1-(2',4'-dimethoxyphenyl)-3,4-dihydro-β-carboline

• 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)-3,4-dihydro-β-carboline
• 英文别名: 1-(2,4-dimethoxyphenyl)-3,4-dihydro-β-carboline；1-(2,4-dimethoxyphenyl)-4,9-dihydro-3H-pyrido[3,4-b]indole
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: VOICDFFTSZWUFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  46.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2',4'-dimethoxyphenyl)-1,2,3,4-tetrahydro-β-carboline 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 1-(2',4'-dimethoxyphenyl)-3,4-dihydro-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

• The Preparation and Evaluation of 1-Substituted 1,2,3,4-Tetrahydro- and 3,4-Dihydro-.BETA.-carboline Derivatives as Potential Antitumor Agents
  作者：Ya-Ching Shen、Ching-Yeu Chen、Pei-Wen Hsieh、Chang-Yih Duh、Yat-Min Lin、Chin-Lien Ko

  DOI：10.1248/cpb.53.32

  日期：——

  A series of 1-substituted 1,2,3,4-tetrahydro- and 3,4-dihydro-β-carboline derivatives have been synthesized and evaluated for antitumor activity against murine P-388 and human tumor cell lines, KB-16, A-549 and HT-29. All of the compounds prepared, except for 19, showed significant cytotoxicity. Among them, compound 29 exhibited the most potent activity against all tested tumor cell lines. There was an apparent lack of correlation regarding cytotoxicity between 1,2,3,4-tetrahydro- and 3,4-dihydro-β-carbolines. This study is the first to discover compound 29 as a potential lead for the development of future anticancer agents. The mode of inhibition for compound 29 was proposed.

  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。
• 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。
• Synthetic study on the T3P®-promoted one-pot preparation of 1-substituted-3,4-dihydro-β-carbolines by the reaction of tryptamine with carboxylic acids
  作者：Péter Ábrányi-Balogh、Tamás Földesi、Alajos Grün、Balázs Volk、György Keglevich、Mátyás Milen

  DOI：10.1016/j.tetlet.2016.03.067

  日期：2016.5

  novel and efficient one-pot method has been developed for the synthesis of 1-substituted-3,4-dihydro-β-carbolines from tryptamine and a wide variety of carboxylic acids. The reaction was successfully applied to the synthesis of an important alkaloid harmalan as well as dihydro-eudistomin-U. This represents the first case in which 1-propanephosphonic acid cyclic anhydride (T3P®) has been used in the

  已经开发了一种新颖且有效的一锅法，该方法可从色胺和多种羧酸中合成1-取代的3,4-二氢-β-咔啉。该反应已成功地用于重要的生物碱harmalan以及二氢大黄素-U的合成。这代表在Bischler-Napieralski反应中使用1-丙烷膦酸环酐（T3P®）的第一种情况。出乎意料的是，观察到少于两个当量的试剂足以完成两个连续的反应。
• US6720331B2
  申请人：——

  公开号：US6720331B2

  公开（公告）日：2004-04-13
• Iodine-catalyzed chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines: A short synthesis of Kumujian-C, Eudistomin-U, Norharmane, Harmane Harmalan and Isoeudistomine-M
  作者：Sunil Gaikwad、Dayanand Kamble、Pradeep Lokhande

  DOI：10.1016/j.tetlet.2018.04.043

  日期：2018.6

  Temperature controlled chemoselective dehydrogenation and aromatization of tetrahydro-β-carbolines, using molecular I2 and H2O2, in DMSO solvent affords a practical access to a series of corresponding 3,4-dihydro-β-carbolines and β-carbolines respectively. This method has been successfully employed in the short synthesis of Kumujian-C, Eudistomin-U, Norharmane Harmane Harmalan and Isoeudistomin-M.

  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。