5-hydrazino-10-methyl-7H-indolo[2,3-c]isoquinoline | 439574-04-6

• 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: 5-hydrazino-10-methyl-7H-indolo[2,3-c]isoquinoline
• CAS: 439574-04-6
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: MLIDONOKDICXNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.73
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-hydrazino-10-methyl-7H-indolo[2,3-c]isoquinoline 以 乙醇 为溶剂， 反应 10.0h， 生成 3,3a-dihydro-2-(10-methyl-7H-indolo[2,3-c]isoquinolin-5-yl)-2H-pyrazolo[ 3,4-d]pyrimidin-4(5H)-one
  参考文献：
  名称：

  新型吲哚[2,3-c]异喹啉类似物的DFT、PM6的设计、合成、探索、与SAR-CoV-2 Mpro的分子对接以及抗癌特性

  摘要：

  成功合成了一系列新型吲哚并[2,3-c]异喹啉衍生物，与带有取代Cl、OCH、CH和H基团II、II(a-d)的吡唑和吡唑并[3,4-d]嘧啶酮环偶联，表现出显着的生物学和药理学相关性。通过 MOPAC 软件使用半经验方法 PM6 进行计算化学来研究它们的热化学性质。化合物表现出较低的热形成（ΔHf）值68.89873 kcal/摩尔，表明稳定性增强，而化合物表现出较高的ΔHf值151.32004 kcal/摩尔，表明稳定性较低。 B3LYP/def2-TZVP def2/J 的密度泛函理论 (DFT) 用于分析电子结构和几何优化。 HOMO-LUMO能隙(ΔEg)在嘧啶酮>吡唑系列中由高到低排列，能隙最低(ΔEg = 2.994 eV)，最高(ΔEg = 3.433 eV)。化合物显示出最高的亲电指数 (χ = 3.540 eV)，并表现出有效的抗癌活性，如在衍生物和化合物中观察到的那样，并证明与

  DOI：

  10.1016/j.molstruc.2024.138268
• 作为产物：
  描述：

  10-methyl-6H,7H-indolo[2,3-c]isoquinoline-5-thione 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-hydrazino-10-methyl-7H-indolo[2,3-c]isoquinoline
  参考文献：
  名称：

  Synthesis and biological evaluation of novel indolo[2,3-c]isoquinoline derivatives

  摘要：

  A new series of novel compounds 1-tert-butyl-9-substituted-12H-indolo[2,3-c]isoquinolino[5,6-c]-1,2,4-triazoles (4a-4c), 10-substituted-2-phenyl-1,13-dihydroindolo[2,3-c]isoquinolino[5,6-c]-1,2,4-triazines (5a-5l), 2-(10-substituted-7H-indolo[2,3-c]isoquinolin-5-yl)-4-phenylphthalazin-1-ones (6a-6c), 2-[2-(10-substituted-7H-indolo[2,3-c]isoquinolinyl)hydrazinecarbonyl]benzoic acid (7a-7c), and 2-(10-substituted-7H-indolo[2,3-c]isoquinolin-5-yl)phthalazine-1,4-diones (8a-8c) were synthesized. The structures of these newly synthesized compounds were confirmed by their spectral studies and elemental analysis. These compounds have been screened for their antimicrobial, antitubercular, antioxidant, and cytotoxic activities. Compounds 4b, 5a, 5g, 5h, 6a, 6b, and 7b exhibited the maximum zone of inhibition against Staphylococcus aureus. Compounds 5d and 6c exhibited the maximum zone of inhibition against Pseudomonas aeruginosa. Compounds 7a and 8c showed maximum zone of inhibition against Aspergillus niger. Compounds 5k and 8c showed maximum zone of inhibition against Aspergillus flavus. Compounds 4a (MIC-1.6 A mu g/ml) and 5 h (MIC-0.2 A mu g/ml) exhibited promising antitubercular activity against Mycobacterium tuberculosis H37Rv strain. Compounds 4b, 4c, 5a, 5c, 5e, 5h, 6a, 6b, 6c, 8a, and 8b exhibited good radical scavenging activity compared with standards. Compounds 4b, 4c, 5a, 5c, 5g, 6a, and 8b exhibited maximum reducing ability. Compounds 4a and 5h exhibited 100 % cell lysis at concentration 10 A mu g/ml.

  DOI：

  10.1007/s00044-014-1243-2

文献信息

• Hiremath; Rudresh; Saundane, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 2, p. 394 - 399
  作者：Hiremath、Rudresh、Saundane

  DOI：——

  日期：——