1-phenyl-2-oxo-3-chloro-1,2-dihydropyrrolo<2,3-b>quinoxaline | 125849-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-phenyl-2-oxo-3-chloro-1,2-dihydropyrrolo<2,3-b>quinoxaline
• 英文别名: 3-chloro-1-phenyl-1H,4H-pyrrolo[2,3,b]quinoxaline-2-one；3-chloro-1-phenyl-1,4-dihydro-2H-pyrrolo[2,3-b]quinoxalin-2-one；1-Phenyl-3-chloropyrrolo<2,3-b>chinoxalin-2(4H)-on；3-chloro-1-phenyl-1,4-dihydro-pyrrolo[2,3-b]quinoxalin-2-one；3-chloro-1-phenyl-4H-pyrrolo[3,2-b]quinoxalin-2-one
• CAS: 125849-52-7
• 化学式: C₁₆H₁₀ClN₃O
• 分子量: 295.728
• InChiKey: VIMVXDGZOYEQCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.68
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  苯胺 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 1-phenyl-2-oxo-3-chloro-1,2-dihydropyrrolo<2,3-b>quinoxaline
  参考文献：
  名称：

  A new class of pyrrolo[2,3-b]quinoxalines: synthesis, anticancer and antimicrobial activities

  摘要：

  A series of 3-chloro-1-aryl-4-dihydro-2H-pyrrolo[2,3-b]quinoxalin-2-ones and 3-chloro-1-aryl-6,7-dimethyl-1,4-dihydro-2H-pyrrolo[2,3-b]quinoxalin-2-ones was prepared by the condensation of o-phenylenediamine or 4,5-dimethyl-1,2-aminobenzene with N-aryl-3,4-dichloro-maleimides. All the prepared quinoxalines were tested for their antitumor activity against three human cancer cell lines (prostate cells PC3, colorectal cells Caco-2, and cervical cells HeLa), and a mammalian cell line (Vero cells). The compounds were also tested for their antibacterial properties against three different bacterial cells Escherichia coli, Bacillus spizizenii, and Pseudomonas aeruginosa. The compounds 3c, 3d, 3g, 3h, 3i and 4a, 4b, 4h showed anti-proliferative activity against the tested cell lines. Regarding their antibacterial activity, compounds 3a, 3g, 4a, and 4h showed inhibitory activity against E. coli, and B. spizizenii only.

  DOI：

  10.1515/znb-2023-0050

文献信息

• Katritzky, Alan R.; Fan, Wei-Qiang; Li, Qiao-Ling, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 885 - 892
  作者：Katritzky, Alan R.、Fan, Wei-Qiang、Li, Qiao-Ling、Bayyuk, Shibli

  DOI：——

  日期：——
• Some synthetic applications of 2,3-Dichloro-N-phenylmaleimide: A novel synthesis of 2-phenylpyrrolo[3,4-b]quinoxaline-1,3-diones. I
  作者：Leila Hanaineh-Abdelnour、Shibly Bayyuk、Rima Theodorie

  DOI：10.1016/s0040-4020(99)00672-9

  日期：1999.10

  2,3-Dichloro-N-phenylmaleimide 2 undergoes nucleophilic substitution reactions by a variety of nucleophiles giving either monosubstituted 5 or disubstituted 3 products. Treatment of 5 with sodium azide at room temperature results in cyclization to the corresponding 2-phenylpyrrolo[3,4-b]quinoxaline-1,3-diones 6, while at higher temperatures 5 is reduced to the 2-amino-3-amino-N-phenylmaleimides 7. (C) 1999 Elsevier Science Ltd. All rights reserved.
• KATRIZKY, ALAN R.;FAN, WEI-QIANG;LI, QIAO-LING;BAYYUK, SHIBLI, J. HETEROCYCL. CHEM., 26,(1989) N, C. 885-892
  作者：KATRIZKY, ALAN R.、FAN, WEI-QIANG、LI, QIAO-LING、BAYYUK, SHIBLI

  DOI：——

  日期：——
• A new class of pyrrolo[2,3-<i>b</i>]quinoxalines: synthesis, anticancer and antimicrobial activities
  作者：Bader A. Salameh、Eman H. Al-Hushki、Wamidh H. Talib、Raed Ghanem、Fatima-Azzahra Delmani、Asma I. Mahmod

  DOI：10.1515/znb-2023-0050

  日期：——

  A series of 3-chloro-1-aryl-4-dihydro-2H-pyrrolo[2,3-b]quinoxalin-2-ones and 3-chloro-1-aryl-6,7-dimethyl-1,4-dihydro-2H-pyrrolo[2,3-b]quinoxalin-2-ones was prepared by the condensation of o-phenylenediamine or 4,5-dimethyl-1,2-aminobenzene with N-aryl-3,4-dichloro-maleimides. All the prepared quinoxalines were tested for their antitumor activity against three human cancer cell lines (prostate cells PC3, colorectal cells Caco-2, and cervical cells HeLa), and a mammalian cell line (Vero cells). The compounds were also tested for their antibacterial properties against three different bacterial cells Escherichia coli, Bacillus spizizenii, and Pseudomonas aeruginosa. The compounds 3c, 3d, 3g, 3h, 3i and 4a, 4b, 4h showed anti-proliferative activity against the tested cell lines. Regarding their antibacterial activity, compounds 3a, 3g, 4a, and 4h showed inhibitory activity against E. coli, and B. spizizenii only.