3-benzyl-5-(1H-indol-3-yl)-1,2,4-oxadiazole | 422564-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-benzyl-5-(1H-indol-3-yl)-1,2,4-oxadiazole
• 英文别名: 3-(3-Benzyl-[1,2,4]oxadiazol-5-yl)-1H-indole
• CAS: 422564-77-0
• 化学式: C₁₇H₁₃N₃O
• 分子量: 275.31
• InChiKey: NUOCNLYLZMZBSS-UHFFFAOYSA-N

物化性质

• 熔点：
  198-199 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  525.1±60.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyl-5-(1H-indol-3-yl)-1,2,4-oxadiazole 、 N-(2-氯乙基)吗啉盐酸盐 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以14.9%的产率得到3-(3-Benzyl-[1,2,4]-oxadiazol-5-yl)-1-[2-(morpholin-4-yl)ethyl]-1H-indole
  参考文献：
  名称：

  Synthesis and cannabinoid activity of 1-substituted-indole-3-oxadiazole derivatives: Novel agonists for the CB1 receptor

  摘要：

  An exploratory chemical effort has been undertaken to develop a novel series of compounds as selective CB1 agonists. It is hoped that compounds of this type will have clinical utility in pain control, and cerebral ischaemia following stroke or traumatic head injury.We report here medicinal chemistry studies directed towards the investigation of a series of 1-substituted-indole-3-oxadiazoles as potential CB, agonists. Crown Copyright (c) 2007 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.04.007
• 作为产物：
  描述：

  3-吲哚甲酸 、 N’-羟基-2-苯基ETHANIMIDAMIDE 在 3 A molecular sieve 、 sodium hydride 、 N,N'-羰基二咪唑 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以51%的产率得到3-benzyl-5-(1H-indol-3-yl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis and cannabinoid activity of 1-substituted-indole-3-oxadiazole derivatives: Novel agonists for the CB1 receptor

  摘要：

  An exploratory chemical effort has been undertaken to develop a novel series of compounds as selective CB1 agonists. It is hoped that compounds of this type will have clinical utility in pain control, and cerebral ischaemia following stroke or traumatic head injury.We report here medicinal chemistry studies directed towards the investigation of a series of 1-substituted-indole-3-oxadiazoles as potential CB, agonists. Crown Copyright (c) 2007 Published by Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.04.007

文献信息

• 3-Oxadiazol-5-yl-1-aminoalkyl-1h-indole derivatives
  申请人：——

  公开号：US20040034073A1

  公开（公告）日：2004-02-19

  The invention provides aminoalkylindole compounds of Formula (I), wherein R 1 -R 5 , n and p are as described. Also provided are compositions containing compounds of Formula (I) and the use of compounds of Formula (I) in modulating the activity of a cannabinoid receptor in a subject. In particular, the invention provides the use of such compounds as analgesic agents. 1

  该发明提供了公式(I)的氨基烷基吲哚化合物，其中R1-R5、n和p如所述。还提供了含有公式(I)化合物的组合物，以及在调节受体活性中使用公式(I)化合物的方法。具体来说，该发明提供了将这类化合物用作镇痛剂的用途。
• 3-OXADIAZOL-5-YL-1-AMINOALKYL-1H-INDOLE DERIVATIVES
  申请人：Amrad Operations Pty.,Ltd.

  公开号：EP1339710B1

  公开（公告）日：2006-03-01
• EP1339710A4
  申请人：——

  公开号：EP1339710A4

  公开（公告）日：2004-05-12
• US6930118B2
  申请人：——

  公开号：US6930118B2

  公开（公告）日：2005-08-16
• [EN] 3-OXADIAZOL-5-YL-1-AMINOALKYL-1H-INDOLE DERIVATIVES<br/>[FR] DERIVES DU 3-OXADIAZOL-5-YL-1-AMINOALKYL-1H-INDOLE
  申请人：AMRAD OPERATIONS PTY LTD

  公开号：WO2002036590A1

  公开（公告）日：2002-05-10

  The invention provides aminoalkylindole compounds of Formula (I), wherein R1-R5, n and p are as described. Also provided are compositions containing compounds of Formula (I) and the use of compounds of Formula (I) in modulating the activity of a cannabinoid receptor in a subject. In particular, the invention provides the use of such compounds as analgesic agents.