2-(2-oxobenzopyran-3-yl)indole | 108160-46-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2-(2-oxobenzopyran-3-yl)indole
• 英文别名: 3-(indol-2-yl)coumarin；3-(1H-indol-2-yl)-chromen-2-one；benzazolyl-coumarin；3-indolylchromone；3-Indolyl-coumarin；3-(1H-indol-2-yl)chromen-2-one
• CAS: 108160-46-9
• 化学式: C₁₇H₁₁NO₂
• 分子量: 261.28
• InChiKey: ISTIXAKUPNGALF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-oxobenzopyran-3-yl)indole 在 硫酸 、 三氯氧磷 作用下， 生成 2-chloro-N'-((2-(2-oxo-2H-chromen-3-yl)-1H-indol-3-yl)methylene)benzohydrazide
  参考文献：
  名称：

  Kamath, Pooja R.; Sunil, Dhanya; Ajees, A. Abdul, European Journal of Medicinal Chemistry, 2016, vol. 120, p. 134 - 147

  摘要：

  DOI：
• 作为产物：
  描述：

  3-乙酰基香豆素 在 甲烷磺酸 、 四磷十氧化物 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-(2-oxobenzopyran-3-yl)indole
  参考文献：
  名称：

  Kamath, Pooja R.; Sunil, Dhanya; Ajees, A. Abdul, European Journal of Medicinal Chemistry, 2016, vol. 120, p. 134 - 147

  摘要：

  DOI：

文献信息

• Chromone derivative, process for preparing same and pharmaceutical composition
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP0758649A1

  公开（公告）日：1997-02-19

  A chromone derivative of the formula (I): wherein R11 is a pyrazolyl, pyrrolyl, triazolyl, benzotriazolyl, benzimidazolyl, indazolyl, or indolyl group, R2, R3, R4, and R5 is independently a hydrogen or halogen atom, or a hydroxy or alkoxy group, or an alkoxy group substituted with one or more alkoxy groups, and X is an oxygen or sulfur atom, or a salt thereof is disclosed. The chromone derivative inhibits the activity of matrix metalloproteinase.

  一种式(I)的铬酮衍生物： 其中 R11 是吡唑基、吡咯基、三唑基、苯并三唑基、苯并咪唑基、吲唑基或吲哚基，R2、R3、R4 和 R5 独立地是氢原子或卤素原子，或羟基或烷氧基，或被一个或多个烷氧基取代的烷氧基，X 是氧原子或硫原子，或其盐。铬酮衍生物可抑制基质金属蛋白酶的活性。
• Rao, Laxmi; Mukerjee, Arya K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 2, p. 166 - 167
  作者：Rao, Laxmi、Mukerjee, Arya K.

  DOI：——

  日期：——
• Sinnur, K. H.; Siddappa, S.; Hiremath, Shivayogi P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 894 - 896
  作者：Sinnur, K. H.、Siddappa, S.、Hiremath, Shivayogi P.、Purohit, Muralidhar G.

  DOI：——

  日期：——
• Some new indole–coumarin hybrids; Synthesis, anticancer and Bcl-2 docking studies
  作者：Pooja R. Kamath、Dhanya Sunil、A. Abdul Ajees、K.S.R. Pai、Shubhankar Das

  DOI：10.1016/j.bioorg.2015.10.001

  日期：2015.12

  Hybrid molecules have attracted attention for their improved biological activity, selectivity and lesser side effects profile, distinct from their individual components. In the quest for novel anticancer drug entities, three series of indole-coumarin hybrids - 3-(1-benzyl-1H-indol-2-yl)-2H-chromen-2-ones, 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehydes and 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carboxylic acids were synthesized. All the synthesized compounds were characterized by spectral techniques like IR, H-1 NMR, C-13 NMR, mass spectrometry and elemental analysis. In silico docking studies of synthesized molecules with apoptosis related gene Bcl-2 that is recognized to play an important role in tumerogenesis were carried out. Dose-dependent cytotoxic effect of the compounds in human breast adenocarcinoma (MCF-7) and normal cell lines were assessed using MTT assay and compared with that of the standard marketed drug, Vincristine. Compound 4c had a highly lipophilic bromine substituent capable of forming halogen bond and was identified as a potent molecule both in docking as well as cytotoxicity studies. Flow cytometric cell cycle analysis of 4c exhibited apoptotic mode of cell death due to cell cycle arrest in G2/M phase. Structure activity relationship of these hybrid molecules was also studied to determine the effect of steric and electronic properties of the substituents on cell viability. (C) 2015 Elsevier Inc. All rights reserved.
• Rao Laxmi, Mukerjee Arya K., Indian J. Chem. B, 33 (1994) N 2, S 166-167
  作者：Rao Laxmi, Mukerjee Arya K.

  DOI：——

  日期：——