2-(benzylthio)-5-(1H-indol-2-yl)-1,3,4-oxadiazole | 1207254-75-8

• 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: 2-(benzylthio)-5-(1H-indol-2-yl)-1,3,4-oxadiazole
• 英文别名: 2-benzylsulfanyl-5-(1H-indol-2-yl)-1,3,4-oxadiazole
• CAS: 1207254-75-8
• 化学式: C₁₇H₁₃N₃OS
• 分子量: 307.376
• InChiKey: PGXLGSGDZWFUGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(1H-indol-2-yl)-1,3,4-oxadiazole-2(3H)-thione 、 溴甲苯 在 三乙胺 作用下， 以 丙酮 为溶剂， 以90%的产率得到2-(benzylthio)-5-(1H-indol-2-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis of New Functionalized 2-Alkylsulfanyl-5-(1H-indol-2-yl)-1,3,4- Oxadiazole and a Facile Thio-Aza-Claisen Rearrangement of the S-Allyl Analog

  摘要：

  通过使用三乙胺（TEA）作为酸捕获剂，5-(1H-吲哚-2-基)-1,3,4-噁二唑-2(3H)-硫酮1的烷基化反应，区域选择性地合成了S-烷基化的吲哚噁二唑2a-l。1与溴丙烷、溴丁烷、溴十一烷在碳酸钾存在下反应，除了生成S-烷基化类似物2i-j,m外，还生成了N-烷基化产物3i-j,m。S-烯丙基噁二唑2k通过简便的硫-氮-Claisen重排（S→N烯丙基重排），以优异的产率转化为N-烯丙基类似物3k。进一步在碳酸钾存在下对2k和3k进行烯丙基化反应，分别产生吲哚环NH的烯丙基化产物5和6。在碳酸钾存在下，1的苄基化反应生成了7，且苄基未发生S→N迁移。1H NMR、13C NMR和质谱证实了结构，并区分了N-和S-烷基化产物。

  DOI：

  10.2174/157017809789124902

文献信息

• [EN] INDOLE-OXADIAZOLE COMPOUNDS AND THEIR THERAPEUTIC USE<br/>[FR] COMPOSÉS D'INDOLE-OXADIAZOLE ET LEUR UTILISATION THÉRAPEUTIQUE
  申请人：GOVERNING COUNCIL UNIV TORONTO

  公开号：WO2020051707A1

  公开（公告）日：2020-03-19

  The present application pertains to methods of using indole-oxadiazole compounds of Formula I to modulate cannabinoid receptor activity: I In particular diseases, disorders or conditions that benefit from modulating cannabinoid receptor activity, such as non-alcoholic steatohepatitis (NASH), non-alcoholic fatty liver disease (NAFLD), schizophrenia, bipolar disorder, psychosis, metabolic syndrome, type-2 diabetes, dyslipidaemia, obesity, eating disorders, cardiovascular diseases and disorders, and other conditions as described herein, may be treated. Also included in the present application are certain novel compounds of Formula Ia and pharmaceutical compositions comprising these compounds.

  本申请涉及使用式I的吲哚-噁二唑化合物调节大麻素受体活性的方法：I 特别是在需要调节大麻素受体活性的疾病、障碍或病况，例如非酒精性脂肪性肝炎（NASH）、非酒精性脂肪肝病（NAFLD）、精神分裂症、躁郁症、精神病、代谢综合征、2型糖尿病、血脂异常、肥胖症、进食障碍、心血管疾病和其他如本文所述的病症，可以得到治疗。本申请还包括式Ia的某些新化合物和包含这些化合物的制药组合物。
• INDOLE-OXADIAZOLE COMPOUNDS AND THEIR THERAPEUTIC USE
  申请人：THE GOVERNING COUNCIL OF THE UNIVERSITY OF TORONTO

  公开号：US20220257569A1

  公开（公告）日：2022-08-18

  The present application pertains to methods of using indole-oxadiazole compounds of Formula I to modulate cannabinoid receptor activity: I In particular diseases, disorders or conditions that benefit from modulating cannabinoid receptor activity, such as non-alcoholic steatohepatitis (NASH), non-alcoholic fatty liver disease (NAFLD), schizophrenia, bipolar disorder, psychosis, metabolic syndrome, type-2 diabetes, dyslipidaemia, obesity, eating disorders, cardiovascular diseases and disorders, and other conditions as described herein, may be treated. Also included in the present application are certain novel compounds of Formula Ia and pharmaceutical compositions comprising these compounds.