaternary sanguinarine chloride. 1-Bromo-2-bromomethyl-3,4-alkylenedioxy benzenes and 6,7-alkylenedioxynaphthalen-1-amines were synthesized first. Reactions to construct the target compounds with these two series of synthons involved alterations on a published method for synthesizing 2,3,7,8-tetraoxygenated derivatives of benzo[c]phenanthridinium, substituting benzyl bromides for benzoic aldehydes, prolonging the radical annulation time, and conducting N-methylation with formic acid and NaBH4. All the target compounds showed the same or better in vitro growth inhibitory activities against cancer cell lines compared with the positive compound. The structure activity relationship relevant to cytotoxicity and lipophilicity of the target compounds was produced.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP5578734	Sanguinarine chloride		5578-73-4	Price

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