2-(2-butynyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole

• 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-(2-butynyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole
• 英文别名: 2-but-2-ynyl-10-methyl-3,4-dihydro-1H-pyrazino[1,2-a]indole
• 化学式: C₁₆H₁₈N₂
• 分子量: 238.332
• InChiKey: PVQUODDLIAELAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 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：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1H-吲哚-1-乙胺,3-甲基- 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 10.0h， 生成 2-(2-butynyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole
  参考文献：
  名称：

  Novel Synthesis of 1,2,3,4-Tetrahydropyrazino[1,2-a]indoles

  摘要：

  Condensation of 2-(3-methyl-1H-indol-1-yl)ethylamine (7) with benzotriazole and formaldehyde gave 2-(1-H-1,2,3-benzotriazol-1-ylmethyl)-10-methyl-1,2,3,4-tetrahydro-pyrazino[1,2-alpha]indole (8) in 96% yield. Nucleophilic substitutions of the benzotriazolyl group in 8 with NaBH4, NaCN, triethyl phosphite, allylsilanes, silyl enol ether and Grignard reagents afforded novel 10-methyl-1,2,3,4-tetrahydropyrazino[1,2-alpha]indoles 9a-i in 78-95% yields.

  DOI：

  10.1021/jo026922x

文献信息

• Novel Synthesis of 1,2,3,4-Tetrahydropyrazino[1,2-<i>a</i>]indoles
  作者：Alan R. Katritzky、Akhilesh Kumar Verma、Hai-Ying He、Ramesh Chandra

  DOI：10.1021/jo026922x

  日期：2003.6.1

  Condensation of 2-(3-methyl-1H-indol-1-yl)ethylamine (7) with benzotriazole and formaldehyde gave 2-(1-H-1,2,3-benzotriazol-1-ylmethyl)-10-methyl-1,2,3,4-tetrahydro-pyrazino[1,2-alpha]indole (8) in 96% yield. Nucleophilic substitutions of the benzotriazolyl group in 8 with NaBH4, NaCN, triethyl phosphite, allylsilanes, silyl enol ether and Grignard reagents afforded novel 10-methyl-1,2,3,4-tetrahydropyrazino[1,2-alpha]indoles 9a-i in 78-95% yields.
• Synthesis and antifungal activity of substituted-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indoles
  作者：Rakesh Kumar Tiwari、Akhilesh K. Verma、Anil K. Chhillar、Devender Singh、Jaspal Singh、V. Kasi Sankar、Vibha Yadav、G.L. Sharma、Ramesh Chandra

  DOI：10.1016/j.bmc.2005.11.054

  日期：2006.4

  Series of substituted-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indoles derivatives have been synthesized and examined for their activity against pathogenic strains of Aspergillus fumigatus (ITCC 4517), Aspergillus flavus (ITCC 5192) Aspergillus niger (ITCC 5405) and Candida albicans (ITCC No 4718). All synthesized compounds showed mild to moderate activity, except for 2-substituted-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indoles 6a-d. The most active 1-(4-chlorophenyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole 4c exhibited a MIC value of 5.85 mu g/disc against A. fumigatus and 11.71 mu g/disc against A. flavus and A. niger in disc diffusion assay. Anti-Aspergillus activity of active compound 4c by microbroth dilution assay was found to be 15.62 mu g/ml in case of A. fumigatus and 31.25 mu g/ml with A. flavus and A. niger. The MIC90 value of the most active compound by percent germination inhibition assay was found to be 15.62 mu g/ml against A. fumigatus. The MIC90 values of substituted-10-methyl-1,2,3, 4-tetrahydropyrazino[1,2-a]indoles against C albicans ranged from 15.62 to 250 mu g/ml. The in vitro toxicity of the most active I(4-chlorophenyl)-10-methyl-1,2,3,4-tetrahydropyi-azino[1,2-a]indole 4c was evaluated using haemolytic assay, in which the compound was found to be non-toxic to human erythrocytes Lip to a concentration of 312.50 mu g/ml. The standard drug amphotericin B exhibited 100% lysis at a concentration of 37.5 mu g/ml. (c) 2006 Elsevier Ltd. All rights reserved.