Synthesis and anticancer activity of (+)-nopinone-based 2-amino-3-cyanopyridines

Abstract

Twelve (+)-nopinone-based 2-amino-3-cyanopyridines 4a—l were synthesized from (—)-β-pinene. The structures of these compounds were characterized by FT-IR, 1H NMR, and ESI-MS. All the compounds were tested for their anticancer activity against lung cancer cell line A549, gastric cancer cell line MKN45 and breast cancer cell line MCF7 by MTT method, respectively. The results showed that compounds 4f, 4j and 4k had promising anticancer activity against these cancer cell lines, in particular, compound 4f exhibited broad-spectrum and highly efficient anticancer activity against cell lines A549, MKN45 and MCF7 with IC50 of 23.78, 67.61 and 53.87 μmol·L-1, respectively. The preliminary analysis of the structure activity relationship implied that the Br or Cl substituted group of the benzene ring in these derivatives significantly contributed to the anticancer activity.

Keywords

• b-pinene|nopinone|synthesis|2-amino-3-cyanopyridine|anticancer