4-bromo-3-methoxyindole-2-carboxylic acid | 190433-52-4

• 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: 4-bromo-3-methoxyindole-2-carboxylic acid
• 英文别名: 4-bromo-3-methoxy-1H-indole-2-carboxylic Acid
• CAS: 190433-52-4
• 化学式: C₁₀H₈BrNO₃
• 分子量: 270.082
• InChiKey: WMDBLBZGJOYYIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-3-methoxyindole-2-carboxylic acid 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 四丁基溴化铵 、 氨 、 氢气 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 39.0h， 生成 1,2,3,4-tetrahydro-10-methoxy-9-isopropylpyrazino[1,2-a]indole
  参考文献：
  名称：

  Synthesis, pharmacology and therapeutic potential of 10-methoxypyrazino[1,2-a]indoles, partial agonists at the 5HT2C receptor

  摘要：

  A series of new 10-methoxypyrazino[1,2-a]indoles has been prepared and shown to be 5HT(2C) receptor ligands. The studied compounds 10a-j were found to act as partial agonists at the 5HT(2C) receptor, binding with high affinity and moderate selectivity versus 5HT(1A) and 5HT(2A) receptors, but inducing only a submaximal increase in phosphoinositol formation. Compound 10j was demonstrated to be active in animal models of obsessive-compulsive disorder, depression and panic anxiety.

  DOI：

  10.1016/s0223-5234(97)83976-1
• 作为产物：
  描述：

  ethyl 4-bromo-3-methoxyindole-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以86%的产率得到4-bromo-3-methoxyindole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis, pharmacology and therapeutic potential of 10-methoxypyrazino[1,2-a]indoles, partial agonists at the 5HT2C receptor

  摘要：

  A series of new 10-methoxypyrazino[1,2-a]indoles has been prepared and shown to be 5HT(2C) receptor ligands. The studied compounds 10a-j were found to act as partial agonists at the 5HT(2C) receptor, binding with high affinity and moderate selectivity versus 5HT(1A) and 5HT(2A) receptors, but inducing only a submaximal increase in phosphoinositol formation. Compound 10j was demonstrated to be active in animal models of obsessive-compulsive disorder, depression and panic anxiety.

  DOI：

  10.1016/s0223-5234(97)83976-1

文献信息

• SPIRO-PIPERIDINE DERIVATIVES
  申请人：Bissantz Caterina

  公开号：US20080139553A1

  公开（公告）日：2008-06-12

  The present invention is concerned with novel indol-2-yl-carbonyl-spiro-piperidine derivatives as V1 a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use for the treatment of anxiety, depressive disorders and other diseases. The compounds of present invention are represented by the general formula (I) wherein R 1 to R 1 , X and Y are as defined in the specification.

  本发明涉及作为V1a受体拮抗剂的新型吲哚-2-基-羰基-螺环哌啶衍生物，其制备方法，含有它们的药物组合物以及它们用于治疗焦虑、抑郁症和其他疾病的用途。本发明的化合物由通式（I）表示，其中R1至R1、X和Y如规范中所定义。
• SPIRO-PIPERIDINE DERIVATIVES AS VIA RECEPTOR ANTAGONISTS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP2102207B1

  公开（公告）日：2010-06-02
• US8202993B2
  申请人：——

  公开号：US8202993B2

  公开（公告）日：2012-06-19
• [EN] SPIRO-PIPERIDINE DERIVATIVES AS VIA RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS DE SPIRO-PIPÉRIDINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2008068185A1

  公开（公告）日：2008-06-12

  [EN] The present invention is concerned with novel indol-2-yl-carbonyl-spiro-piperidine derivatives as VIa receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments. The active compounds of the present invention are useful in the prevention and/or treatment of anxiety and depressive disorders and other diseases. The compounds of present invention are represented by the general formula (I) wherein R¹ to R¹, X and Y are as defined in the specification.
  [FR] Cette invention concerne des dérivés d'indol-2-yl-carbonyl-pipéridine en tant qu'antagonistes du récepteur V1a, leur fabrication, des compositions pharmaceutiques les renfermant et leurs utilisations en tant que médicaments. Les composés actifs de l'invention conviennent pour la prévention et/ou le traitement de l'angoisse et des troubles à caractère dépressif et autres pathologies. Les composés de cette invention sont représentés par la formule générale (I) dans laquelle R¹ à R¹, X et Y sont comme définis dans le descriptif.
• Synthesis, pharmacology and therapeutic potential of 10-methoxypyrazino[1,2-a]indoles, partial agonists at the 5HT2C receptor
  作者：M Bös、F Jenck、JR Martin、JL Moreau、V Mutel、AJ Sleight、U Widmer

  DOI：10.1016/s0223-5234(97)83976-1

  日期：1997.1

  A series of new 10-methoxypyrazino[1,2-a]indoles has been prepared and shown to be 5HT(2C) receptor ligands. The studied compounds 10a-j were found to act as partial agonists at the 5HT(2C) receptor, binding with high affinity and moderate selectivity versus 5HT(1A) and 5HT(2A) receptors, but inducing only a submaximal increase in phosphoinositol formation. Compound 10j was demonstrated to be active in animal models of obsessive-compulsive disorder, depression and panic anxiety.