diphenyl 1-(4-chlorophenylamino)-1-(pyridin-3-yl)ethylphosphonate | 1366561-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diphenyl 1-(4-chlorophenylamino)-1-(pyridin-3-yl)ethylphosphonate
• 英文别名: 4-chloro-N-(1-diphenoxyphosphoryl-1-pyridin-3-ylethyl)aniline
• CAS: 1366561-34-3
• 化学式: C₂₅H₂₂ClN₂O₃P
• 分子量: 464.888
• InChiKey: SZFOUKUNTHCRFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-乙酰基吡啶 、 亚磷酸三苯酯 、 对氯苯胺 在 lithium perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以81%的产率得到diphenyl 1-(4-chlorophenylamino)-1-(pyridin-3-yl)ethylphosphonate
  参考文献：
  名称：

  Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates

  摘要：

  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, H-1 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 Candida albicans and Saccharomyces cerevisiae as fungi, at low concentrations (10-100 mu g/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. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.015

文献信息

• Synthesis, antimicrobial and anticancer activities of a novel series of diphenyl 1-(pyridin-3-yl)ethylphosphonates
  作者：Mohamed F. Abdel-Megeed、Badr E. Badr、Mohamed M. Azaam、Gamal A. El-Hiti

  DOI：10.1016/j.bmc.2012.02.015

  日期：2012.4

  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, H-1 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 Candida albicans and Saccharomyces cerevisiae as fungi, at low concentrations (10-100 mu g/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. (C) 2012 Elsevier Ltd. All rights reserved.