1,2,3,4-tetrahydro-6-hydroxy-1-phenyl-β-carboline | 18647-13-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1,2,3,4-tetrahydro-6-hydroxy-1-phenyl-β-carboline
• 英文别名: 1-phenyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-6-ol；1-Phenyl-6-hydroxy-1,2,3,4-tetrahydro-2-carbolin；1-Phenyl-6-hydroxy-1,2,3,4-tetrahydro-2-carboline；1-phenyl-2,3,4,9-tetrahydro-1H-β-carbolin-6-ol；1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-6-ol
• CAS: 18647-13-7
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: CXHLMCAMGSKZMU-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  502.5±45.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-6-hydroxy-1-phenyl-β-carboline 在 palladium 10% on activated carbon 作用下， 以53%的产率得到1-phenyl-9H-pyrido[3,4-b]indol-6-ol
  参考文献：
  名称：

  [EN] BETA-CARBOLINES AS POSITIVE ALLOSTERIC MODULATORS OF THE HUMAN SEROTONIN RECEPTOR 2C (5-HT2C)
  [FR] BÊTA-CARBOLINES SERVANT DE MODULATEURS ALLOSTÉRIQUES POSITIFS DU RÉCEPTEUR HUMAIN DE LA SÉROTONINE 2C (5-HT2C)

  摘要：

  本发明涉及新型小分子，其合成方法和用于调节人类血清素受体2C（5-HT2c）活性的用途，优选地具有选择性。这些小分子具有取代的β-咔啉核心结构，可以在一个或多个键处选择性地饱和，以提供二氢β-咔啉核心或四氢β-咔啉核心。这些小分子可用于治疗和/或预防与人类血清素受体2C（5-HT2C）相关的疾病、障碍和/或病况，包括认知障碍、成瘾和强迫症等精神、心理和/或神经疾病、障碍和病况。还可以通过抑制食欲治疗和/或预防肥胖症。

  公开号：

  WO2020072675A1
• 作为产物：
  描述：

  5-羟基色胺盐酸盐 、 苯甲醛 以 N,N-二甲基甲酰胺 为溶剂， 以32%的产率得到1,2,3,4-tetrahydro-6-hydroxy-1-phenyl-β-carboline
  参考文献：
  名称：

  [EN] BETA-CARBOLINES AS POSITIVE ALLOSTERIC MODULATORS OF THE HUMAN SEROTONIN RECEPTOR 2C (5-HT2C)
  [FR] BÊTA-CARBOLINES SERVANT DE MODULATEURS ALLOSTÉRIQUES POSITIFS DU RÉCEPTEUR HUMAIN DE LA SÉROTONINE 2C (5-HT2C)

  摘要：

  本发明涉及新型小分子，其合成方法和用于调节人类血清素受体2C（5-HT2c）活性的用途，优选地具有选择性。这些小分子具有取代的β-咔啉核心结构，可以在一个或多个键处选择性地饱和，以提供二氢β-咔啉核心或四氢β-咔啉核心。这些小分子可用于治疗和/或预防与人类血清素受体2C（5-HT2C）相关的疾病、障碍和/或病况，包括认知障碍、成瘾和强迫症等精神、心理和/或神经疾病、障碍和病况。还可以通过抑制食欲治疗和/或预防肥胖症。

  公开号：

  WO2020072675A1

文献信息

• The Chemistry of Indoles. CVII. A Novel Synthesis of 3,4,5,6-Tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indoles and a New Finding on Pictet-Spengler Reaction.
  作者：Masanori SOMEI、Sakiko TERANISHI、Koji YAMADA、Fumio YAMADA

  DOI：10.1248/cpb.49.1159

  日期：——

  4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indoles by simple heating with amines under an oxygen atmosphere. Serotonins also reacted with various aldehydes to provide 3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indoles rather than beta-carbolines under basic conditions. In these novel reactions, the presence of the 5-hydroxy group on the indole nucleus was suggested to be essential. Possible

  发现5-羟色胺通过在氧气气氛下简单地与胺加热而产生3,4,5,6-四氢-7-羟基-1H-氮杂环庚烷[5,4,3-cd]吲哚。在碱性条件下，5-羟色胺还与各种醛反应生成3,4,5,6-四氢-7-羟基-1H-氮杂环庚烷[5,4,3-cd]吲哚而不是β-咔啉。在这些新颖的反应中，吲哚核上5-羟基的存在被认为是必不可少的。讨论了可能的机制。
• ADMINISTRATION OF CARBOLINE DERIVATIVES USEFUL IN THE TREATMENT OF CANCER AND OTHER DISEASES
  申请人：Cao Liangxian

  公开号：US20070254878A1

  公开（公告）日：2007-11-01

  In accordance with the present invention, compounds that inhibit the expression of VEGF post-transcriptionally have been identified, and compositions, and methods for the administration and use of those compounds. provided. In one aspect of the invention, compounds useful in the inhibition of VEGF production, in the treatment of solid tumor cancer, and in reducing serum, plasma, and/or tumor VEGF levels, are provided. In another aspect of the invention, methods are provided for the inhibition of VEGF production, the treatment of cancer, and the reduction of plasma and/or tumor VEGF levels, using the compounds of the invention.

