1-(2',4'-dimethoxyphenyl)-1,2,3,4-tetrahydro-β-carboline | 404925-67-3

• 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',4'-dimethoxyphenyl)-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 1-(2',4'-Dimethoxyphenyl)-1,2,3,4-tetrahydro-beta-carboline；1-(2,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 404925-67-3
• 化学式: C₁₉H₂₀N₂O₂
• 分子量: 308.38
• InChiKey: SSLNFDGKAGXRFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2',4'-dimethoxyphenyl)-1,2,3,4-tetrahydro-β-carboline 在 双氧水 、 碘 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 12.0h， 以89%的产率得到1-(2,4-dimethoxyphenyl)-9H-pyrido[3,4-b]indole
  参考文献：
  名称：

  碘催化四氢-β-咔啉的化学选择性脱氢和芳构化：Kumujian-C，Eudistomin-U，Norharmane，Harmane Harmalan和Isoeudistomine-M的短合成

  摘要：

  在DMSO溶剂中使用分子I 2和H 2 O 2对四氢-β-咔啉进行温度控制的化学选择性脱氢和芳构化，可分别实际获得一系列相应的3,4-二氢-β-咔啉和β-咔啉。该方法已成功用于Kumujian-C，Eudistomin-U，Norharmane Harmane Harmalan和Isoeudistomin-M的短合成中。

  DOI：

  10.1016/j.tetlet.2018.04.043
• 作为产物：
  描述：

  色胺 、 2,4-二甲氧基苯甲醛 在 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 1-(2',4'-dimethoxyphenyl)-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  The Preparation and Evaluation of 1-Substituted 1,2,3,4-Tetrahydro- and 3,4-Dihydro-.BETA.-carboline Derivatives as Potential Antitumor Agents

  摘要：

  合成了一系列1-取代的1,2,3,4-四氢-和3,4-二氢-β-卡boline衍生物，并评估了它们对小鼠P-388和人类肿瘤细胞系KB-16、A-549和HT-29的抗肿瘤活性。除化合物19外，所有合成的化合物均表现出显著的细胞毒性。其中，化合物29对所有测试的肿瘤细胞系表现出最强的活性。在1,2,3,4-四氢-β-卡boline和3,4-二氢-β-卡boline之间的细胞毒性并没有明显的相关性。本研究首次发现化合物29作为开发未来抗癌药物的潜在先导。为化合物29提出了抑制机制的假设。

  DOI：

  10.1248/cpb.53.32

文献信息

• 1-substituted 1,2,3,4-tetrahydro-beta-carboline and 3,4-dihydro-beta-carboline and analogs as antitumor agents
  申请人：——

  公开号：US20030040527A1

  公开（公告）日：2003-02-27

  A composition includes a substituted dihydro- or tetrahydro-&bgr;-carboline of formula (II) or (III), wherein the aromatic ring of the carboline may include one or more substituents selected from the group consisting of hydroxy, C 1-6 alkoxy, benzyloxy, C 1-6 acyloxy, amino, C 1-6 alkyl, C 1-6 dialkylamino, halogen, and carboxy, and the C-1 position of the carboline may include a substitutent selected from the group consisting of a carbocyclic group and a heterocyclic group. The composition may include a salt or a prodrug of the substituted dihydro- or tetrahydro-&bgr;-carboline. The composition may further includes a pharmaceutically acceptable carrier, diluent, or excipient.

