2-(2-(bromomethyl)-1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetic acid | 1228044-11-8

• 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-(2-(bromomethyl)-1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetic acid
• 英文别名: (2-(Bromomethyl)-1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetic acid；2-[2-(bromomethyl)-1-(4-chlorobenzoyl)-5-methoxyindol-3-yl]acetic acid
• CAS: 1228044-11-8
• 化学式: C₁₉H₁₅BrClNO₄
• 分子量: 436.689
• InChiKey: QEBLVRBBEBJSTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(bromomethyl)-1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetic acid 在 水 、 三氟乙酸 作用下， 生成 2-[2-(hydroxymethyl)-5-methoxy-1-(4-chlorobenzoyl)-1H-indol-3-yl]acetic acid
  参考文献：
  名称：

  Bromination of indomethacin

  摘要：

  Treatment of indomethacin with N-bromosuccinimide in AcOH results in bromination in aromatic positions 4 and 6. while the use of tetrachloromethane allows ultimate bromination at the C(2) Me group of the indole moiety to proceed.

  DOI：

  10.1016/j.mencom.2010.03.016
• 作为产物：
  描述：

  吲哚美辛 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 13.5h， 生成 2-(2-(bromomethyl)-1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl)acetic acid
  参考文献：
  名称：

  SUBSTITUTED 2-(5-HYDROXY-2-METHYL-1H-INDOLE-3-YL)ACETIC ACIDS AND ETHERS THEREOF AND THE USE OF SAME TO TREAT VIRAL DISEASES

  摘要：

  本发明涉及新的取代2-(5-羟基-2-甲基-1H-吲哚-3-基)乙酸，新的抗病毒活性成分，制药组合物，抗病毒药物，以及用于预防和治疗由流感病毒和丙型肝炎病毒（HCV）引起的病毒性疾病的方法。已经披露了新的取代2-(5-羟基-2-甲基-1H-吲哚-3-基)乙酸，其酯具有一般式1和其药用可接受的盐和/或水合物其中：R1代表氨基取代基，可选地取代的C1-C5烷基，酰基或磺酰基；R2和R4独立地代表氢，卤素，可选地取代的C1-C3烷基，可选地取代的羟基，可选地取代的氨基基团，可选地取代的氨甲基，取代的巯基团；R3代表氢，可选地取代的较低C1-C5烷基；R5代表环系统取代基，选择自氢，氟，三氟甲基，羧基，烷氧羰基，可能取代的芳基，杂环烷基，可选地取代的氨甲基，氰基；R6代表羟基取代基，选择自氢，可选地取代的C1-C5烷基，酰基。

  公开号：

  US20110230524A1

文献信息

• Substituted 2-(5-hydroxy-2-methyl-1H-indole-3-yl)acetic acids and ethers thereof and the use of same to treat viral diseases
  申请人：Ivashchenko Andrey Alexandrovich

  公开号：US08481587B2

  公开（公告）日：2013-07-09

  The present invention relates to novel substituted 2-(5-hydroxy-2-methyl-1H-indol-3-yl)acetic acids, to novel antiviral active ingredients, pharmaceutical compositions, antiviral medicaments, methods for prophylaxis and treatment of viral diseases particularly caused by influenza viruses and infectious hepatisis C (HCV) viruses. Novel substituted 2-(5-hydroxy-2-methyl-1H-indol-3-yl)acetic acids, their esters of the general formula 1 and pharmaceutically acceptable salts and/or hydrates thereof have been disclosed wherein: R1 represents amino group substituent selected from hydrogen, optionally substituted C1-C5 alkyl, acyl or sulfonyl; R2 and R4 independently of each other represent alkyl substituent selected from hydrogen, halogen, optionally substituted C1-C3 alkyl, optionally substituted hydroxyl, optionally substituted amino group, optionally substituted aminomethyl, substituted mercapto group; R3 represents hydrogen, optionally substituted lower C1-C5 alkyl; R5 represents cyclic system substituent selected from hydrogen, fluorine, trifluoromethyl, carboxy group, alkyloxycarbonyl, possibly substituted aryl, heterocyclyl, optionally substituted aminomethyl, cyano group; R6 represents hydroxyl group substituent selected from hydrogen, optionally substituted C1-C5 alkyl, acyl.

