Ethyl 3-(7-amino-4-chloro-6-methyl-1,3-dioxopyrrolo[3,4-c]pyridin-2-yl)propanoate | 175478-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: Ethyl 3-(7-amino-4-chloro-6-methyl-1,3-dioxopyrrolo[3,4-c]pyridin-2-yl)propanoate
• CAS: 175478-52-1
• 化学式: C₁₃H₁₄ClN₃O₄
• 分子量: 311.725
• InChiKey: IWCLHPXPWRDCKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 3-(7-amino-4-chloro-6-methyl-1,3-dioxopyrrolo[3,4-c]pyridin-2-yl)propanoate 在 盐酸 、 三乙胺 作用下， 反应 48.5h， 生成 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 、 beta-丙氨酸乙酯盐酸盐 反应 1.5h， 以35%的产率得到Ethyl 3-(7-amino-4-chloro-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

文献信息

• Synthesis of pyrrolo[3,4-c]pyridine derivatives possessing an acid group and their in vitro and in vivo evaluation as aldose reductase inhibitors
  作者：A Da Settimo、G Primofiore、F Da Settimo、F Simorini、C La Motta、A Martinelli、E Boldrini

  DOI：10.1016/s0223-5234(96)80006-7

  日期：1996.1

  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.