Department of Chemistry, Faculty of Science, Tanta University, Tanta 31527, Egypt.
Bioorg Med Chem. 2012 Apr 1;20(7):2252-8. doi: 10.1016/j.bmc.2012.02.015. Epub 2012 Feb 13.
A novel series of diphenyl 1-(arylamino)-1-(pyridin-3-yl)ethylphosphonates 1-5 was obtained in high yields from reactions of 3-acetyl pyridine with aromatic amines and triphenylphosphite in the presence of lithium perchlorate as a catalyst. The structures of the synthesized compounds were confirmed by IR, (1)H NMR spectral data and microanalyses. Compounds 1-5 showed high antimicrobial activities against Escherichia coli (NCIM2065) as a Gram-negative bacterium, Bacillus subtilis (PC1219) and Staphylococcus aureus (ATCC25292) as Gram-positive bacteria and Candidaalbicans and Saccharomyces cerevisiae as fungi, at low concentrations (10-100 μg/mL). Also, the synthesized compounds showed significant cytotoxicity anticancer activities against liver carcinoma cell line (HepG2) and human breast adenocarcinoma cell line (MCF7). The lethal dose of the synthesized compounds was also determined and indicated that most compounds are safe to use.
从 3-乙酰基吡啶与芳香胺和三苯基膦在高氯酸锂作为催化剂的存在下反应，得到了一系列新型的二苯基 1-(芳氨基)-1-(吡啶-3-基)乙基膦酸酯 1-5，产率很高。通过红外光谱、（1）H NMR 谱数据和微量分析确认了所合成化合物的结构。化合物 1-5 在低浓度（10-100μg/mL）下对革兰氏阴性菌大肠杆菌（NCIM2065）、革兰氏阳性菌枯草芽孢杆菌（PC1219）和金黄色葡萄球菌（ATCC25292）以及真菌白色念珠菌和酿酒酵母表现出很高的抗菌活性。此外，所合成的化合物对肝癌细胞系（HepG2）和人乳腺癌腺癌细胞系（MCF7）也表现出显著的细胞毒性抗癌活性。还确定了合成化合物的致死剂量，表明大多数化合物使用安全。
