6-氯-3-羟基-1H-吲哚-2-羧酸乙基酯 | 153501-26-9

• 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: 6-氯-3-羟基-1H-吲哚-2-羧酸乙基酯
• 英文名称: ethyl 6-chloro-3-hydroxyindole-2-carboxylate
• 英文别名: Ethyl 6-chloro-3-hydroxy-1H-indole-2-carboxylate
• CAS: 153501-26-9
• 化学式: C₁₁H₁₀ClNO₃
• 分子量: 239.658
• InChiKey: FLSIBDXQAOHFCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  6-氯-3-羟基-1H-吲哚-2-羧酸乙基酯 在 sodium hydroxide 、 四丁基溴化铵 、 氨 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 36.5h， 生成 7-chloro-1,2,3,4-tetrahydro-10-methoxypyrazino[1,2-a]indol-1-one
  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：

  2-氨基-4-氯苯甲酸乙酯 在 ammonium hydroxide 、 sodium 、 sodium carbonate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 22.0h， 生成 6-氯-3-羟基-1H-吲哚-2-羧酸乙基酯
  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

• Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARγ partial agonists
  作者：James F. Dropinski、Taro Akiyama、Monica Einstein、Bahanu Habulihaz、Tom Doebber、Joel P. Berger、Peter T. Meinke、Guo Q. Shi

  DOI：10.1016/j.bmcl.2005.08.002

  日期：2005.11

  A series of novel aryl indole-2-carboxylic acids has been identified as potent selective PPAR gamma modulators. Their chemical synthesis and in vitro activities are discussed. Compound 5 was selected for in vivo testing in the db/db mouse model of type 2 diabetes and resulted in reduction of hyperglycemia at comparable plasma exposure when compared to rosiglitazone. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.