3-(2-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)quinoxalin-2(1H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)quinoxalin-2(1H)-one
• 化学式: C₁₉H₁₅ClN₆O
• 分子量: 378.821
• InChiKey: TYZNQCNJYPBIKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  87.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  环戊醇 、 3-(2-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)quinoxalin-2(1H)-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以60.7%的产率得到3-(2-((5-(cyclopentyloxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)quinoxalin-2(1H)-one
  参考文献：
  名称：

  Design, synthesis and molecular docking study of novel quinoxalin-2(1H)-ones as anti-tumor active agents with inhibition of tyrosine kinase receptor and studying their cyclooxygenase-2 activity

  摘要：

  On continuation to our work, new quinoxalin-2(1H)-ones were synthesized to study their cytotoxic effect against HepG-2 and MCF-7 with their effect on the human tyrosine kinase (TRK). Compounds 12, 18, 15, 13,11a, 20 and 16, respectively, were found to be more potent than cisplatin against HepG2 and selective to TRK. Also, compounds 12, 18, 20, 13, 14, and 22, respectively, exhibited decidedly activity against MCF-7 and selectivity against human TRK compared to cisplatin. A molecular docking study was also performed to gain comprehensive understanding into plausible binding modes and to conclude the structure activity relationships of the synthesized compounds. Moreover, anti-inflammatory activity was studied. Compounds 12, 15, 18 and 22 were found to be potent and selective against COX-2. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.048
• 作为产物：
  描述：

  2,3-二羟基喹喔啉 在 溶剂黄146 、 肼 作用下， 以 乙醇 为溶剂， 生成 3-(2-((5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylene)hydrazinyl)quinoxalin-2(1H)-one
  参考文献：
  名称：

  Design, synthesis and molecular docking study of novel quinoxalin-2(1H)-ones as anti-tumor active agents with inhibition of tyrosine kinase receptor and studying their cyclooxygenase-2 activity

  摘要：

  On continuation to our work, new quinoxalin-2(1H)-ones were synthesized to study their cytotoxic effect against HepG-2 and MCF-7 with their effect on the human tyrosine kinase (TRK). Compounds 12, 18, 15, 13,11a, 20 and 16, respectively, were found to be more potent than cisplatin against HepG2 and selective to TRK. Also, compounds 12, 18, 20, 13, 14, and 22, respectively, exhibited decidedly activity against MCF-7 and selectivity against human TRK compared to cisplatin. A molecular docking study was also performed to gain comprehensive understanding into plausible binding modes and to conclude the structure activity relationships of the synthesized compounds. Moreover, anti-inflammatory activity was studied. Compounds 12, 15, 18 and 22 were found to be potent and selective against COX-2. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.048