  本发明涉及新型取代的2-(5-羟基-2-甲基-1H-吲哚-3-基)乙酸，新型抗病毒活性成分，制药组合物，抗病毒药物，以及用于预防和治疗病毒疾病，尤其是由流感病毒和传染性肝炎C（HCV）病毒引起的病毒疾病的方法。 已经披露了新型取代的2-(5-羟基-2-甲基-1H-吲哚-3-基)乙酸，它们的酯类具有通式1，并且它们的药学上可接受的盐和/或水合物，其中：R1代表氨基基团取代物，选自氢、可选取代的C1-C5烷基、酰基或磺酰基；R2和R4独立地代表烷基取代物，选自氢、卤素、可选取代的C1-C3烷基、可选取代的羟基、可选取代的氨基基团、可选取代的氨甲基、取代的硫醇基；R3代表氢、可选取代的较低的C1-C5烷基；R5代表环状系统取代物，选自氢、氟、三氟甲基、羧基、烷氧羰基、可能取代的芳基、杂环基、可选取代的氨甲基、氰基；R6代表羟基基团取代物，选自氢、可选取代的C1-C5烷基、酰基。
• US8481587B2
  申请人：——

  公开号：US8481587B2

  公开（公告）日：2013-07-09
• SUBSTITUTED 2-(5-HYDROXY-2-METHYL-1H-INDOLE-3-YL)ACETIC ACIDS AND ETHERS THEREOF AND THE USE OF SAME TO TREAT VIRAL DISEASES
  申请人：Ivashchenko Andrey Alexandrovich

  公开号：US20110230524A1

  公开（公告）日：2011-09-22

  The present invention relates to novel substituted 2-(5-hydroxy-2-methyl-1H-indol-3-yl)acetic acids, to novel antiviral active ingredients, pharmaceutical compositions, antiviral medicaments, methods for prophylaxis and treatment of viral diseases particularly caused by influenza viruses and infectious hepatisis C (HCV) viruses. Novel substituted 2-(5-hydroxy-2-methyl-1H-indol-3-yl)acetic acids, their esters of the general formula 1 and pharmaceutically acceptable salts and/or hydrates thereof have been disclosed wherein: R 1 represents amino group substituent selected from hydrogen, optionally substituted C 1 -C 5 alkyl, acyl or sulfonyl; R 2 and R 4 independently of each other represent alkyl substituent selected from hydrogen, halogen, optionally substituted C 1 -C 3 alkyl, optionally substituted hydroxyl, optionally substituted amino group, optionally substituted aminomethyl, substituted mercapto group; R 3 represents hydrogen, optionally substituted lower C 1 -C 5 alkyl; R 5 represents cyclic system substituent selected from hydrogen, fluorine, trifluoromethyl, carboxy group, alkyloxycarbonyl, possibly substituted aryl, heterocyclyl, optionally substituted aminomethyl, cyano group; R 6 represents hydroxyl group substituent selected from hydrogen, optionally substituted C 1 -C 5 alkyl, acyl.

  本发明涉及新的取代2-(5-羟基-2-甲基-1H-吲哚-3-基)乙酸，新的抗病毒活性成分，制药组合物，抗病毒药物，以及用于预防和治疗由流感病毒和丙型肝炎病毒（HCV）引起的病毒性疾病的方法。已经披露了新的取代2-(5-羟基-2-甲基-1H-吲哚-3-基)乙酸，其酯具有一般式1和其药用可接受的盐和/或水合物其中：R1代表氨基取代基，可选地取代的C1-C5烷基，酰基或磺酰基；R2和R4独立地代表氢，卤素，可选地取代的C1-C3烷基，可选地取代的羟基，可选地取代的氨基基团，可选地取代的氨甲基，取代的巯基团；R3代表氢，可选地取代的较低C1-C5烷基；R5代表环系统取代基，选择自氢，氟，三氟甲基，羧基，烷氧羰基，可能取代的芳基，杂环烷基，可选地取代的氨甲基，氰基；R6代表羟基取代基，选择自氢，可选地取代的C1-C5烷基，酰基。
• Bromination of indomethacin
  作者：Alexandre V. Ivachtchenko、Pavel M. Yamanushkin、Oleg D. Mitkin、Oleg I. Kiselev

  DOI：10.1016/j.mencom.2010.03.016

  日期：2010.3

  Treatment of indomethacin with N-bromosuccinimide in AcOH results in bromination in aromatic positions 4 and 6. while the use of tetrachloromethane allows ultimate bromination at the C(2) Me group of the indole moiety to proceed.