<2-(pyridinio)-1-phosphoryl>ethylphosphonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: <2-(pyridinio)-1-phosphoryl>ethylphosphonate
• 英文别名: [2-(pyridinio)-1-phosphoryl]ethylphosphonate；Bisphosphonate, 60；hydroxy-(1-phosphono-2-pyridin-1-ium-1-ylethyl)phosphinate
• 化学式: C₇H₁₁NO₆P₂
• 分子量: 267.115
• InChiKey: QNDFCGRVKQTFAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吡啶 、 vinylidene-1,1-diphosphonic acid 以 水 为溶剂， 反应 2.0h， 以85%的产率得到<2-(pyridinio)-1-phosphoryl>ethylphosphonate
  参考文献：
  名称：

  Activity of Nitrogen-Containing and Non-Nitrogen-Containing Bisphosphonates on Tumor Cell Lines

  摘要：

  We synthesized and tested three series of bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines: MCF-7 (breast), NCI-H460 (lung), and SF-268 (CNS). The first series of compounds consisted of 49 nitrogen-containing bisphosphonates, the most active species being a tetrakispivaloyloxymethyl (POM) ester, having an (average) IC50 of 6.8 mu M. The second series of compounds consisted of nine terphenylbisphosphonates, the most active species also being a POM ester, having an IC50 of 2.2 mu M. The third series of compounds consisted of seven halogen or cyanophenylbisphosphonates, the most active species again being a POM ester, having an IC50 of 500 nM. Taken together, these results are of interest because they show that bisphosphonate esters can have potent activity against a variety of tumor cell lines, with the most active terphenyl-and halophenyl-containing species having IC50 values similar to 10-40x lower than the most potent commercially available bisphosphonates.

  DOI：

  10.1021/jm060280e

文献信息

• Reactions of vinylidenediphosphonic acid with nucleophiles
  作者：I. S. Alfer'ev、N. V. Mikhalin

  DOI：10.1007/bf00714446

  日期：1995.8

  It has been shown that heterocyclic amines can be added to the activated double bond of vinylidenediphosphonic acid to form adducts with betaine structures. Of aliphatic amines only trimethylamine reacts with vinylidenediphosphonic acid.

  已经表明杂环胺可以加到亚乙烯基二膦酸的活化双键上以形成具有甜菜碱结构的加合物。在脂肪胺中，只有三甲胺与亚乙烯基二膦酸反应。