6-hydroxy-1,2,3,4-tetrahydro-β-carboline | 38421-97-5

• 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-hydroxy-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 6-hydroxy-1,2,3,4-tetrahydro-β-carboline hydrochloride；2,3,4,9-tetrahydro-1H-beta-carbolin-6-ol hydrochloride；2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-6-ol;hydrochloride
• CAS: 38421-97-5
• 化学式: C₁₁H₁₂N₂O*ClH
• 分子量: 224.69
• InChiKey: WXMLKDUZBWJGOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hydroxy-1,2,3,4-tetrahydro-β-carboline 、 4-苯基苯甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (6-Hydroxy-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)-(4-phenylphenyl)methanone
  参考文献：
  名称：

  Tetrahydro-β-carboline derivatives targeting fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channels

  摘要：

  A series of twenty-five derivatives of tetrahydro-beta-carbolines 1-3 was synthesized and assayed on FAAH and TRPV1 and TRPA1 channels. Four carbamates, that is, 5a,c,e, and 9b inhibited FAAH with significant potency and interacted also effectively with TRPV1 and TRPA1 nociceptive receptors, while ureas 7b,d,f, and 8a,b were endowed with specific submicromolar TRPV1 modulating activities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.137
• 作为产物：
  描述：

  5-羟基色胺盐酸盐 、 聚合甲醛 、 溶剂黄146 以 乙醇 为溶剂， 反应 1.5h， 以to yield 5.9 g of 2,3,4,9-tetrahydro-1H-β-carbolin-6-ol hydrochloride的产率得到6-hydroxy-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  2-(aminomethyl) arylamide analgesics

  摘要：

  本发明揭示了一种2-（氨甲基）芳基酰胺的化学属，其可用作镇痛剂。该属由公式I表示：其中，代表性示例为：

  公开号：

  US07084154B2

文献信息

• EP0520987A4
  申请人：——

  公开号：EP0520987A4

  公开（公告）日：1992-05-13
• US5169852A
  申请人：——

  公开号：US5169852A

  公开（公告）日：1992-12-08
• US7084154B2
  申请人：——

  公开号：US7084154B2

  公开（公告）日：2006-08-01
• [EN] 2-(AMINOMETHYL)ARYLAMIDE ANALGESICS<br/>[FR] ANALGESIQUES A BASE DE 2-(AMINOMETHYL)ARYLAMIDE
  申请人：PHARMACOPEIA DRUG DISCOVERY

  公开号：WO2004071445A2

  公开（公告）日：2004-08-26

  A chemical genus of 2-(aminomethyl)arylamides, which are useful as analgesics, is disclosed. The genus is represented by the Formula I: a representative example is:
• Tetrahydro-β-carboline derivatives targeting fatty acid amide hydrolase (FAAH) and transient receptor potential (TRP) channels
  作者：Giorgio Ortar、Luciano De Petrocellis、Aniello Schiano Moriello、Marco Allarà、Enrico Morera、Marianna Nalli、Vincenzo Di Marzo

  DOI：10.1016/j.bmcl.2012.10.137

  日期：2013.1

  A series of twenty-five derivatives of tetrahydro-beta-carbolines 1-3 was synthesized and assayed on FAAH and TRPV1 and TRPA1 channels. Four carbamates, that is, 5a,c,e, and 9b inhibited FAAH with significant potency and interacted also effectively with TRPV1 and TRPA1 nociceptive receptors, while ureas 7b,d,f, and 8a,b were endowed with specific submicromolar TRPV1 modulating activities. (C) 2012 Elsevier Ltd. All rights reserved.