期刊
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
卷 76, 期 -, 页码 61-66出版社
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2014.02.025
关键词
Multicomponent reactions; One-pot synthesis; Chromenylphosphonates; Dibutylamine; Organocatalyst; Anticancer activity
资金
- Basic Science Research Program through the National Research Foundation of Korea - Ministry of Education [2012R1A1A2041315]
- Fusion Research Program for Green Technologies through the National Research Foundation of Korea - Ministry of Education [2012M3C1A1054502]
- BK21 PLUS Program
A series of 2-amino-3-cyano-4H-chromen-4-ylphosphonates have been synthesized by reacting substituted salicylaldehydes, malononitrile, and dialkylphosphites using a catalytic amount of dibutylamine as an organocatalyst employing Knoevenagel, Pinner, and phospha-Michael reactions simultaneously in ethanol. This protocol is an environmentally friendly procedure and gives high yields of the desired compounds (85-96%). In addition, no extraction or chromatography steps are needed to obtain the desired products. The compounds are tested against the viability of adenocarcinomic human alveolar basal epithelial (A549) and human epidermoid cancer (KB) cell lines using an MU assay. Among these, diethyl 2-amino-3-cyano-4H-chromen-4-ylphosphonate and diethyl 2-amino-6-bromo-3-cyano-4H-chromen-4-ylphosphonate showed promising anticancer activity against the two tested cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.
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