5-bromo-1-ethyl-2-(4-fluorobenzoyl)-3-methyl-1H-indole | 222306-38-9

• 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: 5-bromo-1-ethyl-2-(4-fluorobenzoyl)-3-methyl-1H-indole
• 英文别名: (5-Bromo-1-ethyl-3-methylindol-2-yl)-(4-fluorophenyl)methanone
• CAS: 222306-38-9
• 化学式: C₁₈H₁₅BrFNO
• 分子量: 360.226
• InChiKey: WHRCNKDAUHNKII-UHFFFAOYSA-N

物化性质

• 沸点：
  459.8±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-1-ethyl-2-(4-fluorobenzoyl)-3-methyl-1H-indole 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-Bromo-1-ethyl-2-[(4-fluoro-phenyl)-imidazol-1-yl-methyl]-3-methyl-1H-indole
  参考文献：
  名称：

  New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2,3 or 5-(α-azolylbenzyl)-1H-indoles

  摘要：

  Six azolyl substituted indoles were synthesized and tested for their activity to inhibit two P450 enzymes: P450 arom and P450 17 alpha. It was observed that the introduction of alpha-imidazolylbenzyl chain at carbon 3 or 5 on indole nucleus led to very active molecules. Compounds 22, 23 and especially 33 demonstrate very high potential against P450 arom. Under our assay conditions of high substrate concentration the IC50 are 0.057, 0.0785 and 0.041 mu M,respectively. These compounds are moderate inhibitors against P450 17 alpha. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00737-9
• 作为产物：
  描述：

  5-溴吲哚-3-甲醛 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-bromo-1-ethyl-2-(4-fluorobenzoyl)-3-methyl-1H-indole
  参考文献：
  名称：

  New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2,3 or 5-(α-azolylbenzyl)-1H-indoles

  摘要：

  Six azolyl substituted indoles were synthesized and tested for their activity to inhibit two P450 enzymes: P450 arom and P450 17 alpha. It was observed that the introduction of alpha-imidazolylbenzyl chain at carbon 3 or 5 on indole nucleus led to very active molecules. Compounds 22, 23 and especially 33 demonstrate very high potential against P450 arom. Under our assay conditions of high substrate concentration the IC50 are 0.057, 0.0785 and 0.041 mu M,respectively. These compounds are moderate inhibitors against P450 17 alpha. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00737-9

文献信息

• Antifungal and/or antiparasitic pharmaceutical composition and novel indole derivatives as active principle of such a composition
  申请人：——

  公开号：US20040067998A1

  公开（公告）日：2004-04-08

  The present invention relates to novel indole derivatives, their method of preparation and their pharmacological activity as antimycotic and/or antiparasitic compounds.

  这项发明涉及新型吲哚衍生物，它们的制备方法以及它们作为抗真菌和/或抗寄生虫化合物的药理活性。
• New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2,3 or 5-(α-azolylbenzyl)-1H-indoles
  作者：Marc Le Borgne、Pascal Marchand、Bénédicte Delevoye-Seiller、Jean-Michel Robert、Guillaume Le Baut、Rolf W. Hartmann、Martina Palzer

  DOI：10.1016/s0960-894x(98)00737-9

  日期：1999.2

  Six azolyl substituted indoles were synthesized and tested for their activity to inhibit two P450 enzymes: P450 arom and P450 17 alpha. It was observed that the introduction of alpha-imidazolylbenzyl chain at carbon 3 or 5 on indole nucleus led to very active molecules. Compounds 22, 23 and especially 33 demonstrate very high potential against P450 arom. Under our assay conditions of high substrate concentration the IC50 are 0.057, 0.0785 and 0.041 mu M,respectively. These compounds are moderate inhibitors against P450 17 alpha. (C) 1999 Elsevier Science Ltd. All rights reserved.