methyl 2-(1-benzyl-2-ethyl-1H-6,7-benzoindol-4-yloxy)acetate | 443911-39-5

• 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: methyl 2-(1-benzyl-2-ethyl-1H-6,7-benzoindol-4-yloxy)acetate
• 英文别名: 2-[(2-Ethyl-1-benzyl-1h-benz[g]indol-4-yl)oxy]acetic acid methyl ester；methyl 2-(1-benzyl-2-ethylbenzo[g]indol-4-yl)oxyacetate
• CAS: 443911-39-5
• 化学式: C₂₄H₂₃NO₃
• 分子量: 373.452
• InChiKey: XQUOBQMDVFAXDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  草酰氯 、 methyl 2-(1-benzyl-2-ethyl-1H-6,7-benzoindol-4-yloxy)acetate 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Highly Specific and Broadly Potent Inhibitors of Mammalian Secreted Phospholipases A₂

  摘要：

  We report a series of inhibitors of secreted phospholipases A(2) (sPLA(2)S) based on substituted indoles, 6,7-benzoindoles, and indolizines derived from LY315920, a well-known indole-based sPLA(2) inhibitor. Using the human group X sPLA2 crystal structure, we prepared a highly potent and selective indole-based inhibitor of this enzyme. Also, we report human and mouse group IIA and HE specific inhibitors and a substituted 6,7-benzoindole that inhibits nearly all human and mouse sPLAs in the low nanomolar range.

  DOI：

  10.1021/jm800422v
• 作为产物：
  描述：

  1-Benzyl-2-ethylbenzo[g]indol-4-ol 、 溴乙酸甲酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以23 mg的产率得到methyl 2-(1-benzyl-2-ethyl-1H-6,7-benzoindol-4-yloxy)acetate
  参考文献：
  名称：

  Highly Specific and Broadly Potent Inhibitors of Mammalian Secreted Phospholipases A₂

  摘要：

  We report a series of inhibitors of secreted phospholipases A(2) (sPLA(2)S) based on substituted indoles, 6,7-benzoindoles, and indolizines derived from LY315920, a well-known indole-based sPLA(2) inhibitor. Using the human group X sPLA2 crystal structure, we prepared a highly potent and selective indole-based inhibitor of this enzyme. Also, we report human and mouse group IIA and HE specific inhibitors and a substituted 6,7-benzoindole that inhibits nearly all human and mouse sPLAs in the low nanomolar range.

  DOI：

  10.1021/jm800422v

文献信息

• Novel spla2 inhibitors
  申请人：——

  公开号：US20040063967A1

  公开（公告）日：2004-04-01

  A novel class of benz[g]indole compounds is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of Inflammatory Diseases such as septic shock.

  揭示了一类新型苯[g]吲哚化合物，以及使用这些化合物来抑制sPLA2介导的脂肪酸释放，用于治疗炎症性疾病，如败血症。
• Spla2 inhibitors
  申请人：Beight Douglas Wade

  公开号：US06916840B2

  公开（公告）日：2005-07-12

  A novel class of benz[g]indole compounds is disclosed together with the use of such compounds for inhibiting sPLA2 mediated release of fatty acids for treatment of Inflammatory Diseases such as septic shock.

  本发明揭示了一类新型的苯[g]吲哚化合物，以及利用这些化合物抑制sPLA2介导的脂肪酸释放，用于治疗炎症性疾病，如感染性休克。
• BENZ(G) INDOLES AND THEIR USE AS SPLA2 INHIBITORS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1358156B1

  公开（公告）日：2007-02-21
• US6916840B2
  申请人：——

  公开号：US6916840B2

  公开（公告）日：2005-07-12
• Highly Specific and Broadly Potent Inhibitors of Mammalian Secreted Phospholipases A₂
  作者：Rob C. Oslund、Nathan Cermak、Michael H. Gelb

  DOI：10.1021/jm800422v

  日期：2008.8.1

  We report a series of inhibitors of secreted phospholipases A(2) (sPLA(2)S) based on substituted indoles, 6,7-benzoindoles, and indolizines derived from LY315920, a well-known indole-based sPLA(2) inhibitor. Using the human group X sPLA2 crystal structure, we prepared a highly potent and selective indole-based inhibitor of this enzyme. Also, we report human and mouse group IIA and HE specific inhibitors and a substituted 6,7-benzoindole that inhibits nearly all human and mouse sPLAs in the low nanomolar range.