6-chloro-3-methoxy-1H-indole-2-carboxylic acid ethyl ester | 153501-27-0

• 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: 6-chloro-3-methoxy-1H-indole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 6-chloro-3-methoxyindole-2-carboxylate；Ethyl 6-chloro-3-methoxy-1H-indole-2-carboxylate
• CAS: 153501-27-0
• 化学式: C₁₂H₁₂ClNO₃
• 分子量: 253.685
• InChiKey: DMDBAAZFNMWIKN-UHFFFAOYSA-N

物化性质

• 沸点：
  416.5±40.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-3-methoxy-1H-indole-2-carboxylic acid ethyl ester 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 四丁基溴化铵 、 氨 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 7-chloro-1,2,3,4-tetrahydro-10-methoxypyrazino[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：

  2-氨基-4-氯苯甲酸乙酯 在 ammonium hydroxide 、 sodium 、 sodium carbonate 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 22.5h， 生成 6-chloro-3-methoxy-1H-indole-2-carboxylic acid ethyl ester
  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

• Piperazine derivatives
  申请人：——

  公开号：US20020169163A1

  公开（公告）日：2002-11-14

  Piperazine derivatives, as well as pharmaceutically acceptable salts, solvates and esters thereof, can be used in the form of pharmaceutical preparations for the treatment or prevention of disorders of the central nervous system, damage to the central nervous system, cardiovascular disorders, gastrointestinal disorders, diabetes insipidus, type II diabetes, obesity and sleep apnoea.

  哌嗪衍生物以及其中医药可接受的盐、溶剂合物和酯，可用于制药制剂的形式，用于治疗或预防中枢神经系统疾病、中枢神经系统损伤、心血管疾病、胃肠疾病、尿崩症、2型糖尿病、肥胖和睡眠呼吸暂停。
• 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.
• TETRAHYDRO-PYRAZINO[1,2-A]INDOLES FOR THE TREATMENT OF CENTRAL NERVOUS DISORDERS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1370561B1

  公开（公告）日：2009-02-11
• US6844345B2
  申请人：——

  公开号：US6844345B2

  公开（公告）日：2005-01-18
• [EN] PIPERAZINE DERIVATIVES<br/>[FR] DERIVES DE LA PIPERAZINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002072584A2

  公开（公告）日：2002-09-19

  The present invention refers to chemical compounds of formula (I) as well as pharmaceutically acceptable salts, solvates and esters thereof, wherein R1 to R7 have the significance given in the description and the claims. The compounds can be used in the form of pharmaceutical preparations for the treatment or prevention of disorders of the central nervous system, damage to the central nervous system, cardiovascular disorders, gastrointestinal disorders, diabetes insipidus, type II diabetes, obesity and sleep apnoea.