2-(2,3-dichlorophenyl)-1-hydroxyethylidenebisphosphonic acid | 1446450-25-4

• 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: 2-(2,3-dichlorophenyl)-1-hydroxyethylidenebisphosphonic acid
• 英文别名: [2-(2,3-Dichlorophenyl)-1-hydroxy-1-phosphonoethyl]phosphonic acid；[2-(2,3-dichlorophenyl)-1-hydroxy-1-phosphonoethyl]phosphonic acid
• CAS: 1446450-25-4
• 化学式: C₈H₁₀Cl₂O₇P₂
• 分子量: 351.017
• InChiKey: IMVYARZKKPINBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2,3-二氯苯乙酸 在 甲醇 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-(2,3-dichlorophenyl)-1-hydroxyethylidenebisphosphonic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Effective Inhibitors of Plant δ¹-Pyrroline-5-carboxylate Reductase

  摘要：

  Analogues of previously studied phenyl-substituted aminomethylene-bisphosphonic acids were synthesized and evaluated as inhibitors of Arabidopsis thaliana delta(1)-pyrroline-5-carboxylate reductase. With the aim of improving their effectiveness, two main modifications were introduced into the inhibitory scaffold: the aminomethylenebisphosphonic moiety was replaced with a hydroxymethylenebisphosphonic group, and the length of the molecule was increased by replacing the methylene linker with an ethylidene chain. In addition, chlorine atoms in the phenyl ring were replaced with various other substituents. Most of the studied derivatives showed activity in the rnicromolar to millimolar range, with two of them being more effective than the lead compound, with concentrations inhibiting 50% of enzyme activity as low as 50 mu M. Experimental evidence supporting the ability of these inhibitors to interfere with proline synthesis in vivo is also shown.

  DOI：

  10.1021/jf401234s

文献信息

• Synthesis and Evaluation of Effective Inhibitors of Plant δ¹-Pyrroline-5-carboxylate Reductase
  作者：Giuseppe Forlani、Łukasz Berlicki、Mattia Duò、Gabriela Dziędzioła、Samuele Giberti、Michele Bertazzini、Paweł Kafarski

  DOI：10.1021/jf401234s

  日期：2013.7.17

  Analogues of previously studied phenyl-substituted aminomethylene-bisphosphonic acids were synthesized and evaluated as inhibitors of Arabidopsis thaliana delta(1)-pyrroline-5-carboxylate reductase. With the aim of improving their effectiveness, two main modifications were introduced into the inhibitory scaffold: the aminomethylenebisphosphonic moiety was replaced with a hydroxymethylenebisphosphonic group, and the length of the molecule was increased by replacing the methylene linker with an ethylidene chain. In addition, chlorine atoms in the phenyl ring were replaced with various other substituents. Most of the studied derivatives showed activity in the rnicromolar to millimolar range, with two of them being more effective than the lead compound, with concentrations inhibiting 50% of enzyme activity as low as 50 mu M. Experimental evidence supporting the ability of these inhibitors to interfere with proline synthesis in vivo is also shown.