5-cyano-1-methyl-1H-pyrrole-2-carboxylic acid | 1378794-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-cyano-1-methyl-1H-pyrrole-2-carboxylic acid
• 英文别名: 5-cyano-1-methylpyrrole-2-carboxylic acid
• CAS: 1378794-76-3
• 化学式: C₇H₆N₂O₂
• 分子量: 150.137
• InChiKey: FRHZAVVAGSNTDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-Chloro-6-fluorophenyl)ethanamine 、 5-cyano-1-methyl-1H-pyrrole-2-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (S)-N-(1-(2-chloro-6-fluorophenyl)ethyl)-5-cyano-1-methyl-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Structure–activity relationship and liver microsome stability studies of pyrrole necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death pathway resulting in morphology reminiscent of passive nonregulated necrosis. Several diverse structure classes of necroptosis inhibitors have been reported to date, including a series of [1,2,3] thiadiazole benzylamide derivatives. However, initial evaluation of mouse liver microsome stability indicated that this series of compounds was rapidly degraded. A structure-activity relationship (SAR) study of the [1,2,3] thiadiazole benzylamide series revealed that increased mouse liver microsome stability and increased necroptosis inhibitory activity could be accomplished by replacement of the 4-cyclopropyl-[1,2,3] thiadiazole with a 5-cyano-1-methylpyrrole. In addition, the SAR and the cellular activity profiles, utilizing different cell types and necroptosis-inducing stimuli, of representative [1,2,3] thiadiazole and pyrrole derivatives were very similar suggesting that the two compound series inhibit necroptosis in the same manner. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.048
• 作为产物：
  描述：

  methyl 5-cyano-1-methyl-1H-pyrrole-2-carboxylate 在 甲醇 、 氢氧化钾 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 5-cyano-1-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Structure–activity relationship and liver microsome stability studies of pyrrole necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death pathway resulting in morphology reminiscent of passive nonregulated necrosis. Several diverse structure classes of necroptosis inhibitors have been reported to date, including a series of [1,2,3] thiadiazole benzylamide derivatives. However, initial evaluation of mouse liver microsome stability indicated that this series of compounds was rapidly degraded. A structure-activity relationship (SAR) study of the [1,2,3] thiadiazole benzylamide series revealed that increased mouse liver microsome stability and increased necroptosis inhibitory activity could be accomplished by replacement of the 4-cyclopropyl-[1,2,3] thiadiazole with a 5-cyano-1-methylpyrrole. In addition, the SAR and the cellular activity profiles, utilizing different cell types and necroptosis-inducing stimuli, of representative [1,2,3] thiadiazole and pyrrole derivatives were very similar suggesting that the two compound series inhibit necroptosis in the same manner. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.048

文献信息

• [EN] ISOXAZOLIDINE DERIVED INHIBITORS OF RECEPTOR INTERACTING PROTEIN KINASE 1 (RIPK 1)<br/>[FR] INHIBITEURS DÉRIVÉS D'ISOXAZOLIDINE DE PROTÉINE KINASE 1 INTERAGISSANT AVEC UN RÉCEPTEUR (RIPK 1)
  申请人：DENALI THERAPEUTICS INC

  公开号：WO2017096301A1

  公开（公告）日：2017-06-08

  The present disclosure relates generally to methods and compositions for preventing or arresting cell death and/or inflammation.

  本公开涉及一般用于预防或阻止细胞死亡和/或炎症的方法和组合物。
• Isoxazolidine derived inhibitors of receptor interacting protein kinase 1 (RIPK1)
  申请人：Denali Therapeutics Inc.

  公开号：US10709692B2

  公开（公告）日：2020-07-14

  The present disclosure relates generally to methods and compositions for preventing or arresting cell death and/or inflammation.

  本公开总体上涉及预防或阻止细胞死亡和/或炎症的方法和组合物。
• ISOXAZOLIDINE DERIVED INHIBITORS OF RECEPTOR INTERACTING PROTEIN KINASE 1 (RIPK1)
  申请人：Denali Therapeutics Inc.

  公开号：US20180353480A1

  公开（公告）日：2018-12-13

  The present disclosure relates generally to methods and compositions for preventing or arresting cell death and/or inflammation.