2-(3-methyl-[1,2,4]oxadiazol-5-yl)-1H-indole | 1239735-68-2

• 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-(3-methyl-[1,2,4]oxadiazol-5-yl)-1H-indole
• 英文别名: 5-(indol-2-yl)-3-methyl-1,2,4-oxadiazole；2-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-indole；5-(1H-indol-2-yl)-3-methyl-1,2,4-oxadiazole
• CAS: 1239735-68-2
• 化学式: C₁₁H₉N₃O
• mdl: MFCD16874954
• 分子量: 199.212
• InChiKey: UBDTXYXAWWOYMO-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122 °C(Solv: ethanol (64-17-5))
• 沸点：
  427.7±37.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  2-(3-methyl-[1,2,4]oxadiazol-5-yl)-1H-indole 、 6-(tert-butoxycarbonylamino-methyl)-3-pyridineboronic acid 在 copper diacetate N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 以17%的产率得到{5-[2-(3-methyl-[1,2,4]oxadiazol-5-yl)-indol-1-yl]-pyridin-2-ylmethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  [EN] INDOLE DERIVATIVES
  [FR] DÉRIVÉS D'INDOLE

  摘要：

  本发明涉及式(I)的吲哒衍生物，其中R1-R6和X在权利要求中定义，并且其光学对映体或消旋体和/或盐是布雷金肽B1的选择性拮抗剂，用于生产这些化合物的方法，含有它们的药物组合物以及它们在治疗或预防疼痛和炎症状况中的使用。

  公开号：

  WO2012059776A1
• 作为产物：
  描述：

  吲哚-2-羧酸甲酯 、 N-羟基乙脒 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以11%的产率得到2-(3-methyl-[1,2,4]oxadiazol-5-yl)-1H-indole
  参考文献：
  名称：

  Design, synthesis and pro-apoptotic antitumour properties of indole-based 3,5-disubstituted oxadiazoles

  摘要：

  A series of new indole-based 3,5-disubstituted 1,2,4-oxadiazoles has been designed and synthesised as potential pro-apoptotic antitumour agents, via the base-catalysed condensation reaction between substituted amidoximes and indole esters. Evaluation of antiproliferative activity against the human cancer cell lines COLO 320 (colorectal) and MIA PACA-2 (pancreatic) revealed IC50 values in the low micromolar range. Selected compounds were able to trigger apoptosis in sensitive cell lines, for example via activation of caspase-3/7, demonstrating that indole-based oxadiazoles possess in vitro antitumour and pro-apoptotic activity. (C) 2010 Elsevier Masson SAS All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.012

文献信息

• [EN] INDOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'INDOLE
  申请人：RICHTER GEDEON NYRT

  公开号：WO2012059776A1

  公开（公告）日：2012-05-10

  The present invention relates to the indole derivatives of formula (I), wherein R1- R6 and X are defined in the claims and optical antipodes or racemates and/or salts thereof which are selective antagonists of bradykinin B1 to process for producing these compounds, pharmacological compositions containing them and to their use in therapy or prevention of painful and inflammatory conditions.

  本发明涉及式(I)的吲哒衍生物，其中R1-R6和X在权利要求中定义，并且其光学对映体或消旋体和/或盐是布雷金肽B1的选择性拮抗剂，用于生产这些化合物的方法，含有它们的药物组合物以及它们在治疗或预防疼痛和炎症状况中的使用。
• INDOLE DERIVATIVES
  申请人：Beke Gyula

  公开号：US20130217702A1

  公开（公告）日：2013-08-22

  The present invention relates to the indole derivatives of formula (I), wherein R 1 -R 6 and X are defined in the claims and optical antipodes or racemates and/or salts thereof which are selective antagonists of bradykinin B1 to process for producing these compounds, pharmacological compositions containing them and to their use in therapy or prevention of painful and inflammatory conditions.

  本发明涉及式(I)的吲哚衍生物，其中R1-R6和X在权利要求中定义，并且其光学对映体或消旋体和/或盐是布雷金肽B1的选择性拮抗剂，用于制备这些化合物的方法，含有它们的药理学组合物以及它们在治疗或预防疼痛和炎症症状中的用途。
• Design, synthesis and pro-apoptotic antitumour properties of indole-based 3,5-disubstituted oxadiazoles
  作者：Noha I. Ziedan、Fabio Stefanelli、Stefano Fogli、Andrew D. Westwell

  DOI：10.1016/j.ejmech.2010.07.012

  日期：2010.10

  A series of new indole-based 3,5-disubstituted 1,2,4-oxadiazoles has been designed and synthesised as potential pro-apoptotic antitumour agents, via the base-catalysed condensation reaction between substituted amidoximes and indole esters. Evaluation of antiproliferative activity against the human cancer cell lines COLO 320 (colorectal) and MIA PACA-2 (pancreatic) revealed IC50 values in the low micromolar range. Selected compounds were able to trigger apoptosis in sensitive cell lines, for example via activation of caspase-3/7, demonstrating that indole-based oxadiazoles possess in vitro antitumour and pro-apoptotic activity. (C) 2010 Elsevier Masson SAS All rights reserved.