3-hydroxy-6-methoxy-1,2,3,4-tetrahydrocarbazole | 20802-22-6

• 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: 3-hydroxy-6-methoxy-1,2,3,4-tetrahydrocarbazole
• 英文别名: 6-methoxy-1,2,3,4-tetrahydro-carbazol-3-ol；3-hydroxy-6-methoxy1,2,3,4-tetrahydrocarbazole；6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-ol；3-Hydroxy-6-methoxy-1,2,3,4-tetrahydro-carbazol；1,2,3,4-Tetrahydro-3-hydroxy-6-methoxycarbazol；3-(Hydroxy)-6-methoxy-1,2,3,4-tetrahydrocarbazole
• CAS: 20802-22-6
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: PJBKSQRIAFHVIW-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C
• 沸点：
  421.9±45.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-6-methoxy-1,2,3,4-tetrahydrocarbazole 在 sodium azide 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 反应 34.0h， 生成 3-azido-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole
  参考文献：
  名称：

  Bird, C. W.; Wee, A. G. H., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 191 - 192

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(苄氧基)环已酮 在 溶剂黄146 作用下， 以 氢氧化钾 、 乙醇 为溶剂， 反应 10.17h， 生成 3-hydroxy-6-methoxy-1,2,3,4-tetrahydrocarbazole
  参考文献：
  名称：

  Bird, C. W.; Wee, A. G. H., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 191 - 192

  摘要：

  DOI：

文献信息

• 3-Amido-1,2,3,4-tetrahydrocarbazoles
  申请人：Sterling Drug Inc.

  公开号：US03959309A1

  公开（公告）日：1976-05-25

  3-(Substituted-amino)-1,2,3,4-tetrahydrocarbazoles are prepared by reacting appropriate 4-substituted-aminocyclohexanones with a phenylhydrazine, by reacting a 3-(sulfonyloxy)-1,2,3,4-tetrahydrocarbazole with an appropriate substituted amine, or by reduction of an appropriate 3-(acylamino)-1,2,3,4-tetrahydrocarbazole. The 3-(substituted-amino)-1,2,3,4-tetrahydrocarbazoles of this invention have analgetic and psychotropic activities. Moreover, certain of these compounds also have antihistaminic activity.

  通过将适当的4-取代氨基环己酮与苯基肼反应，通过将3-(磺酰氧基)-1,2,3,4-四氢咔唑与适当的取代胺反应，或者通过还原适当的3-(酰胺基)-1,2,3,4-四氢咔唑，可以制备3-(取代氨基)-1,2,3,4-四氢咔唑。本发明的这些3-(取代氨基)-1,2,3,4-四氢咔唑具有镇痛和精神活性。此外，这些化合物中的某些化合物还具有抗组胺活性。
• 3-Hydroxy carbazole derivatives
  申请人：Sterling Drug Inc.

  公开号：US04062864A1

  公开（公告）日：1977-12-13

  3-(Substituted-amino)-1,2,3,4-tetrahydrocarbazoles are prepared by reacting appropriate 4-substituted-aminocyclohexanones with a phenylhydrazine, by reacting a 3-(sulfonyloxy)-1,2,3,4-tetrahydrocarbazole with an appropriate substituted amine, or by reduction of an appropriate 3-(acylamino)-1,2,3,4-tetrahydrocarbazole. The 3-(substituted-amino)-1,2,3,4-tetrahydrocarbazoles of this invention have analgetic and psychotropic activities. Moreover, certain of these compounds also have antihistaminic activity.

  3-(取代氨基)-1,2,3,4-四氢咔唑烯通过将适当的4-取代氨基环己酮与苯基肼反应制备，通过将3-(磺酸酯氧基)-1,2,3,4-四氢咔唑烯与适当的取代胺反应制备，或者通过还原适当的3-(酰胺基)-1,2,3,4-四氢咔唑烯来制备。本发明的3-(取代氨基)-1,2,3,4-四氢咔唑烯具有镇痛和精神活性。此外，其中一些化合物还具有抗组胺活性。
• 3-Amino-tetrahydrocarbazoles
  申请人：Sterling Drug Inc.

  公开号：US04172834A1

  公开（公告）日：1979-10-30

  3-(Substituted-amino)-1,2,3,4-tetrahydrocarbazoles are prepared by reacting appropriate 4-substituted-aminocyclohexanones with a phenylhydrazine, by reacting a 3-(sulfonyloxy)-1,2,3,4-tetrahydrocarbazole with an appropriate substituted amine, or by reduction of an appropriate 3-(acylamino)-1,2,3,4-tetrahydrocarbazole. The 3-(substituted-amino)-1,2,3,4-tetrahydrocarbazoles of this invention have analgetic and psychotropic activities. Moreover, certain of these compounds also have antihistaminic activity.

