N-methylaminomethyl(P-methyl)phosphinic acid | 91585-48-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methylaminomethyl(P-methyl)phosphinic acid
• 英文别名: N-methylaminomethyl-methylphosphonic acid；Methyl-[(methylazaniumyl)methyl]phosphinate
• CAS: 91585-48-7
• 化学式: C₃H₁₀NO₂P
• mdl: MFCD01332234
• 分子量: 123.092
• InChiKey: NKKBRHFRJZUQDL-UHFFFAOYSA-N

物化性质

• 沸点：
  336.0±25.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-methylaminomethyl(P-methyl)phosphinic acid 在 盐酸 、 亚磷酸 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Tyka, Roman; Haegele, Gerhard; Peters, Juergen, Phosphorus and Sulfur and the Related Elements, 1987, vol. 34, p. 31 - 38

  摘要：

  DOI：
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 N-methylaminomethyl(P-methyl)phosphinic 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

文献信息

• N-substituted aminomethanephosphonic and aminomethane-P-methylphosphinic acids as inhibitors of ureases
  作者：Łukasz Berlicki、Marta Bochno、Agnieszka Grabowiecka、Arkadiusz Białas、Paulina Kosikowska、Paweł Kafarski

  DOI：10.1007/s00726-011-0920-4

  日期：2012.5

  inhibitor design approach using available crystal structures of bacterial urease, N-substituted derivatives of aminomethylphosphonic and P-methyl-aminomethylphosphinic acids were designed and synthesized. In inhibition studies using urease from Bacillus pasteurii and Canavalia ensiformis, the N,N-dimethyl derivatives of both lead structures were most effective with dissociation constants in the low micromolar

  基于具有共价碳磷键的二酰氨基磷酸盐结构的未扩展小分子被开发为一组新的抑制剂，以控制微生物尿素分解。应用基于结构的抑制剂设计方法，利用细菌脲酶的可用晶体结构，设计并合成了氨基甲基膦酸和P-甲基-氨基甲基次膦酸的N-取代衍生物。在使用来自巴氏杆菌和Canavalia ensiformis 的脲酶的抑制研究中，两种先导结构的N , N -二甲基衍生物在低微摩尔范围内的解离常数 ( K i ) 下最有效。  = 13 ± 0.8 和 0.62 ± 0.09 μM，分别）。上的尿素分解菌株全细胞研究奇异变形杆菌表现出的高效率N，N-二甲基和aminomethane- N-甲基衍生物P -methylphosphinic酸用于病原性细菌的尿素酶的抑制作用。使用 NMR 技术在 30 天内证实了所选抑制剂的高水解稳定性。
• Maier, Ludwig, Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 62, # 1.4, p. 29 - 34
  作者：Maier, Ludwig

  DOI：——

  日期：——
• A Convenient Synthesis of<i>N</i>-Alkylaminomethanephosphonic and<i>N</i>-Alkylaminomethylphosphinic Acids
  作者：Roman Tyka、Gerhard Hägele

  DOI：10.1055/s-1984-30776

  日期：——
• TYKA, R.;HAEGELE, G., SYNTHESIS, BRD, 1984, N 3, 218-219
  作者：TYKA, R.、HAEGELE, G.

  DOI：——

  日期：——
• Design, Synthesis, and Evaluation of Novel Organophosphorus Inhibitors of Bacterial Ureases
  作者：Stamatia Vassiliou、Agnieszka Grabowiecka、Paulina Kosikowska、Athanasios Yiotakis、Paweł Kafarski、Łukasz Berlicki

  DOI：10.1021/jm800570q

  日期：2008.9.25

  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.