diethyl (4-chlorophenylamino)(2-hydroxyphenyl)methylphosphonate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diethyl (4-chlorophenylamino)(2-hydroxyphenyl)methylphosphonate
• 英文别名: 2-[(4-Chloroanilino)-diethoxyphosphorylmethyl]phenol
• 化学式: C₁₇H₂₁ClNO₄P
• 分子量: 369.785
• InChiKey: GZVWNCRETSUTMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-([(4-氯苯基)亚氨基]甲基)苯酚 、 亚磷酸二乙酯 以 乙醇 为溶剂， 以32%的产率得到diethyl (4-chlorophenylamino)(2-hydroxyphenyl)methylphosphonate
  参考文献：
  名称：

  Exploration of α-aminophosphonate N-derivatives as novel, potent and selective inhibitors of protein tyrosine phosphatases

  摘要：

  Seventeen alpha-aminophosphonates are synthesized. Their compositions and structures are established by EA, UV, FT-IR, H-1 NMR, C-13 NMR, P-31 NMR and ESI-MS. Compounds 1-4 are confirmed by X-ray crystallography. PIP inhibition shows compounds 1-5, 12, 15 are moderate competitive inhibitors with some selectivity. The most potent inhibitor is compound 5 with the lowest IC50 value about 6.64 mu M against PTP1B, about 2-fold and 25-fold stronger than against TCPTP and PTP-MEG2 while it doesn't inhibit SHP-1 and SHP-2. The binding constant of 5 to PTP1B is 2.23 x 10(5) M-1 and binding ratio approximates 1:1. Cell viability and apoptosis assays indicate 5 is cell permeable with lower cytotoxicity. The results indicate alpha-aminophosphonates are possibly developed to effective and selective inhibitors of PTPs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.038

文献信息

• Zr4+-Catalyzed Efficient Synthesis of α-Aminophosphonates
  作者：J. S. Yadav、B. V. S. Reddy、K. Sarita Raj、K. Bhaskar Reddy、A. R. Prasad

  DOI：10.1055/s-2001-18444

  日期：——

  Aldimines undergo nucleophilic addition with diethyl phosphite in the presence of a catalytic amount of zirconium tetrachloride at ambient temperature to afford the corresponding α-aminophosphonates in high yields with high selectivity.

  在环境温度下，在催化量的四氯化锆存在下，醛亚胺与亚磷酸二乙酯发生亲核加成反应，以高收率和高选择性得到相应的 α-氨基膦酸酯。
• Catalyst and solvent-free, ultrasound promoted rapid protocol for the one-pot synthesis of α-aminophosphonates at room temperature
  作者：Bashir Dar、Amrinder Singh、Akshya Sahu、Praveen Patidar、Arup Chakraborty、Meena Sharma、Baldev Singh

  DOI：10.1016/j.tetlet.2012.07.123

  日期：2012.10

  An ultrasound promoted easy, efficient, and environment friendly process has been devised for the synthesis of α-aminophosphonates within seconds through a one-pot three-component condensation of the aldehydes, amines, and triethylphosphite. The desired products were obtained in excellent yields and in high purity under solvent-free and catalyst-free conditions. Study with various aldehydes and amines

  已经设计了超声促进的简单，有效和环境友好的方法，用于通过醛，胺和亚磷酸三乙酯的一锅式三组分缩合在几秒钟内合成α-氨基膦酸酯。在无溶剂和无催化剂的条件下，可以以极高的收率和高纯度获得所需的产物。对各种醛和胺的研究表明，超声辐射在α-氨基膦酸酯的直接合成中起着关键作用。
• Exploration of α-aminophosphonate N-derivatives as novel, potent and selective inhibitors of protein tyrosine phosphatases
  作者：Qingming Wang、Miaoli Zhu、Ruiting Zhu、Liping Lu、Caixia Yuan、Shu Xing、Xueqi Fu、Yuhua Mei、Qingwei Hang

  DOI：10.1016/j.ejmech.2012.01.038

  日期：2012.3

  Seventeen alpha-aminophosphonates are synthesized. Their compositions and structures are established by EA, UV, FT-IR, H-1 NMR, C-13 NMR, P-31 NMR and ESI-MS. Compounds 1-4 are confirmed by X-ray crystallography. PIP inhibition shows compounds 1-5, 12, 15 are moderate competitive inhibitors with some selectivity. The most potent inhibitor is compound 5 with the lowest IC50 value about 6.64 mu M against PTP1B, about 2-fold and 25-fold stronger than against TCPTP and PTP-MEG2 while it doesn't inhibit SHP-1 and SHP-2. The binding constant of 5 to PTP1B is 2.23 x 10(5) M-1 and binding ratio approximates 1:1. Cell viability and apoptosis assays indicate 5 is cell permeable with lower cytotoxicity. The results indicate alpha-aminophosphonates are possibly developed to effective and selective inhibitors of PTPs. (C) 2012 Elsevier Masson SAS. All rights reserved.