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



马姣丽a, 朱文娟a, 李静a, 纪朋b, 朱智志b, 廖新成a   

  1. 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;
  • 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 Jiaolia, Zhu Wenjuana, Li Jinga, Ji Pengb, Zhu Zhizhib, Liao Xinchenga   

  1. 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 (6a6p), 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