Chinese Journal of Organic Chemistry >
Synthesis, Crystal Structure and Antitumor Activity of Novel 5-Chloro-β-carboline Derivatives
Received date: 2020-06-15
Revised date: 2020-08-06
Online published: 2020-08-27
Supported by
the Scientific Research Innovation Project in Shihezi University(SHYL-YB201804); the Program for Changjiang Scholars and Innovative Research Team in University(IRT15R46); the Yangtze River Scholar Research Project of Shihezi University(CJXZ201601)
Sixteen novel 5-chloro- β-carboline derivatives were synthesized from harmane in four steps: N 9-alkylation, nitration, reduction, and Borch reduction. The structures of target compounds were confirmed by 1H NMR, 13C NMR, and HRMS. A single crystal of 5-chloro-1,9-dimethyl- N-(pyridin-3-ylmethyl)- β-carboline (5e) was cultured, and its single crystal structure was determined by X-ray diffraction study. The in vitro antiproliferative activities were evaluated in a panel of cancer cell lines (A549, BGC-823, CT-26, Bel-7402, and MCF-7) via methyl thiazolyl tetrazolium (MTT) assay. The results indicated that some compounds had good activities, and especially N-(2,6-difluorobenzyl)-1-methyl-5-chloro-9-(2,3,4,5,6-pentafluorobenzyl)- β- carboline-6-amine (5j) and N-(pyridin-3-ylmethyl)-1-methyl-5-chloro-9-(2,3,4,5,6-pentafluorobenzyl)- β-carboline-6-amine (5m) showed considerable antitumor activity with IC50 values lower than 10 μmol•L –1 against four cancer cell lines.
Yue Sun , Liang Guo , Wenxi Fan , Wei Chen , Jie Zhang , Bin Dai . Synthesis, Crystal Structure and Antitumor Activity of Novel 5-Chloro-β-carboline Derivatives[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 400 -406 . DOI: 10.6023/cjoc202006026
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