[(4-Bromo-phenyl)-hydroxy-phosphono-methyl]-phosphonic acid | 865879-46-5

• 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: [(4-Bromo-phenyl)-hydroxy-phosphono-methyl]-phosphonic acid
• 英文别名: [(4-bromophenyl)(hydroxy)methylene]bis(phosphonic acid)；[(4-Bromophenyl)-hydroxy-phosphonomethyl]phosphonic acid
• CAS: 865879-46-5
• 化学式: C₇H₉BrO₇P₂
• 分子量: 346.996
• InChiKey: OQZSNMSDUQXRSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C
• 沸点：
  700.3±70.0 °C(Predicted)
• 密度：
  2.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-甲基吡啶 、 copper(II) perchlorate hexahydrate 、 [(4-Bromo-phenyl)-hydroxy-phosphono-methyl]-phosphonic acid 以 甲醇 为溶剂， 以19%的产率得到
  参考文献：
  名称：

  [（4-溴苯基）（羟基）亚甲基]双（膦酸）四核铜配合物的合成，晶体结构和磁性

  摘要：

  摘要四核Cu（II）络合物[Cu4（3-Mepy）8（H2L）2（ClO4）2]·（3-Mepy）2·（H2O）2（1），其中H5L = [（4-溴苯基）制备（羟基）亚甲基]双（膦酸）和3-Mepy = 3-甲基吡啶，并通过元素分析，FT-IR光谱，单晶X射线分析和磁测量进行表征。DFT理论计算支持的1的磁性能分析表明，铁磁交换（J2 = J3 = 20.0 cm-1）与反铁磁交换（J1 = -64.4 cm-1）之间存在相互作用，从而导致S = 0的自旋态。

  DOI：

  10.1016/j.ica.2020.119689
• 作为产物：
  描述：

  4-溴苯甲酰氯 在 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [(4-Bromo-phenyl)-hydroxy-phosphono-methyl]-phosphonic acid
  参考文献：
  名称：

  Bisphosphonate prodrugs: Synthesis and biological evaluation in HuH7 hepatocarcinoma cells

  摘要：

  We investigated the biological effects of new synthesized bisphosphonates (BPs) on HuH7 hepatocarcinoma cells. BPs containing p-bromophenyl (R-1 = p-Br, Ph, 2) in their side chain were the more potent to inhibit HuH7 cell viability. In addition, phenyl diesterified analogues (R-2 = R-3 = Ph, 2a) were more potent than methyl (R-2 = R-3 = Me, 2b) or non-esterified BPs (2) inducing more necrosis suggesting that they better entered into cells. Phosphodiesterase inhibitor (IBMX) reversed the effect of the esterified BPs and not that of non-esterified ones suggesting role of cell phosphodiesterases to release active BPs. BP analogues inhibited HuH7 cell migration but esterified ones had no effect on invasion due to the hiding of phosphonic groups. All together, these results indicated the therapeutic interest of these new BP prodrugs. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.054

文献信息

• Bisphosphonate prodrugs: Synthesis and biological evaluation in HuH7 hepatocarcinoma cells
  作者：Maelle Monteil、Evelyne Migianu-Griffoni、Odile Sainte-Catherine、Mélanie Di Benedetto、Marc Lecouvey

  DOI：10.1016/j.ejmech.2014.02.054

  日期：2014.4

  We investigated the biological effects of new synthesized bisphosphonates (BPs) on HuH7 hepatocarcinoma cells. BPs containing p-bromophenyl (R-1 = p-Br, Ph, 2) in their side chain were the more potent to inhibit HuH7 cell viability. In addition, phenyl diesterified analogues (R-2 = R-3 = Ph, 2a) were more potent than methyl (R-2 = R-3 = Me, 2b) or non-esterified BPs (2) inducing more necrosis suggesting that they better entered into cells. Phosphodiesterase inhibitor (IBMX) reversed the effect of the esterified BPs and not that of non-esterified ones suggesting role of cell phosphodiesterases to release active BPs. BP analogues inhibited HuH7 cell migration but esterified ones had no effect on invasion due to the hiding of phosphonic groups. All together, these results indicated the therapeutic interest of these new BP prodrugs. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis, crystal structure and magnetic properties of tetranuclear copper complex based on [(4-bromophenyl)(hydroxy)methylene]bis(phosphonic acid)
  作者：Barbora Rybníčková、Juraj Kuchár、Peter Antal、Radovan Herchel

  DOI：10.1016/j.ica.2020.119689

  日期：2020.9

  Abstract The tetranuclear Cu(II) complex [Cu4(3-Mepy)8(H2L)2(ClO4)2]·(3-Mepy)2·(H2O)2 (1), where H5L = [(4-bromophenyl)(hydroxy)methylene]bis(phosphonic acid) and 3-Mepy = 3-methylpyridine, was prepared and characterized by elemental analysis, FT-IR spectroscopy, single-crystal X-ray analysis and magnetic measurements. The analysis of magnetic properties of 1 supported by DFT theoretical calculations

  摘要四核Cu（II）络合物[Cu4（3-Mepy）8（H2L）2（ClO4）2]·（3-Mepy）2·（H2O）2（1），其中H5L = [（4-溴苯基）制备（羟基）亚甲基]双（膦酸）和3-Mepy = 3-甲基吡啶，并通过元素分析，FT-IR光谱，单晶X射线分析和磁测量进行表征。DFT理论计算支持的1的磁性能分析表明，铁磁交换（J2 = J3 = 20.0 cm-1）与反铁磁交换（J1 = -64.4 cm-1）之间存在相互作用，从而导致S = 0的自旋态。