  根据本发明，已经鉴定出了抑制VEGF在转录后表达的化合物，以及这些化合物的组合物、管理和使用方法。在发明的一个方面，提供了在抑制VEGF生产、治疗实体肿瘤癌和减少血清、血浆和/或肿瘤VEGF水平方面有用的化合物。在发明的另一个方面，提供了使用本发明的化合物抑制VEGF生产、治疗癌症和减少血浆和/或肿瘤VEGF水平的方法。
• Carboline Derivatives Useful in the Inhibition of Angiogenesis
  申请人：MOON Young-Choon

  公开号：US20070281962A2

  公开（公告）日：2007-12-06

  In accordance with the present invention, compounds that inhibit the expression of VEGF post-transcriptionally have been identified, and methods for their use provided. In one aspect of the invention, compounds useful in the inhibition of VEGF production, in the inhibition of angiogenesis, and/or in the treatment of cancer, diabetic retinopathy or exudative macular degeneration are provided. In another aspect of the invention, methods are provided for the inhibition of VEGF production, the inhibition of angiogenesis, and/or the treatment of cancer, diabetic retinopathy or exudative macular degeneration using the compounds of the invention.

  根据本发明，已经鉴定出了抑制VEGF转录后表达的化合物，并提供了它们的使用方法。在本发明的一个方面，提供了在抑制VEGF产生、抑制血管生成和/或治疗癌症、糖尿病视网膜病变或渗出性黄斑变性方面有用的化合物。在本发明的另一个方面，提供了使用本发明中的化合物抑制VEGF产生、抑制血管生成和/或治疗癌症、糖尿病视网膜病变或渗出性黄斑变性的方法。
• CARBOLINE DERIVATIVES USEFUL IN THE INHIBITION OF ANGIOGENESIS
  申请人：MOON Young-Choon

  公开号：US20110160190A1

  公开（公告）日：2011-06-30

  In accordance with the present invention, compounds that inhibit the expression of VEGF post-transcriptionally have been identified, and methods for their use provided. In one aspect of the invention, compounds useful in the inhibition of VEGF production, in the treatment of solid tumor cancer, and in reducing plasma and/or tumor VEGF levels, are provided. In another aspect of the invention, methods are provided for the inhibition of VEGF production, the treatment of cancer, and the reduction of plasma and/or tumor VEGF levels, using the compounds of the invention.

  根据本发明，已经确定了抑制VEGF在转录后表达的化合物，并提供了其使用方法。在本发明的一个方面中，提供了用于抑制VEGF产生、治疗实体肿瘤癌和降低血浆和/或肿瘤VEGF水平的化合物。在本发明的另一个方面中，提供了使用本发明的化合物抑制VEGF产生、治疗癌症和降低血浆和/或肿瘤VEGF水平的方法。
• CARBOLINE DERIVATIVES USEFUL IN THE TREATMENT OF CANCER AND OTHER DISEASES
  申请人：Cao Liangxian

  公开号：US20120129841A1

  公开（公告）日：2012-05-24

  In accordance with the present invention, compounds that inhibit the expression of VEGF post-transcriptionally have been identified, and compositions, and methods for the administration and use of those compounds. provided. In one aspect of the invention, compounds useful in the inhibition of VEGF production, in the treatment of solid tumor cancer, and in reducing serum, plasma, and/or tumor VEGF levels, are provided. In another aspect of the invention, methods are provided for the inhibition of VEGF production, the treatment of cancer, and the reduction of plasma and/or tumor VEGF levels, using the compounds of the invention.

  根据本发明，已经鉴定出抑制VEGF转录后表达的化合物，以及这些化合物的组合物、用于管理和使用这些化合物的方法。在本发明的一个方面，提供了在抑制VEGF产生、治疗实体肿瘤癌和减少血清、血浆和/或肿瘤VEGF水平方面有用的化合物。在本发明的另一个方面，提供了使用本发明的化合物抑制VEGF产生、治疗癌症和减少血浆和/或肿瘤VEGF水平的方法。