methyl 3-(1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl)propanoate | 1412449-49-0

• 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: methyl 3-(1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl)propanoate
• 英文别名: methyl 3-[1-(4-chlorobenzoyl)-5-fluoro-2-methylindol-3-yl]propanoate
• CAS: 1412449-49-0
• 化学式: C₂₀H₁₇ClFNO₃
• 分子量: 373.811
• InChiKey: STEULQJWPASECX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.2
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl)propanoate 在 trimethyl-tin hydroxide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以95%的产率得到3-(1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl)propanoic acid
  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
• 作为产物：
  描述：

  4-氧代己酸 在 硫酸 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 0.59h， 生成 methyl 3-(1-(4-chlorobenzoyl)-5-fluoro-2-methyl-1H-indol-3-yl)propanoate
  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。
• INDOMETHACIN ANALOGS FOR THE TREATMENT OF CASTRATE-RESISTANT PROSTATE CANCER
  申请人：Vanderbilt University

  公开号：US20140371261A1

  公开（公告）日：2014-12-18

  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.

  提供了一些用于抑制醛酮还原酶家族1成员C3（AKR1 C3）多肽生物活性的组合物。在某些实施例中，这些组合物是AKR1 C3特异性抑制剂的吲哚美辛衍生物。还提供了制备所述吲哚美辛衍生物的方法，这些方法基本上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和治疗受试者的前列腺肿瘤的方法。
• Indomethacin analogs for the treatment of castrate-resistant prostate cancer
  申请人：Vanderbilt University

  公开号：US09346803B2

  公开（公告）日：2016-05-24

  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AKR1 C3特异性抑制剂的靛烷酸衍生物。还提供了制备所述靛烷酸衍生物的方法，这些方法基本上缺乏环氧合酶抑制活性，但具有AKR1C3抑制活性，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。
• US9346803B2
  申请人：——

  公开号：US9346803B2

  公开（公告）日：2016-05-24
• US9895351B2
  申请人：——

  公开号：US9895351B2

  公开（公告）日：2018-02-20