2-(1,2-dihydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile | 868692-84-6

• 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-(1,2-dihydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile
• 英文别名: 2-(1,2-dihydroxypropan-2-yl)-6-(trifluoromethyl)-1H-indole-5-carbonitrile
• CAS: 868692-84-6
• 化学式: C₁₃H₁₁F₃N₂O₂
• 分子量: 284.238
• InChiKey: GWWASNRIYXATED-UHFFFAOYSA-N

物化性质

• 沸点：
  520.4±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  80
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(1,2-dihydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile 、 对氟苯腈 在 sodium hydride 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 0.5h， 生成 2-[2-(4-Cyano-phenoxy)-1-hydroxy-1-methyl-ethyl]-6-trifluoromethyl-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Novel indole derivatives as selective androgen receptor modulators (SARMS)

  摘要：

  本发明涉及新型吲哚衍生物，含有它们的药物组合物以及它们在治疗由雄激素受体调节的疾病和症状中的应用。

  公开号：

  US20050245485A1
• 作为产物：
  描述：

  4-氨基-2-三氟甲基苯甲腈 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(1,2-dihydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile
  参考文献：
  名称：

  A bioisosteric approach to the discovery of indole carbinol androgen receptor ligands

  摘要：

  Two potential bioisosteres of the nonsteroidal antiandrogen bicalutamide, an imidazolidinone and an indole, were synthesized and tested for their androgen receptor binding. Indole was discovered to be a suitable bioisostere for the acyl anilide moiety in the parent compound. Several analogs in the indole series were found to be 10-fold better than bicalutamide in binding to the recombinant androgen receptor binding domain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.036

文献信息

• Novel indole derivatives as selective androgen receptor modulator (SARMS)
  申请人：Lanter C. James

  公开号：US20050250740A1

  公开（公告）日：2005-11-10

  The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.

  本发明涉及新型吲哚衍生物，含有它们的药物组合物以及它们在治疗由雄激素受体调节的疾病和症状中的应用。
• NOVEL INDOLE DERIVATIVES AS SELECTIVE ANDROGEN RECEPTOR MODULATORS (SARMS)
  申请人：Lanter James C.

  公开号：US20090216023A1

  公开（公告）日：2009-08-27

  The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.

  本发明涉及新型吲哚衍生物，包含它们的药物组合物以及它们在治疗由雄激素受体调节的疾病和症状中的应用。
• Indole derivatives as selective androgen receptor modulators (SARMS)
  申请人：Janssen Pharmaceutica N.V.

  公开号：US07282507B2

  公开（公告）日：2007-10-16

  The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.

  本发明涉及新颖的吲哚衍生物、包含它们的药物组合物以及它们在治疗由雄激素受体调节的疾病和症状中的应用。
• Indole derivatives as selective androgen receptor modulator (SARMS)
  申请人：Janssen Pharmaceutica N.V.

  公开号：US07288553B2

  公开（公告）日：2007-10-30

  The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.

  本发明涉及一种新型吲哚衍生物，包含它们的制药组合物以及它们在治疗受雄激素受体调节的疾病和病症中的应用。
• Indole derivatives as selective androgen receptor modulators (sarms)
  申请人：Janssen Pharmaceutica N.V.

  公开号：EP2078712A1

  公开（公告）日：2009-07-15

  The present invention is directed to novel indole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.

  本发明涉及新型吲哚衍生物、含有这些衍生物的药物组合物及其在治疗受雄激素受体调节的紊乱和病症中的用途。