  本发明涉及通过将适当的4-取代氨基环己酮与苯肼反应，通过将3-(磺酰氧基)-1,2,3,4-四氢咔唑与适当的取代胺反应，或通过还原适当的3-(酰胺基)-1,2,3,4-四氢咔唑来制备3-(取代氨基)-1,2,3,4-四氢咔唑。本发明的3-(取代氨基)-1,2,3,4-四氢咔唑具有镇痛和精神活性。此外，其中某些化合物还具有抗组胺活性。
• TRICYCLIC CYTOPROTECTIVE COMPOUNDS
  申请人：Wulfert Ernst

  公开号：US20090259043A1

  公开（公告）日：2009-10-15

  Compounds of formula (I): [in which: X is a group of formula >CR 1 R 2 or >SO 2 ; Y is a group of formula >NH or >CR 1 R 2 ; Z is a group of formula >C═O or >CH 2 or a direct bond; R 1 is hydrogen and R 2 is hydrogen, carboxy or hydroxy; or R 1 and R 2 together represent an oxo group, a methylenedioxy group or a hydroxyimino group; R 3 is hydrogen or lower alkyl; R 4 represents two hydrogen atoms, or an oxo or hydroxyimino group; R 5 is hydrogen, lower alkyl or halogen; R 6 is hydrogen, lower alkoxy or carboxy; R 7 and R 8 are each hydrogen, lower alkyl or halogen; and pharmaceutically acceptable salts and esters thereof can be used for the treatment or prophylaxis of acute or chronic neurodegenerative diseases or conditions such as Alzheimer's Disease, Parkinson's Disease, Huntington's Chorea, Multiple Sclerosis or the sequelae to acute ischaemic events such as heart attack, stroke or head injury and for protection against ischaemic damage to tissues of peripheral organs.

  式(I)的化合物：[其中：X是公式>CR1R2或>SO2的基团；Y是公式>NH或>CR1R2的基团；Z是公式>C═O或>CH2或直接键的基团；R1是氢原子，R2是氢原子，羧基或羟基；或R1和R2一起代表氧代基、甲亚基二氧基基团或羟基亚胺基团；R3是氢原子或较低的烷基；R4代表两个氢原子或氧代基或羟基亚胺基团；R5是氢原子、较低的烷基或卤素；R6是氢原子、较低的烷氧基或羧基；R7和R8均为氢原子、较低的烷基或卤素；以及其药学上可接受的盐和酯，可用于治疗或预防急性或慢性神经退行性疾病或病症，如阿尔茨海默病、帕金森病、亨廷顿舞蹈病、多发性硬化症或急性缺血事件的后遗症，如心脏病发作、中风或头部损伤，并用于保护外周器官组织免受缺血性损伤。
• Tricyclic Cytoprotective Compounds
  申请人：Wulfert Ernst

  公开号：US20080146644A1

  公开（公告）日：2008-06-19

  Compounds of formula (I): [in which: X is a group of formula >CR 1 R 2 or >SO 2 ; Y is a group of formula >NH or >CR 1 R 2 ; Z is a group of formula >C═O or >CH 2 or a direct bond; R 1 is hydrogen and R 2 is hydrogen, carboxy or hydroxy; or R 1 and R 2 together represent an oxo group, a methylenedioxy group or a hydroxyimino group; R 3 is hydrogen or lower alkyl; R 4 represents two hydrogen atoms, or an oxo or hydroxyimino group; R 5 is hydrogen, lower alkyl or halogen; R 6 is hydrogen, lower alkoxy or carboxy; R 7 and R 8 are each hydrogen, lower alkyl or halogen; and pharmaceutically acceptable salts and esters thereof can be used for the treatment or prophylaxis of acute or chronic neurodegenerative diseases or conditions such as Alzheimer's Disease, Parkinson's Disease, Huntington's Chorea, Multiple Sclerosis or the sequelae to acute ischaemic events such as heart attack, stroke or head injury and for protection against ischaemic damage to tissues of peripheral organs.

  化合物的公式 (I)：[其中：X 是公式 >CR1R2 或 >SO2 的基团；Y 是公式 >NH 或 >CR1R2 的基团；Z 是公式 >C═O 或 >CH2 或直接键；R1 是氢原子，R2 是氢原子，羧基或羟基；或者 R1 和 R2 一起表示一个氧代基团、一个甲二氧基基团或一个羟肟基团；R3 是氢原子或低碳基；R4 表示两个氢原子，或一个氧代基团或羟肟基团；R5 是氢原子、低碳基或卤素；R6 是氢原子、低烷氧基或羧基；R7 和 R8 分别是氢原子、低碳基或卤素；以及其药学上可接受的盐和酯，可用于治疗或预防急性或慢性神经退行性疾病或病症，如阿尔茨海默病、帕金森病、亨廷顿舞蹈病、多发性硬化症或急性缺血事件的后遗症，如心脏病发作、中风或头部损伤，并保护外围器官组织免受缺血损伤。