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

2015, Volume 2, Issue 4

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Frontiers of Agricultural Science and Engineering >> 2015, Volume 2, Issue 4 doi: 10.15302/J-FASE-2015079

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

1. Institute of Chemical Industry of Forest Products, China Academy of Forestry; National Engineering Laboratory for Biomass Chemical Utilization; State Forestry Administration’s Key and Open Laboratory for Forest Chemical Engineering; Jiangsu Provincial Key Laboratory for Biomass Energy and Material, Nanjing 210042, China.2. Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint MI 48502, USA

Accepted: 2015-12-31 Available online: 2016-01-19

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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, H 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 IC of 23.78, 67.61 and 53.87 µmol·L , 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

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