Synthesis and Biological Activities of α-Aminophosphonates Derivatives Containing Thieno[3,2-c]pyridine

doi:10.6023/cjoc201301045

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1472-1477.DOI: 10.6023/cjoc201301045 Previous Articles Next Articles

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含噻吩并[3,2-c]吡啶α-氨基膦酸酯类衍生物的合成及生物活性的研究

马姣丽^a, 朱文娟^a, 李静^a, 纪朋^b, 朱智志^b, 廖新成^a

a 郑州大学化学与分子工程学院郑州 450052;
b 河南中烟工业有限责任公司郑州 450016

收稿日期:2013-01-19 修回日期:2013-03-05 发布日期:2013-03-14
通讯作者: 廖新成 E-mail:lxc66@zzu.edu.cn;xiaojiaoli1986@163.com
基金资助:
国家自然科学基金(No. 21171149)资助项目.

Synthesis and Biological Activities of α-Aminophosphonates Derivatives Containing Thieno[3,2-c]pyridine

Ma Jiaoli^a, Zhu Wenjuan^a, Li Jing^a, Ji Peng^b, Zhu Zhizhi^b, Liao Xincheng^a

a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052;
b Henan Tobacco Industry Co., LTD., Zhengzhou 450016

Received:2013-01-19 Revised:2013-03-05 Published:2013-03-14
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21171149).

A series of novel α-aminophosphonate derivatives containing thieno[3,2-c]pyridine (6a～6p), which have never been reported in literature, were synthesized from thieno[3,2-c]pyridine-2-carbaldehyde, phosphate ester and aromatic amine by the Mannich-type reaction. Thieno[3,2-c]pyridine-2-carbaldehyde (4) was produced via nucleophilic addition reaction, reduction, substitution reaction, cyclization, formylation using 3-thiophene formaldehyde and 2,2-dimethoxyethanamine as the starting material. The structures of all compounds have been confirmed by ¹H NMR, ¹³C NMR, ³¹P NMR, IR and MS techniques. The preliminary results of biological tests indicated that most of the title compounds exhibit relatively good anticancer activity against EC109, HepG2 at the concentration of 50 μg/mL, especially compounds 6k and 6o have more than 90% inhibitory rate against HepG2

Key words: α-aminophosphonate, thieno[3,2-c]pyridine, synthesis

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Ma Jiaoli, Zhu Wenjuan, Li Jing, Ji Peng, Zhu Zhizhi, Liao Xincheng. Synthesis and Biological Activities of α-Aminophosphonates Derivatives Containing Thieno[3,2-c]pyridine[J]. Chin. J. Org. Chem., 2013, 33(07): 1472-1477.

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含噻吩并[3,2-c]吡啶α-氨基膦酸酯类衍生物的合成及生物活性的研究

Synthesis and Biological Activities of α-Aminophosphonates Derivatives Containing Thieno[3,2-c]pyridine

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