Synthesis and biological activities of α-aminophosphonates derivatives containing thieno[3,2-c]pyridine

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

Research output: Contribution to journalArticle

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1472-1477
Number of pages6
JournalChinese Journal of Organic Chemistry
Volume33
Issue number7
DOIs
Publication statusPublished - 2013 Jul 1
Externally publishedYes

Keywords

  • α-aminophosphonate
  • Synthesis
  • Thieno[3,2-c]pyridine

ASJC Scopus subject areas

  • Organic Chemistry

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