  该组成物包括公式（II）或（III）的取代二氢或四氢-β-咔啉，其中咔啉的芳香环可以包括羟基，C1-6烷氧基，苄氧基，C1-6酰氧基，氨基，C1-6烷基，C1-6二烷基氨基，卤素和羧基等基团中的一个或多个取代基，而咔啉的C-1位置可以包括来自羰环和杂环基团中的一个取代基。该组成物可以包括取代二氢或四氢-β-咔啉的盐或前药。该组成物还可以包括药学上可接受的载体，稀释剂或赋形剂。
• 1-substituted 1,2,3,4-tetrahydro-&bgr;-carboline and 3,4-dihydro-&bgr;-carboline and analogs as antitumor agents
  申请人：National Sun Yat-sen University

  公开号：US06720331B2

  公开（公告）日：2004-04-13

  A composition includes a substituted dihydro- or tetrahydro-&bgr;-carboline of formula (II) or (III), wherein the aromatic ring of the carboline may include one or more substituents selected from the group consisting of hydroxy, C1-6 alkoxy, benzyloxy, C1-6 acyloxy, amino, C1-6 alkyl, C1-6 dialkylamino, halogen, and carboxy, and the C-1 position of the carboline may include a substitutent selected from the group consisting of a carbocyclic group and a heterocyclic group. The composition may include a salt or a prodrug of the substituted dihydro- or tetrahydro-&bgr;-carboline. The composition may further includes a pharmaceutically acceptable carrier, diluent, or excipient.

  该组合物包括式（II）或（III）的取代二氢或四氢-β-咔啉，其中咔啉的芳香环可能包括一种或多种取代基，所述取代基选自羟基，C1-6烷氧基，苄氧基，C1-6酰氧基，氨基，C1-6烷基，C1-6二烷基氨基，卤素和羧基的群，而咔啉的C-1位置可能包括一个选自环烷基和杂环基的取代基。该组合物可能包括取代的二氢或四氢-β-咔啉的盐或前药。该组合物可能进一步包括药用可接受的载体，稀释剂或赋形剂。
• METHODS FOR TREATING CANCER AND NON-NEOPLASTIC CONDITIONS
  申请人：Almstead Neil

  公开号：US20120202763A1

  公开（公告）日：2012-08-09

  Compounds that selectively inhibit pathological production of human vascular endothelial growth factor (VEGF) and compositions comprising such Compounds are described. Compounds that inhibit viral replication or the production of viral RNA or DNA or viral protein and compositions comprising such Compounds are described. Also described are methods of reducing VEGF using such Compounds and methods for treating cancer and non-neoplastic conditions involving the administration of such Compounds. Further described are methods of inhibiting viral replication or the production of viral RNA or DNA or viral protein using such Compounds and methods for treating viral infections involving the administration of such Compounds. The Compounds may be administered as a single agent therapy or in combination with one or more additional therapies to a human in need of such treatments.

  本文介绍了选择性抑制人类血管内皮生长因子（VEGF）病理性产生的化合物以及包含这些化合物的组合物。本文还介绍了抑制病毒复制或病毒RNA或DNA或病毒蛋白质产生的化合物以及包含这些化合物的组合物。同时，本文还介绍了使用这些化合物减少VEGF的方法以及使用这些化合物治疗癌症和非肿瘤性疾病的方法。本文还介绍了使用这些化合物抑制病毒复制或病毒RNA或DNA或病毒蛋白质产生的方法以及使用这些化合物治疗病毒感染的方法。这些化合物可以作为单一治疗剂或与一个或多个其他治疗剂联合使用，用于治疗需要这些治疗的人类。
• METHODS FOR TREATING NEUROFIBROMATOSIS
  申请人：Cao Liangxian

  公开号：US20120157401A1

  公开（公告）日：2012-06-21

  Methods for treating neurofibromatosis involving the administration of a compound that selectively inhibits pathological production of human VEGF are described. The compound can be administered as a single-agent therapy or in combination with one or more additional therapies to a human in need of such treatment.
• METHODS FOR TREATING KAPOSI SARCOMA
  申请人：Cao Liangxian

  公开号：US20120157400A1

  公开（公告）日：2012-06-21

  Methods for treating Kaposi's sarcoma involving the administration of a compound that selectively inhibits pathological production of human VEGF are described. The compound can be administered as a single-agent therapy or in combination with one or more additional therapies to a human in need of such treatment.