N-butyl-1-aminomethane-1,1-diphosphonic acid | 67242-29-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: N-butyl-1-aminomethane-1,1-diphosphonic acid
• 英文别名: 1-Ammonio-1-phosphonopentane-1-phosphonic acid；[(1R)-1-azaniumyl-1-phosphonopentyl]-hydroxyphosphinate
• CAS: 67242-29-9
• 化学式: C₅H₁₅NO₆P₂
• 分子量: 247.125
• InChiKey: XTMZDPMXSRLXCC-UHFFFAOYSA-N

物化性质

• 熔点：
  245-247 °C(Solv: hydrochloric acid (7647-01-0); ethanol (64-17-5))
• 沸点：
  516.9±60.0 °C(Predicted)
• 密度：
  1.613±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  141
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  戊腈 在 亚磷酸 、 苯磺酸 、 三氯化磷 作用下， 反应 16.17h， 以25%的产率得到N-butyl-1-aminomethane-1,1-diphosphonic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-amino-1,1-bisphosphonates derived from fatty acids against Trypanosoma cruzi targeting farnesyl pyrophosphate synthase

  摘要：

  We have investigated the effect of a series of 1-amino-1,1-bisphosphonates derived from fatty acids against proliferation of the clinically more relevant form of Trypanosoma cruzi, the causative agent of American trypanosomiasis (Chagas' disease). Some of these drugs were potent inhibitors against the intracellular form of the parasite, exhibiting IC50 values at low micromolar level. Cellular activity was associated with the inhibition of enzymatic activity of T cruzi farnesyl pyrophosphate synthase. As bisphosphonate-containing drugs are FDA-approved for the treatment of bone resorption disorders, their potential innocuousness makes them good candidates to control tropical diseases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.060

文献信息

• Schuelke, Ulrich, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 51/52, p. 623 - 626
  作者：Schuelke, Ulrich

  DOI：——

  日期：——
• Synthesis and biological evaluation of 1-amino-1,1-bisphosphonates derived from fatty acids against Trypanosoma cruzi targeting farnesyl pyrophosphate synthase
  作者：Sergio H. Szajnman、Esteban L. Ravaschino、Roberto Docampo、Juan B. Rodriguez

  DOI：10.1016/j.bmcl.2005.07.060

  日期：2005.11

  We have investigated the effect of a series of 1-amino-1,1-bisphosphonates derived from fatty acids against proliferation of the clinically more relevant form of Trypanosoma cruzi, the causative agent of American trypanosomiasis (Chagas' disease). Some of these drugs were potent inhibitors against the intracellular form of the parasite, exhibiting IC50 values at low micromolar level. Cellular activity was associated with the inhibition of enzymatic activity of T cruzi farnesyl pyrophosphate synthase. As bisphosphonate-containing drugs are FDA-approved for the treatment of bone resorption disorders, their potential innocuousness makes them good candidates to control tropical diseases. (c) 2005 Elsevier Ltd. All rights reserved.