2-(5-甲氧基-2-甲基-1-(4-(三氟甲基)苯甲酰基)-1H-吲哚-3-基)乙酸 | 806-81-5

• 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
• 中文名称: 2-(5-甲氧基-2-甲基-1-(4-(三氟甲基)苯甲酰基)-1H-吲哚-3-基)乙酸
• 英文名称: 2-(5-methoxy-2-methyl-1-(4-(trifluoromethyl)benzoyl)-1H-indol-3-yl)acetic acid
• 英文别名: 1h-Indole-3-acetic acid,5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]-；2-[5-methoxy-2-methyl-1-[4-(trifluoromethyl)benzoyl]indol-3-yl]acetic acid
• CAS: 806-81-5
• 化学式: C₂₀H₁₆F₃NO₄
• 分子量: 391.347
• InChiKey: WSJYANUXYPFGPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-甲氧基-2-甲基-3-吲哚乙酸 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 trimethyl-tin hydroxide 、 三乙胺 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 2-(5-甲氧基-2-甲基-1-(4-(三氟甲基)苯甲酰基)-1H-吲哚-3-基)乙酸
  参考文献：
  名称：

  Straightforward protocol for the efficient synthesis of varied N1-acylated (aza)indole 2-/3-alkanoic acids and esters: optimization and scale-up

  摘要：

  A library of approximately 40 N-1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2'-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.044

文献信息

• [EN] INDOMETHACIN ANALOGS FOR THE TREATMENT OF CASTRATE-RESISTANT PROSTATE CANCER<br/>[FR] ANALOGUES DE L'INDOMÉTACINE DESTINÉS AU TRAITEMENT DU CANCER DE LA PROSTATE RÉSISTANT À LA CASTRATION
  申请人：UNIV VANDERBILT

  公开号：WO2013059245A1

  公开（公告）日：2013-04-25

  Provided are compositions for inhibiting a biological activity of an aldoketo reductase family 1, member C3 (AKR1 C3) polypeptide. In some embodiments, the compositions are indomethacin derivatives that are AKR1 C3-specific inhibitors. Also provided are methods for producing disclosed indomethacin derivatives that substantially lack cyclooxygenase inhibitory activity but that have AKR1C3 inhibitory activity, methods for inhibiting AKR1C3 polypeptide biological activities, and methods for treating prostate tumors in subjects.

  提供了用于抑制醛酮还原酶家族1成员C3（AKR1 C3）多肽的生物活性的组合物。在某些实施例中，这些组合物是吲哚美酸衍生物，是AKR1 C3特异性抑制剂。还提供了生产所述吲哚美酸衍生物的方法，这些衍生物基本缺乏环氧合酶抑制活性，但具有AKR1C3抑制活性，以及抑制AKR1C3多肽生物活性的方法，以及治疗受试者前列腺肿瘤的方法。
• USEFUL INDOLE COMPOUNDS
  申请人：Bartolini Wilmin

  公开号：US20090264653A1

  公开（公告）日：2009-10-22

  Indoles that have activity as inhibitors of FAAH are described as are indoles and indole derivatives that have activity as inhibitors of DAO.

  本文描述了具有FAAH抑制剂活性的吲哚化合物，以及具有DAO抑制剂活性的吲哚及其衍生物。
• INDOLE COMPOUNDS
  申请人：Talley John Jeffrey

  公开号：US20100197708A1

  公开（公告）日：2010-08-05

  Indole derivatives that are useful for treating pain, inflammation and other conditions are described. Certain of the compounds are benzyl derivatives and others are benzoyl derivatives. The compounds are substituted at least at the 3 position of the indole.

  本文介绍了用于治疗疼痛、炎症和其他疾病的吲哚衍生物。其中某些化合物是苄基衍生物，而其他化合物是苯甲酰基衍生物。这些化合物至少在吲哚的3位被取代。
• INDOMETHACIN ANALOGS FOR THE TREATMENT OF CASTRATE-RESISTANT PROSTATE CANCER
  申请人：Vanderbilt University

  公开号：EP3078374A1

  公开（公告）日：2016-10-12

  Provided are compositions for inhibiting a biological activity of an aldo-keto reductase family 1, member C3 (AKR1C3) polypeptide. In some embodiments, the compositions are indomethacin derivatives that are AKR1C3-specific inhibitors. Also provided are methods for producing disclosed indomethacin derivatives that substantially lack cyclooxygenase inhibitory activity but that have AKR1C3 inhibitory activity, methods for inhibiting AKR1C3 polypeptide biological activities, and methods for treating prostate tumors in subjects.

  本文提供了用于抑制醛酮还原酶家族 1 成员 C3（AKR1C3）多肽生物活性的组合物。在某些实施方案中，这些组合物是 AKR1C3 特异性抑制剂的吲哚美辛衍生物。还提供了生产所公开的基本上缺乏环氧化酶抑制活性但具有AKR1C3抑制活性的吲哚美辛衍生物的方法、抑制AKR1C3多肽生物活性的方法以及治疗受试者前列腺肿瘤的方法。
• Indomethacin analogs for the treatment of castrate-resistant prostate cancer
  申请人：Vanderbilt University

  公开号：US10398678B2

  公开（公告）日：2019-09-03

  Provided are compositions for inhibiting a biological activity of an aldo-keto reductase family 1, member C3 (AKR1C3) polypeptide. In some embodiments, the compositions are indomethacin derivatives that are AKR1C3-specific inhibitors. Also provided are methods for producing disclosed indomethacin derivatives that substantially lack cyclooxygenase inhibitory activity but that have AKR1C3 inhibitory activity, methods for inhibiting AKR1C3 polypeptide biological activities, and methods for treating prostate tumors in subjects.

  本文提供了用于抑制醛酮还原酶家族 1 成员 C3（AKR1C3）多肽生物活性的组合物。在某些实施方案中，这些组合物是 AKR1C3 特异性抑制剂的吲哚美辛衍生物。还提供了生产所公开的基本上缺乏环氧化酶抑制活性但具有AKR1C3抑制活性的吲哚美辛衍生物的方法、抑制AKR1C3多肽生物活性的方法以及治疗受试者前列腺肿瘤的方法。