3-acetyl-7-chloro-6-fluorocinnolin-4(1H)-one | 851218-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-acetyl-7-chloro-6-fluorocinnolin-4(1H)-one
• 英文别名: 3-acetyl-7-chloro-6-fluoro-1H-cinnolin-4-one
• CAS: 851218-42-3
• 化学式: C₁₀H₆ClFN₂O₂
• 分子量: 240.621
• InChiKey: AVYODQSUEKIAHF-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225 °C(Solv: methanol (67-56-1))
• 沸点：
  395.4±52.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetyl-7-chloro-6-fluorocinnolin-4(1H)-one 、 对甲氧基苯甲酰肼 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以60%的产率得到(7-Chloro-8-fluoro-3-methylpyrazolo[4,3-c]cinnolin-1-yl)-(4-methoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of pyrazolo[4,3-c]cinnoline derivatives as potential anti-inflammatory and antibacterial agents

  摘要：

  A series of pyrazolo[4,3-c]cinnoline derivatives was synthesized, characterized and evaluated for anti-inflammatory and antibacterial activity. Test compounds that exhibited good anti-inflammatory activity were further screened for their ulcerogenic and lipid peroxidation activity. Compounds 4d and 41 showed promising anti-inflammatory activity with reduced ulcerogenic and lipid peroxidation activity when compared to naproxen. Docking results of these two compounds with COX-2 (PDB ID: 1CX2) also exhibited a strong binding profile. Among the test derivatives, compound 4i displayed significant antibacterial property against gram-negative (Escherichia coli and Pseudomonas aeruginosa) and gram-positive (Staphylococcus aureus) bacteria. However, compound 4b emerged as the best dual anti-inflammatory antibacterial agent in the present study. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.045
• 作为产物：
  描述：

  ethyl-2-[2-(3-chloro-4-fluorophenyl)hydrazinylidene]-3-oxobutanoate 在 aluminum (III) chloride 、 盐酸 、 水 作用下， 以 氯苯 为溶剂， 反应 16.0h， 以76%的产率得到3-acetyl-7-chloro-6-fluorocinnolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of pyrazolo[4,3-c]cinnoline derivatives as potential anti-inflammatory and antibacterial agents

  摘要：

  A series of pyrazolo[4,3-c]cinnoline derivatives was synthesized, characterized and evaluated for anti-inflammatory and antibacterial activity. Test compounds that exhibited good anti-inflammatory activity were further screened for their ulcerogenic and lipid peroxidation activity. Compounds 4d and 41 showed promising anti-inflammatory activity with reduced ulcerogenic and lipid peroxidation activity when compared to naproxen. Docking results of these two compounds with COX-2 (PDB ID: 1CX2) also exhibited a strong binding profile. Among the test derivatives, compound 4i displayed significant antibacterial property against gram-negative (Escherichia coli and Pseudomonas aeruginosa) and gram-positive (Staphylococcus aureus) bacteria. However, compound 4b emerged as the best dual anti-inflammatory antibacterial agent in the present study. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.045

文献信息

• Synthesis and pharmacological evaluation of pyrazolo[4,3-c]cinnoline derivatives as potential anti-inflammatory and antibacterial agents
  作者：Rajiv Kumar Tonk、Sandhya Bawa、Gita Chawla、Girdhar Singh Deora、Suresh Kumar、Vandana Rathore、Naveen Mulakayala、Azad Rajaram、Arunasree M. Kalle、Obaid Afzal

  DOI：10.1016/j.ejmech.2012.08.045

  日期：2012.11

  A series of pyrazolo[4,3-c]cinnoline derivatives was synthesized, characterized and evaluated for anti-inflammatory and antibacterial activity. Test compounds that exhibited good anti-inflammatory activity were further screened for their ulcerogenic and lipid peroxidation activity. Compounds 4d and 41 showed promising anti-inflammatory activity with reduced ulcerogenic and lipid peroxidation activity when compared to naproxen. Docking results of these two compounds with COX-2 (PDB ID: 1CX2) also exhibited a strong binding profile. Among the test derivatives, compound 4i displayed significant antibacterial property against gram-negative (Escherichia coli and Pseudomonas aeruginosa) and gram-positive (Staphylococcus aureus) bacteria. However, compound 4b emerged as the best dual anti-inflammatory antibacterial agent in the present study. (C) 2012 Elsevier Masson SAS. All rights reserved.