2-(1H-1,2,3-benzotriazol-1-ylmethyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole | 561305-29-1

• 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-(1H-1,2,3-benzotriazol-1-ylmethyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole
• 英文别名: 2-(benzotriazol-1-ylmethyl)-10-methyl-3,4-dihydro-1H-pyrazino[1,2-a]indole
• CAS: 561305-29-1
• 化学式: C₁₉H₁₉N₅
• 分子量: 317.393
• InChiKey: NWFYYKISLISXSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1H-1,2,3-benzotriazol-1-ylmethyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到2,10-dimethyl-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
• 作为产物：
  描述：

  3-甲基吲哚 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 乙腈 为溶剂， 反应 36.0h， 生成 2-(1H-1,2,3-benzotriazol-1-ylmethyl)-10-methyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole
  参考文献：
  名称：

  Synthesis and antibacterial activity of substituted 1,2,3,4-tetrahydropyrazino [1,2-a] indoles

  摘要：

  A series of substituted 1,2,3,4-tetrahydropyrazino [1,2-a] indole derivatives have been synthesized and tested against the Gram positive and Gram negative strains of bacteria namely Staphylococcus aureus (MTCCB 737), Salmonella typhi (MTCCB 733), Pseudomonas aeruginosa (MTCCB 741), Streptomyces thermonitrificans (MTCCB 1824) and Escherichia coli (MTCCB 1652). All synthesized compounds showed mild to moderate activity. However, compounds 4d-f were found to have potent activity against pathogenic bacteria used in the study. Their MIC ranged from 3.75 to 60 mu g/disc. In vitro toxicity tests demonstrated that toxicity of 4d-f was not significantly different than that of gentamycin. However, at higher concentration (1000-4000 mu g/ml) difference was highly significant. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.066

文献信息

• [EN] PYRAZINO[1,2-a]INDOLE COMPOUNDS, THEIR PREPARATION AND USE IN MEDICAMENTS<br/>[FR] COMPOSÉS DE PYRAZINO[1,2-A]INDOLE, LEUR PRÉPARATION ET LEUR UTILISATION DANS DES MÉDICAMENTS
  申请人：ESTEVE LABOR DR

  公开号：WO2014173903A1

  公开（公告）日：2014-10-30

  The invention refers to compounds of general formula (I) wherein the variables take the various meanings, pharmaceutical compositions containing them and their use in medicine, particularly in pain therapy.

  该发明涉及通式（I）的化合物，其中变量具有不同的含义，包括它们的制药组合物以及在医学中的使用，特别是在疼痛治疗中的应用。
• PYRAZINO[1,2-a]INDOLE COMPOUNDS, THEIR PREPARATION AND USE IN MEDICAMENTS
  申请人：LABORATORIOS DEL DR. ESTEVE, S.A.

  公开号：US20160060268A1

  公开（公告）日：2016-03-03

  The invention refers to compounds of general formula (I) wherein the variables take the various meanings, pharmaceutical compositions containing them and their use in medicine, particularly in pain therapy.

  本发明涉及通式（I）的化合物，其中变量具有不同的含义，包括这些化合物的药物组成物以及它们在医学上的应用，特别是在疼痛治疗方面。
• 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.
• PYRAZINO[1,2-A]INDOLE COMPOUNDS, THEIR PREPARATION AND USE IN MEDICAMENTS
  申请人：ESTEVE PHARMACEUTICALS, S.A.

  公开号：EP2989105B1

  公开（公告）日：2020-03-11
• US9879015B2
  申请人：——

  公开号：US9879015B2

  公开（公告）日：2018-01-30