Dibenzyl 2-[[(2,3,4,5,6-pentafluorophenyl)methyl-phenylmethoxyphosphoryl]methyl]pentanedioate | 848952-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Dibenzyl 2-[[(2,3,4,5,6-pentafluorophenyl)methyl-phenylmethoxyphosphoryl]methyl]pentanedioate
• CAS: 848952-58-9
• 化学式: C₃₄H₃₀F₅O₆P
• 分子量: 660.574
• InChiKey: FHOSDRNTCCPUMT-UHFFFAOYSA-N

物化性质

• 沸点：
  681.1±65.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Dibenzyl 2-[[(2,3,4,5,6-pentafluorophenyl)methyl-phenylmethoxyphosphoryl]methyl]pentanedioate 在 5percent Pd/C 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 18.0h， 生成 2-[[(2,3,4,5,6-pentafluorobenzyl)hydroxy-phosphinyl]methyl]pentanedioic acid
  参考文献：
  名称：

  Design and Pharmacological Activity of Phosphinic Acid Based NAALADase Inhibitors

  摘要：

  A novel series of phosphinic acid based inhibitors of the neuropeptidase NAALADase are described in this work. This series of compounds is the most potent series of inhibitors of the enzyme described to date. In addition, we have shown that these compounds are protective in animal models of neurodegeneration. Compound 34 significantly prevented neurodegeneration in a middle cerebral artery occlusion model of cerebral ischemia. In addition, in the chronic constrictive mc del of neuropathic pain, compound 34 significantly attenuated the hypersensitivity observed with saline-treated animals. These data suggest that NAALADase inhibition may provide a new approach for the treatment of both neurodegenerative disorders and peripheral neuropathies.

  DOI：

  10.1021/jm0001774
• 作为产物：
  描述：

  α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 ammonium phosphite 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 Dibenzyl 2-[[(2,3,4,5,6-pentafluorophenyl)methyl-phenylmethoxyphosphoryl]methyl]pentanedioate
  参考文献：
  名称：

  Design and Pharmacological Activity of Phosphinic Acid Based NAALADase Inhibitors

  摘要：

  A novel series of phosphinic acid based inhibitors of the neuropeptidase NAALADase are described in this work. This series of compounds is the most potent series of inhibitors of the enzyme described to date. In addition, we have shown that these compounds are protective in animal models of neurodegeneration. Compound 34 significantly prevented neurodegeneration in a middle cerebral artery occlusion model of cerebral ischemia. In addition, in the chronic constrictive mc del of neuropathic pain, compound 34 significantly attenuated the hypersensitivity observed with saline-treated animals. These data suggest that NAALADase inhibition may provide a new approach for the treatment of both neurodegenerative disorders and peripheral neuropathies.

  DOI：

  10.1021/jm0001774

文献信息

• Design and Pharmacological Activity of Phosphinic Acid Based NAALADase Inhibitors
  作者：Paul F. Jackson、Kevin L. Tays、Keith M. Maclin、Yao-Sen Ko、Weixing Li、Dil Vitharana、Takashi Tsukamoto、Doris Stoermer、Xi-Chun M. Lu、Krystyna Wozniak、Barbara S. Slusher

  DOI：10.1021/jm0001774

  日期：2001.11.1

  A novel series of phosphinic acid based inhibitors of the neuropeptidase NAALADase are described in this work. This series of compounds is the most potent series of inhibitors of the enzyme described to date. In addition, we have shown that these compounds are protective in animal models of neurodegeneration. Compound 34 significantly prevented neurodegeneration in a middle cerebral artery occlusion model of cerebral ischemia. In addition, in the chronic constrictive mc del of neuropathic pain, compound 34 significantly attenuated the hypersensitivity observed with saline-treated animals. These data suggest that NAALADase inhibition may provide a new approach for the treatment of both neurodegenerative disorders and peripheral neuropathies.