2,7-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole | 33657-41-9

• 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: 2,7-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
• 英文别名: 2,7-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；2,7-dimethyl-1,3,4,5-tetrahydropyrido[4,3-b]indole
• CAS: 33657-41-9
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: KMOQRWCHESCPKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-溴丙氧基)-4-氯苯 、 2,7-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 以61.5%的产率得到5-(3-(4-chlorophenoxy)propyl)-2,7-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Novel Carboline Derivatives as Potent Antifungal Lead Compounds: Design, Synthesis, and Biological Evaluation

  摘要：

  A series of novel antifungal carboline derivatives was designed and synthesized, which showed broad-spectrum antifungal activity. Particularly, compound C38 showed comparable in vitro antifungal activity to fluconazole without toxicity to human embryonic lung cells. It also exhibited good fungicidal activity against both fluconazole-sensitive and -resistant Candida albicans cells and had potent inhibition activity against Candida albicans biofilm formation and hyphal growth. Moreover, C38 showed good synergistic antifungal activity in combination with fluconazole (FLC) against FLC-resistant Candida species. Preliminary mechanism studies revealed that C38 might act by inhibiting the synthesis of fungal cell wall.

  DOI：

  10.1021/ml400492t
• 作为产物：
  描述：

  3-(2-Azido-4-methylphenyl)pyridine 在 sodium tetrahydroborate 、 水合三氯化钌 作用下， 以 甲醇 、 二氯甲烷 、 醋酸异丙酯 、 水 为溶剂， 反应 15.0h， 生成 2,7-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  钌催化芳基叠氮化物形成 γ-碳鎓离子；二甲酚的合成

  摘要：

  通过 3-吡啶基取代的芳基叠氮化物的钌 (III) 催化反应，立体选择性地生产一系列 γ-咔啉。其他催化剂和条件既没有那么选择性，也没有那么高产率。该方法用于简洁、高效地合成二甲苯啉。

  DOI：

  10.1021/ol2008268

文献信息

• Second-Generation Histone Deacetylase 6 Inhibitors Enhance the Immunosuppressive Effects of Foxp3+ T-Regulatory Cells
  作者：Jay H. Kalin、Kyle V. Butler、Tatiana Akimova、Wayne W. Hancock、Alan P. Kozikowski

  DOI：10.1021/jm200773h

  日期：2012.1.26

  Second-generation Tubastatin A analogues were synthesized and evaluated for their ability to inhibit selectively histone deacetylase 6 (HDAC6). Substitutions to the carboline cap group were well-tolerated with substitution at the 2-position of both beta- and gamma-carbolines being optimal for HDAC6 activity and selectivity. Some compounds in this series were determined to have subnanomolar activity at HDAC6 with more than 7000 fold selectivity for HDAC6 versus HDAC1. Selected compounds were then evaluated for their ability to augment the immunosuppressive effect of Foxp3+ regulatory T cells. All compounds tested were found to enhance the ability of regulatory T cells to inhibit the mitotic division of effector T cells both in vitro and in vivo, suggesting that further investigation into the use of these compounds for the treatment of autoimmune disorders is warranted.
• (1-Azinone)-Substituted Pyridoindoles
  申请人：Albany Molecular Research, Inc.

  公开号：EP2476680B1

  公开（公告）日：2014-08-27
• [EN] HETEROCYCLIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS UTILISATIONS
  申请人：GIRAFPHARMA LLC

  公开号：WO2019074979A1

  公开（公告）日：2019-04-18

  Heterocyclic compounds as Weel inhibitors are provided. The compounds may find therapeutic agents for the treatment of diseases and may find particular use in oncology.
• Novel Carboline Derivatives as Potent Antifungal Lead Compounds: Design, Synthesis, and Biological Evaluation
  作者：Shengzheng Wang、Yan Wang、Wei Liu、Na Liu、Yongqiang Zhang、Guoqiang Dong、Yang Liu、Zhengang Li、Xiaomeng He、Zhenyuan Miao、Jianzhong Yao、Jian Li、Wannian Zhang、Chunquan Sheng

  DOI：10.1021/ml400492t

  日期：2014.5.8

  A series of novel antifungal carboline derivatives was designed and synthesized, which showed broad-spectrum antifungal activity. Particularly, compound C38 showed comparable in vitro antifungal activity to fluconazole without toxicity to human embryonic lung cells. It also exhibited good fungicidal activity against both fluconazole-sensitive and -resistant Candida albicans cells and had potent inhibition activity against Candida albicans biofilm formation and hyphal growth. Moreover, C38 showed good synergistic antifungal activity in combination with fluconazole (FLC) against FLC-resistant Candida species. Preliminary mechanism studies revealed that C38 might act by inhibiting the synthesis of fungal cell wall.
• Ruthenium-Catalyzed γ-Carbolinium Ion Formation from Aryl Azides; Synthesis of Dimebolin
  作者：Huijun Dong、Regina T. Latka、Tom G. Driver

  DOI：10.1021/ol2008268

  日期：2011.5.20

  A range of γ-carbolines were produced stereoselectively from ruthenium(III)-catalyzed reactions of 3-pyridyl substituted aryl azides. Other catalysts and conditions were neither as selective nor as high-yielding. This method was used to synthesize dimebolin in a concise and efficient manner.

  通过 3-吡啶基取代的芳基叠氮化物的钌 (III) 催化反应，立体选择性地生产一系列 γ-咔啉。其他催化剂和条件既没有那么选择性，也没有那么高产率。该方法用于简洁、高效地合成二甲苯啉。