10-Chloro-7H-indolo(2,3-c)isoquinoline-5(6H)-one | 73165-95-4

• 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: 10-Chloro-7H-indolo(2,3-c)isoquinoline-5(6H)-one
• 英文别名: 10-Chlor-7H-indolo<2,3-c>isochinolin-5(6H)-on；10-Chlor-7H-indolo[2,3-c]isochinolin-5(6H)-on；10-Chloro-6,7-dihydroindolo[2,3-c]isoquinolin-5-one
• CAS: 73165-95-4
• 化学式: C₁₅H₉ClN₂O
• 分子量: 268.702
• InChiKey: IWMACMXCFUYEJG-UHFFFAOYSA-N

物化性质

• 熔点：
  >350 °C
• 沸点：
  431.1±25.0 °C(Predicted)
• 密度：
  1.468±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  10-Chloro-7H-indolo(2,3-c)isoquinoline-5(6H)-one 在 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2'-[10-chloro-6H,7H-indolo[2,3-c]isoquinolin-5-one-6-yl]-1',3',4'-oxadiazole-5'-thione
  参考文献：
  名称：

  Synthesis of some new indolo[2,3-c]isoquinolinyl pyrazoles, -1,3,4-oxadiazoles and their biological activities

  摘要：

  A new series of novel compounds [10-substituted 6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]carbohydrazides (3a-c), 1-[10-substituted 6H, 7H-indolo[2,3-c]isoquinolin-5-one-6-yl]fomyl-, -3',5'-dimethylpyrazoles (4a-c), -3',5'-diphenylpyrazoles (5a-c), -3'-methylpyrazol-5'-ones (6a-c) and -1',3',4'-oxidiazole-2'-thiones (7a-c) linked to indoloisoquinoline at position-6 through formyl bridge was prepared. The structures of these newly synthesized compounds were confirmed by their spectral studies and elemental analysis. These compounds have been screened for their antimicrobial and antioxidant activities. Compounds 4a, 4b, 5a, 5b, 5c, 6b, 7a, and 7c exhibited the maximum zone of inhibition against A. niger, A. flavus, and A. fumigatus. Compounds 4a, 5a, 5c, 6b, 6c, 7a, and 7b showed good antibacterial activity. Compounds 4b, 4c, 5b, 5c, 6a, 6b, 7a, 7b, and 7c showed good radical scavenging activity compared with standards.

  DOI：

  10.1007/s00044-012-0366-6
• 作为产物：
  描述：

  5-chloro-3-phenyl-1H-indol-2-carbonyl azide 以 二苯醚 为溶剂， 反应 4.0h， 生成 10-Chloro-7H-indolo(2,3-c)isoquinoline-5(6H)-one
  参考文献：
  名称：

  探索吲哚[3,2c] 异喹啉衍生三唑作为潜在抗菌剂和 DNA 裂解剂：合成、DFT 计算和分子模型研究

  摘要：

  吲哚及其衍生物是药物设计和开发中众所周知的混合基序。我们在这里报道了新的 9-chloro-1-(4-substituted phenyl)-12 H -indolo[2,3-c][1,2,4]triazolo[3,4-a]isoquinolines 7 (ah )。通过使用红外、核磁共振和质谱等光谱技术确认了新合成化合物的结构。使用具有 6-31+g(d) 全电子基础的 CAM-B3LYP 混合功能对所选分子进行了 DFT 计算使用 Gaussian 09 包设置。描述了合成衍生物的药物相似性预测。报告了所有化合物7 (ah)的体外抗微生物和 DNA 裂解活性。化合物7a、7b和与标准药物相比，7h显示出出色的微生物抑制和 DNA 切割活性。此外，通过Auto dock软件对新合成的分子进行了对接研究，两个分子靶点表皮生长因子受体酪氨酸激酶（1M17）和C-kit酪氨酸激酶（1T46）表

  DOI：

  10.1016/j.bioorg.2023.106598

文献信息

• Hiremath, Shiva Yogi P.; Badami, Prema S.; Purohit, Muralidhar G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 1235 - 1238
  作者：Hiremath, Shiva Yogi P.、Badami, Prema S.、Purohit, Muralidhar G.

  DOI：——

  日期：——
• Synthesis and biological evaluation of novel indolo[2,3-c]isoquinoline derivatives
  作者：Anand R. Saundane、R. Kalpana

  DOI：10.1007/s00044-014-1243-2

  日期：2015.4

  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.
• HIREMATH SHIVAYOGI; BADAMI PREMA (SMT); PUROHIT MURALIDHAR G., INDIAN J. CHEM., 24,(1985) N 12, 1235-1238
  作者：HIREMATH SHIVAYOGI、 BADAMI PREMA (SMT)、 PUROHIT MURALIDHAR G.

  DOI：——

  日期：——
• MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES
  申请人：Merck Patent GmbH

  公开号：US20220216424A1

  公开（公告）日：2022-07-07

  The invention relates to compounds which are suitable for use in electronic devices, and to electronic devices, in particular organic electroluminescent devices, containing said compounds.
• US4263304A
  申请人：——

  公开号：US4263304A

  公开（公告）日：1981-04-21