N-(N',N'-dimethylglycyl)aminomethyl tert-butoxymethyl(O-methyl)phosphinate | 1239975-75-7

• 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',N'-dimethylglycyl)aminomethyl tert-butoxymethyl(O-methyl)phosphinate
• 英文别名: 2-(dimethylamino)-N-[[methoxy-[(2-methylpropan-2-yl)oxymethyl]phosphoryl]methyl]acetamide
• CAS: 1239975-75-7
• 化学式: C₁₁H₂₅N₂O₄P
• 分子量: 280.304
• InChiKey: SJUAWSWYAZZTSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(N',N'-dimethylglycyl)aminomethyl tert-butoxymethyl(O-methyl)phosphinate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 生成 C₁₀H₂₃N₂O₄P
  参考文献：
  名称：

  Computer-Aided Optimization of Phosphinic Inhibitors of Bacterial Ureases

  摘要：

  Urease inhibitors can be considered as a tool to control the damaging effect of ureolytic bacteria infections in humans which occur commonly in the developed countries. Computer-aided optimization of the aminomethylphosphinate structures by modifying both their N- and P-termini led to the invention of a novel group of inhibitors of bacterial ureases. Introduction of P-hydroxymethyl group into the molecule resulted in considerable increase of the inhibitory activity against enzymes purified from Bacillus pasteurii and Proteus vulgaris as compared with their P-methyl counterparts described previously. The designed compounds represent a competitive reversible class of urease inhibitors. The most potent, N-methyl-aminomethyl-P-hydroxymethylphosphinic acid, displayed K-i = 360 nM against P. vulgaris enzyme.

  DOI：

  10.1021/jm100340m
• 作为产物：
  描述：

  N,N-二甲基甘氨酸 、 methyl (aminomethyl)(tert-butoxymethyl)phosphinate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-(N',N'-dimethylglycyl)aminomethyl tert-butoxymethyl(O-methyl)phosphinate
  参考文献：
  名称：

  Computer-Aided Optimization of Phosphinic Inhibitors of Bacterial Ureases

  摘要：

  Urease inhibitors can be considered as a tool to control the damaging effect of ureolytic bacteria infections in humans which occur commonly in the developed countries. Computer-aided optimization of the aminomethylphosphinate structures by modifying both their N- and P-termini led to the invention of a novel group of inhibitors of bacterial ureases. Introduction of P-hydroxymethyl group into the molecule resulted in considerable increase of the inhibitory activity against enzymes purified from Bacillus pasteurii and Proteus vulgaris as compared with their P-methyl counterparts described previously. The designed compounds represent a competitive reversible class of urease inhibitors. The most potent, N-methyl-aminomethyl-P-hydroxymethylphosphinic acid, displayed K-i = 360 nM against P. vulgaris enzyme.

  DOI：

  10.1021/jm100340m

文献信息

• Computer-Aided Optimization of Phosphinic Inhibitors of Bacterial Ureases
  作者：Stamatia Vassiliou、Paulina Kosikowska、Agnieszka Grabowiecka、Athanasios Yiotakis、Paweł Kafarski、Łukasz Berlicki

  DOI：10.1021/jm100340m

  日期：2010.8.12

  Urease inhibitors can be considered as a tool to control the damaging effect of ureolytic bacteria infections in humans which occur commonly in the developed countries. Computer-aided optimization of the aminomethylphosphinate structures by modifying both their N- and P-termini led to the invention of a novel group of inhibitors of bacterial ureases. Introduction of P-hydroxymethyl group into the molecule resulted in considerable increase of the inhibitory activity against enzymes purified from Bacillus pasteurii and Proteus vulgaris as compared with their P-methyl counterparts described previously. The designed compounds represent a competitive reversible class of urease inhibitors. The most potent, N-methyl-aminomethyl-P-hydroxymethylphosphinic acid, displayed K-i = 360 nM against P. vulgaris enzyme.