1-acetyl-6-trifluoromethyl-5-trifluoromethylsulfonyloxyindoline | 200711-21-3

• 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: 1-acetyl-6-trifluoromethyl-5-trifluoromethylsulfonyloxyindoline
• 英文别名: 1-Acetyl-6-trifluoromethyl-5-trifluoromethylsulphonyloxy-indoline；[1-acetyl-6-(trifluoromethyl)-2,3-dihydroindol-5-yl] trifluoromethanesulfonate
• CAS: 200711-21-3
• 化学式: C₁₂H₉F₆NO₄S
• 分子量: 377.264
• InChiKey: NONUNTMTIOJVRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-acetyl-6-trifluoromethyl-5-trifluoromethylsulfonyloxyindoline 以74的产率得到5-甲基-6-三氟甲基吲哚啉
  参考文献：
  名称：

  Indoline derivatives useful as 5-HT-2C receptor antagonists

  摘要：

  本发明涉及公式（I）的化合物或其盐，其中X为CH或N；R1为氢或C1-6烷基；R2和R3基团独立地为C1-6烷基或三氟甲基，具有药理活性，其制备过程，含有它们的组合物以及它们在治疗中枢神经系统疾病如焦虑症中的应用。

  公开号：

  US06369060B1
• 作为产物：
  描述：

  5-甲氧基-6-(三氟甲基)吲哚啉 在 吡啶 、 碘代三甲硅烷 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 68.0h， 生成 1-acetyl-6-trifluoromethyl-5-trifluoromethylsulfonyloxyindoline
  参考文献：
  名称：

  Biarylcarbamoylindolines Are Novel and Selective 5-HT_2C Receptor Inverse Agonists:  Identification of 5-Methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]- 5-pyridyl]carbamoyl]-6-trifluoromethylindoline (SB-243213) as a Potential Antidepressant/Anxiolytic Agent

  摘要：

  The evolution, synthesis, and biological activity of a novel series of 5-HT2C receptor inverse agonists are reported. Biarylcarbamoylindolines have been identified with excellent 5-HT2C affinity and selectivity over 5-HT2A receptors. In addition, (pyridyloxypyridyl)carbamoylindolines have been discovered with additional selectivity over the closely related 5-HT2B receptor. Compounds from this series are inverse agonists at the human cloned 5-HT2C receptor, completely abolishing basal activity in a functional assay. The new series have reduced P450 inhibitory liability compared to a previously described series of 1-(3-pyridylcarbamoyl)indolines (Bromidge et al. J. Med. Chem. 1998, 41, 1598) from which they evolved. Compounds from this series showed excellent oral activity in a rat mCPP hypolocomotion model and in animal models of anxiety. On the basis of their favorable biological profile, 32 (SB-228357) and 40 (SB-243213) have been selected for further evaluation to determine their therapeutic potential for the treatment of CNS disorders such as depression and anxiety.

  DOI：

  10.1021/jm990388c

文献信息

• [EN] INDOLINE DERIVATIVES USEFUL AS 5-HT-2C RECEPTOR ANTAGONISTS<br/>[FR] DERIVES DE L'INDOLINE UTILES COMME ANTAGONISTES DES RECEPTEURS 5HT-2C
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1997048700A1

  公开（公告）日：1997-12-24

  (EN) The invention relates to heterocyclic compounds of formula (I) or a salt thereof wherein R1 is hydrogen or C1-6 alkyl; R2, R3 and R4 groups are independently hydrogen, halogen or C1-6 alkyl optionally substituted by one or more fluorine atoms, having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of CNS disorders such as anxiety.(FR) L'invention concerne des composés hétérocycliques de formule (I), dans laquelle R1 est hydrogène ou alkyle C1-C6, et les groupes R2, R3 et R4 sont indépendamment hydrogène, halogène ou alkyle C1-C6 éventuellement substitués par un ou plusieurs atomes de fluor, et leurs sels, ces composés ayant une activité pharmacologique. L'invention concerne également des procédés permettant de les préparer et des compositions les contenant, ainsi que leur utilisation dans le traitement des troubles du système nerveux central tels que l'angoisse.

  本发明涉及式（I）的杂环化合物或其盐，其中R1是氢或C1-6烷基；R2、R3和R4基团独立地是氢、卤素或C1-6烷基，可选地被一个或多个氟原子取代，具有药理活性，还涉及其制备方法、含有它们的组合物以及它们在治疗中枢神经系统疾病如焦虑症中的使用。
• INDOLINE DERIVATIVES USEFUL AS 5-HT-2C RECEPTOR ANTAGONISTS
  申请人：SmithKline Beecham plc

  公开号：EP0912554B1

  公开（公告）日：2002-11-27
• INDOLINE DERIVATIVES AS 5HT2C RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0984956A1

  公开（公告）日：2000-03-15
• US6369060B1
  申请人：——

  公开号：US6369060B1

  公开（公告）日：2002-04-09
• US6313145B1
  申请人：——

  公开号：US6313145B1

  公开（公告）日：2001-11-06