Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and their anticancer properties

被引：44

作者：

Kalla, Reddi Mohan Naidu ^{[1
]}

Choi, Jin-Seok ^{[2
,3
]}

Yoo, Jin-Wook ^{[2
]}

Byeon, Seong Jin ^{[1
]}

Heo, Min Seon ^{[1
]}

Kim, Il ^{[1
]}

机构：

[1] Pusan Natl Univ, Dept Polymer Sci & Engn, PLUS Ctr Adv Chem Technol BK21, Pusan 609735, South Korea

[2] Pusan Natl Univ, Coll Pharm, Pusan 609735, South Korea

[3] Chosun Univ, Dept Food & Drug, Kwangju 501759, South Korea

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2014年 / 76卷

基金：

新加坡国家研究基金会;

关键词：

Multicomponent reactions; One-pot synthesis; Chromenylphosphonates; Dibutylamine; Organocatalyst; Anticancer activity; ONE-POT SYNTHESIS; EFFICIENT; DERIVATIVES; CATALYST; ACID; PHOSPHONATES; TARGET;

D O I：

10.1016/j.ejmech.2014.02.025

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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.

引用

页码：61 / 66

页数：6

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