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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1472 - 1477

DOI: https://doi.org/10.6023/cjoc201301045

Articles

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

  • Ma Jiaoli ,
  • Zhu Wenjuan ,
  • Li Jing ,
  • Ji Peng ,
  • Zhu Zhizhi ,
  • Liao Xincheng
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  • a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052;
    b Henan Tobacco Industry Co., LTD., Zhengzhou 450016

Received date: 2013-01-19

  Revised date: 2013-03-05

  Online published: 2013-03-14

Supported by

Project supported by the National Natural Science Foundation of China (No. 21171149).

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Abstract

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

Cite this article

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]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1472 -1477 . DOI: 10.6023/cjoc201301045

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