2,3,4,9-四氢-1H-咔唑-2-胺 | 72898-07-8

• 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: 2,3,4,9-四氢-1H-咔唑-2-胺
• 英文名称: 2,3,4,9-tetrahydro-1H-carbazol-2-amine
• 英文别名: (2RS)-2,3,4,9-tetrahydro-1H-2-carbazolamine；2,3 4,9-tetrahydro-1H-carbazol-2-ylamine
• CAS: 72898-07-8
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: DEBNIKRHYDWHIG-UHFFFAOYSA-N

物化性质

• 沸点：
  362.5±42.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 储存条件：
  储存条件：2-8°C，密封，干燥。

反应信息

• 作为反应物：
  描述：

  2,3,4,9-四氢-1H-咔唑-2-胺 在 formamide 作用下， 生成 N-(1,3,4,9-tetrahydro-2H-carbazol-2-yl)formamide
  参考文献：
  名称：

  Antidepressant 2-amino- and -2-(substituted

  摘要：

  用于缓解哺乳动物的抑郁症或作为中间化合物的2-氨基和2-(取代氨基)-四氢和-顺式六氢-咔唑醇。

  公开号：

  US04254134A1
• 作为产物：
  描述：

  (Z)-3,4-dihydro-1H-carbazol-2(9H)-one oxime 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以22.66%的产率得到2,3,4,9-四氢-1H-咔唑-2-胺
  参考文献：
  名称：

  Discovery of tetrahydrocarbazoles as dual pERK and pRb inhibitors

  摘要：

  The extracellular signal-regulated kinase (ERK) is one of the most important molecular targets for cancer that controls diverse cellular processes such as proliferation, survival, differentiation and motility. Similarly, the Rb (retinoblastoma protein) is a tumor suppressor protein and its function is to prevent excessive cell growth by inhibiting cell cycle progression. When the cell is ready to divide, pRb is phosphorylated, becomes inactive and allows cell cycle progression. Herein, we discovered a new series of tetrahydrocarbazoles as dual inhibitors of pERK and pRb phosphorylation. The in-house small molecule library was screened for inhibition of pERK and pRb phosphorylation, which led to the discovery of tetrahydrocarbazole series of compounds as potential leads. N-(3-methylcyclopenty1)-6-nitro-2,3,4,4a,9,9a-hexahydro-1H-carbazol-2-amine (1) is the dual inhibitor lead identified through screening, displaying inhibition of PERK and pRb phosphorylation with IC50 values of 5.5 and 4.8 mu M, respectively. A short structure-activity relationship (SAR) study has been performed, which identified another dual inhibitor 9-methyl-N-(4-methylbenzy1)-2,3,4,4a,9,9a-hexahydro-1H-carbazol-2-amine (16) with IC50 values 4.4 and 3.5 mu M for inhibition of pERK and pRb phosphorylation, respectively. This compound has a potential for further lead optimization to discover promising molecularly-targeted anticancer agents. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.062

文献信息

• Antidepressant 2-amino-and-2-(substituted
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04343812A1

  公开（公告）日：1982-08-10

  2-Amino- and 2-(substituted amino)-tetrahydro- and -cis-hexahydro-carbazoles useful for alleviating depression in mammals or as intermediate compounds thereto.

  2-氨基和2-(取代氨基)-四氢和-顺式六氢-咔唑可用于缓解哺乳动物的抑郁症状，或作为其中间化合物。
• Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives
  申请人：Sabb Louise Annmarie

  公开号：US20060205759A1

  公开（公告）日：2006-09-14

  The present invention provides cycloalkylfused indole, benzothiophene, benzofuran, and indene derivatives, and methods for using them to, for example, treat, prevent and/or ameliorate central nervous system diseases by antagonizing 5-HT 1A receptors and modulating serotonin levels.

  本发明提供环烷基融合吲哚、苯并噻吩、苯并呋喃和茚烯衍生物，以及使用它们的方法，例如通过拮抗5-HT1A受体和调节血清素水平来治疗、预防和/或改善中枢神经系统疾病。
• CYCLOALKYLFUSED INDOLE, BENZOTHIOPHENE, BENZOFURAN AND INDENE DERIVATIVES
  申请人：Sabb Louise Annmarie

  公开号：US20080081910A1

  公开（公告）日：2008-04-03

  The present invention provides cycloalkylfused indole, benzothiophene, benzofuran, and indene derivatives, and methods for using them to, for example, treat, prevent and/or ameliorate central nervous system diseases by antagonizing 5-HT 1A receptors and modulating serotonin levels.

  本发明提供了环烷基融合吲哚、苯并噻吩、苯并呋喃和茚烯衍生物，以及使用它们的方法，例如通过拮抗5-HT1A受体和调节血清素水平来治疗、预防和/或改善中枢神经系统疾病。
• Cycloalkyfused indole, benzothiophene, benzofuran and idene derivatives
  申请人：Wyeth

  公开号：US07297704B2

  公开（公告）日：2007-11-20

  The present invention provides cycloalkylfused indole, benzothiophene, benzofuran, and indene derivatives, and methods for using them to, for example, treat, prevent and/or ameliorate central nervous system diseases by antagonizing 5-HT1A receptors and modulating serotonin levels.

  本发明提供了环状烷基融合的吲哚、苯并噻吩、苯并呋喃和茚烯衍生物，以及使用它们的方法，例如通过拮抗5-HT1A受体和调节血清素水平来治疗、预防和/或改善中枢神经系统疾病。
• Carbazoles, process for their preparation, pharmaceutical compositions containing them, and intermediates thereto
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0004342A1

  公开（公告）日：1979-10-03

  2-Amino- and 2-(substituted amino)-tetrahydro- and -cis-hexahydro-carbazoles, useful for alleviating depression in mammals and intermediate compounds thereto.

  2-氨基-和 2-（取代氨基）-四氢-和-顺式-六氢-咔唑，可用于减轻哺乳动物的抑郁症及其中间化合物。