(4-chlorophenyl)(1H-indol-5-yl)methanone | 405275-23-2

• 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: (4-chlorophenyl)(1H-indol-5-yl)methanone
• 英文别名: Methanone,(4-chlorophenyl)-1h-indol-5-yl-；(4-chlorophenyl)-(1H-indol-5-yl)methanone
• CAS: 405275-23-2
• 化学式: C₁₅H₁₀ClNO
• 分子量: 255.703
• InChiKey: KCLSLGMCKDCVHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-chlorophenyl)(1H-indol-5-yl)methanone 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 41.0h， 生成 (+)-5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: Potent and selective aromatase inhibitors

  摘要：

  The synthesis and the aromatase (CYP19) inhibitory activity of 5-[(aryl)(imidazol-1-yl)methyl]-1H-indoles were reported. Among the tested racemate compounds, 5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 8b emerged as a potent CYP19 inhibitor (IC50 = 15.3 nM). Chiral chromatography allowed isolation of the (+) enantiomer 8b2, which was about twice as active as the racemate (IC50 = 9 nM). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.099
• 作为产物：
  描述：

  1-benzenesulfonyl-2,3-dihydro-1H-indole 在 manganese(IV) oxide 、 三氯化铝 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 (4-chlorophenyl)(1H-indol-5-yl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: Potent and selective aromatase inhibitors

  摘要：

  The synthesis and the aromatase (CYP19) inhibitory activity of 5-[(aryl)(imidazol-1-yl)methyl]-1H-indoles were reported. Among the tested racemate compounds, 5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 8b emerged as a potent CYP19 inhibitor (IC50 = 15.3 nM). Chiral chromatography allowed isolation of the (+) enantiomer 8b2, which was about twice as active as the racemate (IC50 = 9 nM). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.099

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。
• Syntheses of 1 <i>H</i> ‐Indoles, Quinolines, and 6‐Membered Aromatic <i>N</i> ‐Heterocycle‐Fused Scaffolds via Palladium(II)‐Catalyzed Aerobic Dehydrogenation under Alkoxide‐Free Conditions
  作者：Hyung‐Seok Yoo、Yo‐Sep Yang、Soo Lim Kim、Seung Hwan Son、Yoon Hu Jang、Jeong‐Won Shin、Nam‐Jung Kim

  DOI：10.1002/asia.202100861

  日期：2021.11.2

  An efficient palladium(II)-catalyzed aerobic dehydrogenation of saturated N-heterocycle-fused scaffolds was developed. This method provides aromatic N-heterocylces including indoles, quinolines, isoquinolines, and other 6-membered N-heterocycles in good to excellent yields without the need of alkoxides (for 48 examples, up to 99% yield).

  开发了一种高效的钯 (II) 催化的饱和N-杂环稠合支架的有氧脱氢反应。该方法无需醇盐即可提供芳香族N-杂环，包括吲哚、喹啉、异喹啉和其他 6 元N-杂环，产率良好至极好（对于 48 个实例，产率高达 99%）。
• Synthesis and biological evaluation of 5-[(aryl)(1H-imidazol-1-yl)methyl]-1H-indoles: Potent and selective aromatase inhibitors
  作者：Marie-Pierre Lézé、Marc Le Borgne、Patricia Pinson、Anja Palusczak、Muriel Duflos、Guillaume Le Baut、Rolf W. Hartmann

  DOI：10.1016/j.bmcl.2005.11.099

  日期：2006.3

  The synthesis and the aromatase (CYP19) inhibitory activity of 5-[(aryl)(imidazol-1-yl)methyl]-1H-indoles were reported. Among the tested racemate compounds, 5-[(4-chlorophenyl)(1H-imidazol-1-yl)methyl]-1H-indole 8b emerged as a potent CYP19 inhibitor (IC50 = 15.3 nM). Chiral chromatography allowed isolation of the (+) enantiomer 8b2, which was about twice as active as the racemate (IC50 = 9 nM). (C) 2005 Elsevier Ltd. All rights reserved.