N-(N'-benzyloxycarbonylglycyl)aminomethyl(P-methyl)phosphinothioic acid | 1056902-34-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(N'-benzyloxycarbonylglycyl)aminomethyl(P-methyl)phosphinothioic acid
• 英文别名: [(2-{[(Benzyloxy)carbonyl]amino}acetamido)methyl](methyl)sulfanylidenephosphinous acid；benzyl N-[2-[[hydroxy(methyl)phosphinothioyl]methylamino]-2-oxoethyl]carbamate
• CAS: 1056902-34-1
• 化学式: C₁₂H₁₇N₂O₄PS
• 分子量: 316.318
• InChiKey: VKQPGHNXUFJXTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  O-methyl N-(N-benzyloxycarbonylglycyl)aminomethyl(P-methyl)phosphinothioate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 以77%的产率得到N-(N'-benzyloxycarbonylglycyl)aminomethyl(P-methyl)phosphinothioic acid
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel Organophosphorus Inhibitors of Bacterial Ureases

  摘要：

  A new group of organophosphorus inhibitors of urease, P-methyl phosphinic acids was discovered by using the structure based inhibitor design approach. Several derivatives of the lead compound, aminomethyl(P-methyl)phosphinic acid, were synthesized successfully. Their potency was evaluated in vitro against urease from Bacillus pasteurii and Proteus vulgaris. The studied compounds constitute a group of competitive, reversible inhibitors of bacterial ureases. Obtained thiophosphinic analogues of the most effective structures exhibited kinetic characteristics of potent, slow binding urease inhibitors, with K-i = 170 nM (against B. pasteurii enzyme) for the most active N-(N'-benzyloxycarbonylglycyl)aminomethyl(P-methyl)phosphinothioic acid.

  DOI：

  10.1021/jm800570q