1-(4-chlorophenyl)-2-(toluene-4-sulfonyl)-1,2,3,5-tetrahydropyrido[4,3-b]indol-4-one | 568589-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-chlorophenyl)-2-(toluene-4-sulfonyl)-1,2,3,5-tetrahydropyrido[4,3-b]indol-4-one
• 英文别名: 1-(4-chlorophenyl)-2-(4-methylphenyl)sulfonyl-3,5-dihydro-1H-pyrido[4,3-b]indol-4-one
• CAS: 568589-01-5
• 化学式: C₂₄H₁₉ClN₂O₃S
• 分子量: 450.945
• InChiKey: LVOSNGZYFBXGHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-2-(toluene-4-sulfonyl)-1,2,3,5-tetrahydropyrido[4,3-b]indol-4-one 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1-(4-chlorophenyl)-5H-pyrido[4,3-b]indol-4-ol
  参考文献：
  名称：

  Syntheses of Functionalized 1,4-Disubstituted γ-Carbolines

  摘要：

  We report the complete synthesis of a variety of 1,4-disubstituted gamma-carbolines. These compounds are of particular interest for their involvement in many biological processes and are believed to possess various medicinal activities. A large number of N-tosylaldimines were condensed with indoles affording an array of 3-aminomethyl indoles. Subsequent additions, followed by intramolecular cyclization, afforded an array of 1,2-dihydro-3H-gamma-carbolones in good yield. Upon subsequent aromatization, the corresponding fully aromatic functionalized 1-aryl-4-hydroxy-gamma-carbolines resulted.

  DOI：

  10.1021/jo034290o
• 作为产物：
  描述：

  3-bromo-1-(tert-butyldimethylsilyl)indole 在 Bentonite K-10 clay 、 叔丁基锂 、 sodium ethanolate 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 39.75h， 生成 1-(4-chlorophenyl)-2-(toluene-4-sulfonyl)-1,2,3,5-tetrahydropyrido[4,3-b]indol-4-one
  参考文献：
  名称：

  Syntheses of Functionalized 1,4-Disubstituted γ-Carbolines

  摘要：

  We report the complete synthesis of a variety of 1,4-disubstituted gamma-carbolines. These compounds are of particular interest for their involvement in many biological processes and are believed to possess various medicinal activities. A large number of N-tosylaldimines were condensed with indoles affording an array of 3-aminomethyl indoles. Subsequent additions, followed by intramolecular cyclization, afforded an array of 1,2-dihydro-3H-gamma-carbolones in good yield. Upon subsequent aromatization, the corresponding fully aromatic functionalized 1-aryl-4-hydroxy-gamma-carbolines resulted.

  DOI：

  10.1021/jo034290o

文献信息

• Synthesized gamma-carbolines
  申请人：Wynne H. James

  公开号：US20050131010A1

  公开（公告）日：2005-06-16

  The present invention concerns the compounds of the formula: and the prodrug and salts thereof, wherein R may be a hydroxyl or other pendent group and Ar is an aryl. The compositions may be adapted for the treatment of neurodegenerative diseases. Further, the compositions may be adapted as a pharmaceutical such as an antipsychotic pharmaceutical, an antibiotic pharmaceutical, an antiviral pharmaceutical or an antitumor pharmaceutical.

  本发明涉及式中的化合物： 及其原药和盐类，其中 R 可以是羟基或其他悬垂基团，Ar 是芳基。这些组合物可用于治疗神经退行性疾病。此外，这些组合物还可用作药物，如抗精神病药物、抗生素药物、抗病毒药物或抗肿瘤药物。
• US6872830B1
  申请人：——

  公开号：US6872830B1

  公开（公告）日：2005-03-29
• US7060830B2
  申请人：——

  公开号：US7060830B2

  公开（公告）日：2006-06-13
• Syntheses of Functionalized 1,4-Disubstituted γ-Carbolines
  作者：James H. Wynne、Wayne M. Stalick

  DOI：10.1021/jo034290o

  日期：2003.6.1

  We report the complete synthesis of a variety of 1,4-disubstituted gamma-carbolines. These compounds are of particular interest for their involvement in many biological processes and are believed to possess various medicinal activities. A large number of N-tosylaldimines were condensed with indoles affording an array of 3-aminomethyl indoles. Subsequent additions, followed by intramolecular cyclization, afforded an array of 1,2-dihydro-3H-gamma-carbolones in good yield. Upon subsequent aromatization, the corresponding fully aromatic functionalized 1-aryl-4-hydroxy-gamma-carbolines resulted.