Ethyl 3-[4-chloro-7-[(4-fluorobenzoyl)amino]-6-methyl-1,3-dioxopyrrolo[3,4-c]pyridin-2-yl]propanoate | 175478-60-1

• 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: Ethyl 3-[4-chloro-7-[(4-fluorobenzoyl)amino]-6-methyl-1,3-dioxopyrrolo[3,4-c]pyridin-2-yl]propanoate
• CAS: 175478-60-1
• 化学式: C₂₀H₁₇ClFN₃O₅
• 分子量: 433.823
• InChiKey: WADYATXVPQQXDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 3-[4-chloro-7-[(4-fluorobenzoyl)amino]-6-methyl-1,3-dioxopyrrolo[3,4-c]pyridin-2-yl]propanoate 在 盐酸 作用下， 反应 0.5h， 以74%的产率得到3-[4-Chloro-7-[(4-fluorobenzoyl)amino]-6-methyl-1,3-dioxopyrrolo[3,4-c]pyridin-2-yl]propanoic acid
  参考文献：
  名称：

  Synthesis of pyrrolo[3,4-c]pyridine derivatives possessing an acid group and their in vitro and in vivo evaluation as aldose reductase inhibitors

  摘要：

  Derivatives of [pyrrolo[3,4-c]pyridin-1,3(2H)-dion-2-yl] alkanoic acids were prepared and their in vitro aldose reductase inhibitory activity was tested on rat lens enzyme. The acetic derivatives 2, 5 and 15a-d proved to be much more potent inhibitors than the propionic derivatives, 7 and 16a-d, and the iso-propionic derivatives, 3 and 6. The presence of a second planar aromatic area in the benzoyl derivatives 15a-d did not result in any increase in activity. Two of the most active compounds in vitro (2 and 5) were also evaluated in vivo as inhibitors of glutathione lens depletion in galactosemic rats. None of the compounds was found to be active in maintaining the rat lens glutathione level, suggesting possible problems of ocular bioavailability and metabolism. The aldose reductase inhibitory activity of compounds 2 and 15d was also discussed by taking into account their conformational and electronic characteristics evaluated by means of theoretical calculations.

  DOI：

  10.1016/s0223-5234(96)80006-7
• 作为产物：
  描述：

  3-氨基-6-氯-2-甲基吡啶-4,5-二羧酸 在 三乙胺 作用下， 反应 49.5h， 生成 Ethyl 3-[4-chloro-7-[(4-fluorobenzoyl)amino]-6-methyl-1,3-dioxopyrrolo[3,4-c]pyridin-2-yl]propanoate
  参考文献：
  名称：

  Synthesis of pyrrolo[3,4-c]pyridine derivatives possessing an acid group and their in vitro and in vivo evaluation as aldose reductase inhibitors

  摘要：

  Derivatives of [pyrrolo[3,4-c]pyridin-1,3(2H)-dion-2-yl] alkanoic acids were prepared and their in vitro aldose reductase inhibitory activity was tested on rat lens enzyme. The acetic derivatives 2, 5 and 15a-d proved to be much more potent inhibitors than the propionic derivatives, 7 and 16a-d, and the iso-propionic derivatives, 3 and 6. The presence of a second planar aromatic area in the benzoyl derivatives 15a-d did not result in any increase in activity. Two of the most active compounds in vitro (2 and 5) were also evaluated in vivo as inhibitors of glutathione lens depletion in galactosemic rats. None of the compounds was found to be active in maintaining the rat lens glutathione level, suggesting possible problems of ocular bioavailability and metabolism. The aldose reductase inhibitory activity of compounds 2 and 15d was also discussed by taking into account their conformational and electronic characteristics evaluated by means of theoretical calculations.

  DOI：

  10.1016/s0223-5234(96)80006-7