N,N-dimethyl-(P-aminomethyl)(P-hydroxymethyl)phosphinic | 1239975-64-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-(P-aminomethyl)(P-hydroxymethyl)phosphinic
• 英文别名: (Dimethylamino)Methyl(Hydroxymethyl)Phosphinic Acid；(dimethylamino)methyl-(hydroxymethyl)phosphinic acid
• CAS: 1239975-64-4
• 化学式: C₄H₁₂NO₃P
• 分子量: 153.118
• InChiKey: HDEKDPVRCOGVAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 hydroxymethylphosphinic acid 、 二甲胺 在 盐酸 、 phosphinic acid 作用下， 以 乙醇 、 水 为溶剂， 反应 53.0h， 以52%的产率得到N,N-dimethyl-(P-aminomethyl)(P-hydroxymethyl)phosphinic
  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

• Bis(aminomethyl)phosphinic Acid, a Highly Promising Scaffold for the Development of Bacterial Urease Inhibitors
  作者：Katarzyna Macegoniuk、Anna Dziełak、Artur Mucha、Łukasz Berlicki

  DOI：10.1021/ml500380f

  日期：2015.2.12

  Inhibitors of bacterial ureases are considered to be promising compounds in the treatment of infections caused by Helicobacter pylori in the gastric tract and/or by urealytic bacteria (e.g., Proteus species) in the urinary tract. A new, extended transition state scaffold, bis(aminomethyl)phosphinic acid, was successfully explored for the construction of effective enzyme inhibitors. A reliable methodology

  细菌脲酶的抑制剂被认为是治疗由胃道中的幽门螺杆菌和/或由尿道中的尿素分解细菌（例如变形杆菌属）引起的感染的有前途的化合物。一个新的扩展的过渡态支架，双（氨基甲基）次膦酸，成功地探索了有效的酶抑制剂的建设。阐述了在三组分曼尼希型反应中合成次膦酸酯类似物的可靠方法。对获得的分子进行了针对从巴氏孢子虫和米氏变形杆菌纯化的脲酶的测定，发现氨基甲基（Nn-己基氨基甲基）次膦酸是最有效的抑制剂，其Ki = 108 nM。
• 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.