2-(3,5-dimethylphenylamino)ethylidenebisphosphonic acid | 1446450-37-8

• 英文名称: 2-(3,5-dimethylphenylamino)ethylidenebisphosphonic acid
• 英文别名: [2-(3,5-Dimethylanilino)-1-phosphonoethyl]phosphonic acid
• CAS: 1446450-37-8
• 化学式: C₁₀H₁₇NO₆P₂
• 分子量: 309.196
• InChiKey: FWSAKEAJHGSSPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 三甲基溴硅烷 、 甲醇 作用下， 以 乙腈 为溶剂， 反应 14.0h， 生成 2-(3,5-dimethylphenylamino)ethylidenebisphosphonic 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