diethyl [(2-hydroxyphenyl)(4-bromophenylamino)methyl]phosphonate | 1363568-19-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diethyl [(2-hydroxyphenyl)(4-bromophenylamino)methyl]phosphonate
• 英文别名: diethyl (4-bromophenylamino)(2-hydroxyphenyl)methylphosphonate；2-[(4-Bromoanilino)-diethoxyphosphorylmethyl]phenol
• CAS: 1363568-19-7
• 化学式: C₁₇H₂₁BrNO₄P
• 分子量: 414.236
• InChiKey: IGLFQKPVXIZQFX-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

• 作为反应物：
  描述：

  diethyl [(2-hydroxyphenyl)(4-bromophenylamino)methyl]phosphonate 、 亚磷酸二乙酯 在 四氯化碳 、 三乙胺 作用下， 反应 0.5h， 以88%的产率得到
  参考文献：
  名称：

  新一代有前途的磷酸盐 α-氨基膦酸盐：设计、合成、体外生物学评价和计算研究

  摘要：

  通过Kabachnik-Fields和Atherton-Todd 反应的序列多组分反应策略合成了一类新的磷酸盐 - 膦酸酯化合物。所有设计的产品都在较短的反应时间内以良好的化学产率获得，并通过光谱分析证实。[(4-二乙基磷酸苯基)(4-三氟甲基苯基氨基)甲基]膦酸二乙酯6g通过单晶 X 射线分析表征。这些化合物表现出很强的抗真菌作用，对 AChE 的抑制作用很低，对 BChE 没有抑制活性，具有令人感兴趣的抗氧化能力。结果使它们成为有希望的原始有机磷农药候选物。关于各种构象异构体的相对稳定性的 DFT 计算，以及所选化合物的测量和计算 NMR 谱的比较；表明在这种类型的分子中很容易发生构象相互转换，因此同一化合物的许多结构可以在溶液中共存。

  DOI：

  10.1016/j.molstruc.2021.131336
• 作为产物：
  描述：

  邻羟苯亚甲基对溴苯胺 、 亚磷酸二乙酯 以 乙醇 为溶剂， 以30%的产率得到diethyl [(2-hydroxyphenyl)(4-bromophenylamino)methyl]phosphonate
  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

• 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.
• New promising generation of phosphates α-aminophosphonates: Design, synthesis, in-vitro biological evaluation and computational study
  作者：Rim Aissa、Samia Guezane-Lakoud、Lynda Gali、Martial Toffano、Anna Ignaczak、Marta Adamiak、Mounia Merabet-Khelassi、Regis Guillot、Louisa Aribi-Zouioueche

  DOI：10.1016/j.molstruc.2021.131336

  日期：2022.1

  candidates as original organophosphorus pesticides. The DFT calculations concerning relative stability of various conformers, besides the comparison of the measured and calculated NMR spectra of selected compounds; suggest that conformational interconversion can quite easily occur in this type of molecules, so that many structures of the same compound can coexist in solution.

  通过Kabachnik-Fields和Atherton-Todd 反应的序列多组分反应策略合成了一类新的磷酸盐 - 膦酸酯化合物。所有设计的产品都在较短的反应时间内以良好的化学产率获得，并通过光谱分析证实。[(4-二乙基磷酸苯基)(4-三氟甲基苯基氨基)甲基]膦酸二乙酯6g通过单晶 X 射线分析表征。这些化合物表现出很强的抗真菌作用，对 AChE 的抑制作用很低，对 BChE 没有抑制活性，具有令人感兴趣的抗氧化能力。结果使它们成为有希望的原始有机磷农药候选物。关于各种构象异构体的相对稳定性的 DFT 计算，以及所选化合物的测量和计算 NMR 谱的比较；表明在这种类型的分子中很容易发生构象相互转换，因此同一化合物的许多结构可以在溶液中共存。