methyl N-benzyloxycarbonylaminomethylphosphinate | 107148-17-4

• 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: methyl N-benzyloxycarbonylaminomethylphosphinate
• CAS: 107148-17-4
• 化学式: C₁₀H₁₄NO₄P
• 分子量: 243.199
• InChiKey: XBZVYASUNMBRKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl N-benzyloxycarbonylaminomethylphosphinate 在 N-甲基吗啉 、 盐酸 、 sodium hydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11

  摘要：

  We have synthesized a series of phosphinic acids as inhibitors of a metalloprotease endothelin converting enzyme (ECE). Potent ECE inhibitors 4g and 4o were identified. These compounds are members of a novel class of ECE inhibitors that are also potent inhibitors of angiotensin converting enzyme and neutral endopeptidase. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00297-1
• 作为产物：
  描述：

  N-benzyloxycarbonylaminomethyl-H-phosphinic acid 、 三甲基硅烷化重氮甲烷 在 溶剂黄146 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 以82%的产率得到methyl N-benzyloxycarbonylaminomethylphosphinate
  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

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.