2-(4-methoxyphenyl)-2,10-dihydro-3H-benzo[6,7]oxepino[3,4-c]pyrazol-3-one | 1583273-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 2-(4-methoxyphenyl)-2,10-dihydro-3H-benzo[6,7]oxepino[3,4-c]pyrazol-3-one
• 英文别名: 2-(4-methoxyphenyl)-4H-[1]benzoxepino[3,4-c]pyrazol-1-one
• CAS: 1583273-07-7
• 化学式: C₁₈H₁₄N₂O₃
• 分子量: 306.321
• InChiKey: LMGYFXGYPVRVQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-(chloromethyl)-2-hydroxy-2H-chromene-3-carboxylate 在 溶剂黄146 、 乙氧甲酰基亚乙基三苯基 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-(4-methoxyphenyl)-2,10-dihydro-3H-benzo[6,7]oxepino[3,4-c]pyrazol-3-one
  参考文献：
  名称：

  Convenient one-pot synthesis, anti-mycobacterial and anticancer activities of novel benzoxepinoisoxazolones and pyrazolones

  摘要：

  Series of new benzoxepinoisoxazolones 4a-d and pyrazolones 6a-t were prepared by the cyclocondensation of substituted (E)-ethyl 3-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates 3a-d with hydroxylamine hydrochloride and phenylhydrazine hydrochlorides 5a-k. Synthesized compounds were screened for their in vitro anti-mycobacterial activity and anticancer activity. Ten compounds displayed good anti-mycobacterial activity, among these; compound 4d and 6b found to be potent when compared to standard drug isoniazid. Eleven compounds displayed good anticancer activity and compounds 4b-d displayed equipotent activity on HeLa cell lines when compared to standard drug doxorubicin. Activation of caspase-3 and caspase-9 has been measured for compounds 4b-d on HeLa cell lines (apoptosis). This is the first report assigning in vitro anti-mycobacterial, anticancer and structure-activity relationship for this new class of benzoxepinoisoxazolones and pyrazolones. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.042