Ethyl 2-chloro-5-vinylbenzoate | 1251530-44-5

• 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 2-chloro-5-vinylbenzoate
• 英文别名: ethyl 2-chloro-5-ethenylbenzoate
• CAS: 1251530-44-5
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: WTPNCNOLASWQDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl 2-chloro-5-vinylbenzoate 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 1,3-双(二苯基膦)丙烷 、 频那醇硼烷 、 sodium perborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 以69%的产率得到
  参考文献：
  名称：

  Addressing time-dependent CYP 3A4 inhibition observed in a novel series of substituted amino propanamide renin inhibitors, a case study

  摘要：

  Time-dependent inhibitors of CYPs have the potential to perpetrate drug-drug interactions in the clinical setting. After finding that several leading compounds in a novel series of substituted amino propanamide renin inhibitors inactivated CYP3A4 in an NADPH-dependent and time-dependent manner, a search to identify the cause of this liability was initiated. Extensive SAR revealed that the amide bridge present in compound 1 as a possible culprit. Through the installation of a metabolic soft spot distal to this moiety, potent renin inhibitors with improved CYP profile were identified. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.030
• 作为产物：
  描述：

  乙烯基硼酸频哪醇酯 、 5-溴-2-氯苯甲酸乙酯 在 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以86%的产率得到Ethyl 2-chloro-5-vinylbenzoate
  参考文献：
  名称：

  Addressing time-dependent CYP 3A4 inhibition observed in a novel series of substituted amino propanamide renin inhibitors, a case study

  摘要：

  Time-dependent inhibitors of CYPs have the potential to perpetrate drug-drug interactions in the clinical setting. After finding that several leading compounds in a novel series of substituted amino propanamide renin inhibitors inactivated CYP3A4 in an NADPH-dependent and time-dependent manner, a search to identify the cause of this liability was initiated. Extensive SAR revealed that the amide bridge present in compound 1 as a possible culprit. Through the installation of a metabolic soft spot distal to this moiety, potent renin inhibitors with improved CYP profile were identified. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.030

文献信息

• [EN] HEDGEHOG PATHWAY ANTAGONISTS AND THERAPEUTIC APPLICATIONS THEREOF<br/>[FR] ANTAGONISTES DE LA VOIE HEDGEHOG ET LEURS APPLICATIONS THÉRAPEUTIQUES
  申请人：SIENA BIOTECH SPA

  公开号：WO2009074300A2

  公开（公告）日：2009-06-18

  Heterocyclic compounds that modulate the hedgehog signaling pathway, pharmaceutical composition thereof and their therapeutic applications.
• Addressing time-dependent CYP 3A4 inhibition observed in a novel series of substituted amino propanamide renin inhibitors, a case study
  作者：Austin Chen、Daniel Dubé、Laurence Dubé、Sébastien Gagné、Michel Gallant、Mireille Gaudreault、Erich Grimm、Robert Houle、Patrick Lacombe、Sébastien Laliberté、Suzanna Liu、Dwight MacDonald、Bruce Mackay、David Martin、Dan McKay、David Powell、Jean-François Lévesque

  DOI：10.1016/j.bmcl.2010.07.030

  日期：2010.9

  Time-dependent inhibitors of CYPs have the potential to perpetrate drug-drug interactions in the clinical setting. After finding that several leading compounds in a novel series of substituted amino propanamide renin inhibitors inactivated CYP3A4 in an NADPH-dependent and time-dependent manner, a search to identify the cause of this liability was initiated. Extensive SAR revealed that the amide bridge present in compound 1 as a possible culprit. Through the installation of a metabolic soft spot distal to this moiety, potent renin inhibitors with improved CYP profile were identified. (C) 2010 Elsevier Ltd. All rights reserved.