Methyl 5-[(2-chloro-6-fluorophenyl)methylsulfamoyl]-1-methylpyrrole-2-carboxylate | 1041644-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Methyl 5-[(2-chloro-6-fluorophenyl)methylsulfamoyl]-1-methylpyrrole-2-carboxylate
• CAS: 1041644-26-1
• 化学式: C₁₄H₁₄ClFN₂O₄S
• 分子量: 360.794
• InChiKey: AXRQGUHBCDZXLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 5-[(2-chloro-6-fluorophenyl)methylsulfamoyl]-1-methylpyrrole-2-carboxylate 在 氨 、 三甲基铝 作用下， 以 正己烷 、 氯苯 为溶剂， 反应 48.0h， 生成 N-[(2-chloro-6-fluorophenyl)methyl]-5-cyano-1-methylpyrrole-2-sulfonamide 、
  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：

  5-氯磺酰-1-甲基-1H-吡咯-2-羧酸甲酯 、 2-氯-6-氟苄胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以95%的产率得到Methyl 5-[(2-chloro-6-fluorophenyl)methylsulfamoyl]-1-methylpyrrole-2-carboxylate
  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