2-(4-chlorophenyl)-2-(hydroxyimino)-1-(4-methoxyphenyl)ethanone | 42416-70-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-chlorophenyl)-2-(hydroxyimino)-1-(4-methoxyphenyl)ethanone
• 英文别名: 4-Chlor-4'-methoxy-α-oximino-desoxybenzoin；2-(4-chlorophenyl)-2-hydroxyimino-1-(4-methoxyphenyl)ethanone
• CAS: 42416-70-6
• 化学式: C₁₅H₁₂ClNO₃
• 分子量: 289.718
• InChiKey: XXDZEVAQMDSBRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-2-(hydroxyimino)-1-(4-methoxyphenyl)ethanone 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成 ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-1,2,4-triazine-3-ylthio)acetate
  参考文献：
  名称：

  Synthesis and neuroprotective activity of novel 1,2,4-triazine derivatives with ethyl acetate moiety against H 2 O2 and Aβ-induced neurotoxicity

  摘要：

  A series of 5,6-diaryl-1,2,4-triazine-3-thioacetate derivatives 3a-f, 8a-d and their regioisomer 8e were synthesized. Neuroprotective activity of compounds was assessed against H2O2 and beta-amyloid-induced toxicity in PC12 and SH-SY5Y cells respectively. Surprisingly, ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-3-thioxo-1,2,4-triazin-2(3H)-yl)acetate (8e) was the most potent compound in both tests with EC50 of 14 mu M in H2O2 induced apoptosis and also could increase 40% of cell viability revealed by cytometric analysis with Annexin V/PI staining. It was also shown that regioisomer 8e has more neuroprotective activity than Quercetin in beta-amyloid induced toxicity. Morphologic evaluation of cells by DAPI staining and TUNEL assay showed the effectiveness of this compound to improve neurite outgrowth in neuronal cells.

  DOI：

  10.1007/s00044-017-2003-x
• 作为产物：
  描述：

  对氯苯乙酸 在 磷酸 、 sodium 、 三氟乙酸酐 作用下， 以 甲醇 为溶剂， 反应 0.66h， 生成 2-(4-chlorophenyl)-2-(hydroxyimino)-1-(4-methoxyphenyl)ethanone
  参考文献：
  名称：

  Synthesis and neuroprotective activity of novel 1,2,4-triazine derivatives with ethyl acetate moiety against H 2 O2 and Aβ-induced neurotoxicity

  摘要：

  A series of 5,6-diaryl-1,2,4-triazine-3-thioacetate derivatives 3a-f, 8a-d and their regioisomer 8e were synthesized. Neuroprotective activity of compounds was assessed against H2O2 and beta-amyloid-induced toxicity in PC12 and SH-SY5Y cells respectively. Surprisingly, ethyl 2-(5-(4-chlorophenyl)-6-(4-methoxyphenyl)-3-thioxo-1,2,4-triazin-2(3H)-yl)acetate (8e) was the most potent compound in both tests with EC50 of 14 mu M in H2O2 induced apoptosis and also could increase 40% of cell viability revealed by cytometric analysis with Annexin V/PI staining. It was also shown that regioisomer 8e has more neuroprotective activity than Quercetin in beta-amyloid induced toxicity. Morphologic evaluation of cells by DAPI staining and TUNEL assay showed the effectiveness of this compound to improve neurite outgrowth in neuronal cells.

  DOI：

  10.1007/s00044-017-2003-x