1-(1-Phenylethyl)pyrrole-2-carboxylic acid | 1155519-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(1-Phenylethyl)pyrrole-2-carboxylic acid
• CAS: 1155519-30-4
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: BFLKSSGFEWKBMW-UHFFFAOYSA-N

物化性质

• 沸点：
  373.4±17.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-Phenylethyl)pyrrole-2-carboxylic acid 、 2-氯-6-氟苄胺 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 N-[(2-chloro-6-fluorophenyl)methyl]-1-(1-phenylethyl)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 1-(1-phenylethyl)-1H-pyrrole-2-carboxylate 在 甲醇 、 氢氧化钾 、 水 作用下， 反应 8.0h， 生成 1-(1-Phenylethyl)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

• ETOMIDATE ANALOGUES THAT DO NOT INHIBIT ADRENOCORTICAL STEROID SYNTHESIS
  申请人：The General Hospital Corporation

  公开号：EP2451779A2

  公开（公告）日：2012-05-16
• Compounds for Treating Disorders Associated with Abnormal Steroidogenesis
  申请人：The General Hospital Corporation

  公开号：US20200277264A1

  公开（公告）日：2020-09-03

  The present application provides compounds useful for treating disorders associated with abnormal steroidogenesis. Methods of treating disorders associated with abnormal steroidogenesis, methods of inhibiting 11β-hydroxylase activity, and pharmaceutical compositions comprising the compounds are also provided.
• US8765973B2
  申请人：——

  公开号：US8765973B2

  公开（公告）日：2014-07-01
• US9187421B2
  申请人：——

  公开号：US9187421B2

  公开（公告）日：2015-11-17
• [EN] ETOMIDATE ANALOGUES THAT DO NOT INHIBIT ADRENOCORTICAL STEROID SYNTHESIS<br/>[FR] ANALOGUES DE L'ÉTOMIDATE QUI N'INHIBENT PAS LA SYNTHÈSE DE STÉROÏDES CORTICOSURRÉNAUX
  申请人：GEN HOSPITAL CORP

  公开号：WO2011005969A2

  公开（公告）日：2011-01-13

  The invention is directed to compounds according to formula (I): where R1 is L1C(O)OT or L1C(O)OL2C(O)OT; R2 is a substituted or unsubstituted C1-C10 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl, or R1; n is an integer from 0 to 5; each R3 is independently halogen or R2; R4 and R5 are independently H, halogen, CN or CF3; L1 and L2 are each independently a bond, a substituted or unsubstituted C1-C10 alkylene, C2-C10 alkenylene, or C2-C10 alkynylene; and T is H, a substituted or unsubstituted C1-C10 alkyl, C2-C10 alkenyl, or C2-C10 alkynyl, nitrophenol, or cyclopropyl. The invention is also directed to a pharmaceutical composition comprising a compound according to formula (I) and a pharmaceutically acceptable carrier, and to methods for providing anesthesia in mammals by administering such a pharmaceutical composition.