Chinese Journal of Organic Chemistry >
Study on the Synthesis of Benzophenanthridine Analogues via the Cyclization Reaction of Aryl-enamine Ester and Their Cytotoxicity
Received date: 2018-11-04
Revised date: 2019-01-18
Online published: 2019-04-08
Supported by
Project supported by the National Natural Science Foundation of China (No. 21462008), the Natural Science Foundation of Guangxi Province (Nos. 2015GXNSFDA139009, 2017GXNSFDA198045), and the Ministry of Education of China (No. IRT_16R15).
Study on the synthesis and bioactivity of benzophenanthridine alkaloids or its analogues had been the interests of many reserach groups who dedicated to organic synthsis or medicinal chemistry, due to their broad spectrum of biological activities such as antitumor, antiviral, antiinflammatory, antibacterial and so on. In this paper, twenty three novel analogue of benzophenanthridines were synthesized starting from isochroman-3-one and aromatic amines in 3~4 steps via the cyclization reaction of aryl-enamine ester as the key transformation. The structures of the targeted compounds were characterized and comfirmed by 1H NMR, 13C NMR and HRMS. In vitro cytotoxic activity against a panel of human tumor cell lines (MGC-803, HepG2, NCI-H460, SKOV3, T-24) and nomal cell HL-7702 was also evaluated via methyl thiazolyl tetrazolium (MTT) assay. The result indicated that only a very few of the targeted compounds exhibted moderate cytotoxic activity against the tested cell lines. Among them 2,3-dimethoxy-isochrysen[4,3-c]quinoline (4j) and 2-chloro-isochromone[4,3-c]quinoline (5f) displayed moderate antiproliferative activity against human tumor cell lines on T-24 and NCI-H460 with IC50 values of 15.8 and 16.7 μmol/L, respectively.
Wang Zengbo , Tian Cheng , Liu Qingqing , Zhang Wei , Pan Chengxue , Su Guifa . Study on the Synthesis of Benzophenanthridine Analogues via the Cyclization Reaction of Aryl-enamine Ester and Their Cytotoxicity[J]. Chinese Journal of Organic Chemistry, 2019 , 39(7) : 1962 -1969 . DOI: 10.6023/cjoc201811004
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