[氨基-(2,4-二氯苯基)甲基]膦酸 | 125553-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [氨基-(2,4-二氯苯基)甲基]膦酸
• 英文名称: [amino-(2,4-dichlorophenyl)methyl]phosphonic acid
• 英文别名: Phosphonic acid, [amino(2,4-dichlorophenyl)methyl]-
• CAS: 125553-07-3
• 化学式: C₇H₈Cl₂NO₃P
• mdl: MFCD30149678
• 分子量: 256.025
• InChiKey: QXOFDXPCBBHAHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二氯苯甲醛 在 乙酰胺 、 溶剂黄146 、 乙酰氯 、 三氯化磷 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以72%的产率得到[氨基-(2,4-二氯苯基)甲基]膦酸
  参考文献：
  名称：

  取代的苯基甘氨酸的膦酸类似物作为马铃薯苯丙氨酸氨裂合酶的抑制剂。

  摘要：

  已经合成了一系列在苯环上被各种取代的苯基甘氨酸的膦酸类似物，并评估了它们对马铃薯1-苯基丙氨酸氨裂合酶的抑制活性。大多数化合物似乎充当该酶的中度（微摩尔）抑制剂。使用分子模型进行的结合分析表明，它们可能结合在酶的活性位点或非生理位点。后者位于邻近的深位点，靠近底物进入活性位点的进入通道。

  DOI：

  10.1016/j.biochi.2018.06.005

文献信息

• A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds
  作者：Ayhan S. Demir、Cihangir Tanyeli、Özge Şeşenoǧlu、Şerafettin Demiç、Özden Özel Evin

  DOI：10.1016/0040-4039(95)02171-x

  日期：1996.1

  A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroxyiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1- aminophosphonates gave 1-aminophosphonic acids in good yield.
• Tailoring the Structure of Aminobisphosphonates To Target Plant P5C Reductase
  作者：Giuseppe Forlani、Andrea Occhipinti、Łukasz Berlicki、Gabriela Dziedzioła、Anna Wieczorek、Paweł Kafarski

  DOI：10.1021/jf800029t

  日期：2008.5.1

  Using the structure of (3,5-dichlorophenyl)aminomethylenebisphosphonic acid as a lead compound, 25 new phosphonates were synthesized and evaluated as possible inhibitors of Arabidopsis thaliana delta(1)-pyrroline-5-carboxylate (P5C) reductase. Derivatives substituted in the phenyl ring retained the inhibitory potential, though to a different extent. On the contrary any variation in the scaffold, i.e., the replacement of the second phosphonate moiety with a hydroxyl or an amino residue, resulted in a significant loss of biological activity. The availability of several structures capable of interfering with the catalytic mechanism in the micromolar to millimolar range allowed a proper structure-activity relationship analysis, leading us to hypothesize about the steric and electronic requirements for maintenance or enhancement of the inhibitory properties. Reversal experiments with suspension cultured cells provided evidence for the occurrence of enzyme inhibition in vivo. Because in higher plants the step catalyzed by P5C reductase is shared by all pathways leading to proline synthesis, these compounds may be exploited for the design of new substances endowed with herbicidal activity.
• Substituted phosphonic analogues of phenylglycine as inhibitors of phenylalanine ammonia lyase from potatoes
  作者：Weronika Wanat、Michał Talma、Józef Hurek、Małgorzata Pawełczak、Paweł Kafarski

  DOI：10.1016/j.biochi.2018.06.005

  日期：2018.8

  A series of phosphonic acid analogues of phenylglycine variously substituted in phenyl ring have been synthesized and evaluated for their inhibitory activity towards potato l-phenylalanine ammonia lyase. Most of the compounds appeared to act as moderate (micromolar) inhibitors of the enzyme. Analysis of their binding performed using molecular modeling have shown that they might be bound either in active

  已经合成了一系列在苯环上被各种取代的苯基甘氨酸的膦酸类似物，并评估了它们对马铃薯1-苯基丙氨酸氨裂合酶的抑制活性。大多数化合物似乎充当该酶的中度（微摩尔）抑制剂。使用分子模型进行的结合分析表明，它们可能结合在酶的活性位点或非生理位点。后者位于邻近的深位点，靠近底物进入活性位点的进入通道。