(E)-4-((2-(phthalazin-1-yl)hydrazono)methyl)benzene-1,2-diol hydrochloride | 1621252-60-5

• 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: (E)-4-((2-(phthalazin-1-yl)hydrazono)methyl)benzene-1,2-diol hydrochloride
• 英文别名: 4-[(E)-(phthalazin-1-ylhydrazinylidene)methyl]benzene-1,2-diol;hydrochloride
• CAS: 1621252-60-5
• 化学式: C₁₅H₁₂N₄O₂*ClH
• 分子量: 316.747
• InChiKey: DBQURJZZXRIEJA-OHGISNTKSA-N

物化性质

• 熔点：
  >280 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.6
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  盐酸肼屈嗪 、 3,4-二羟基苯甲醛 以 乙醇 为溶剂， 以81%的产率得到(E)-4-((2-(phthalazin-1-yl)hydrazono)methyl)benzene-1,2-diol hydrochloride
  参考文献：
  名称：

  Synthesis, antioxidant and cytoprotective evaluation of potential antiatherogenic phenolic hydrazones. A structure–activity relationship insight

  摘要：

  A novel series of hydrazones derived from substituted benzaldehydes have been synthesized as potential antiatherogenic agents. Several methods were used for exploring their antioxidant and cytoprotective properties, such as their scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, the inhibition of superoxide anion (O₂(·-)) generation and the measurement of cell-induced low-density lipoprotein oxidation (monitored by the formation of TBARS). The cytoprotective efficacy was also evaluated by measuring the cell viability (monitored by the MTT assay) in the presence of cytotoxic oxidized LDL. In this report, we discuss the relationship between the chemical structure of phenolic hydrazones and their antioxidant and cytoprotective activities, for subsequent application as antiatherogenic agents. This SAR study confirms that the phenolic frame is not the only prerequisite for antioxidant activity and N-methylbenzothiazole hydrazone moiety magnifies the dual required properties in two most interesting derivatives.

  DOI：

  10.1016/j.bmc.2014.05.034

文献信息

• Synthesis, antioxidant and cytoprotective evaluation of potential antiatherogenic phenolic hydrazones. A structure–activity relationship insight
  作者：Corinne Vanucci-Bacqué、Chantal Carayon、Corinne Bernis、Caroline Camare、Anne Nègre-Salvayre、Florence Bedos-Belval、Michel Baltas

  DOI：10.1016/j.bmc.2014.05.034

  日期：2014.8

  A novel series of hydrazones derived from substituted benzaldehydes have been synthesized as potential antiatherogenic agents. Several methods were used for exploring their antioxidant and cytoprotective properties, such as their scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, the inhibition of superoxide anion (O₂(·-)) generation and the measurement of cell-induced low-density lipoprotein oxidation (monitored by the formation of TBARS). The cytoprotective efficacy was also evaluated by measuring the cell viability (monitored by the MTT assay) in the presence of cytotoxic oxidized LDL. In this report, we discuss the relationship between the chemical structure of phenolic hydrazones and their antioxidant and cytoprotective activities, for subsequent application as antiatherogenic agents. This SAR study confirms that the phenolic frame is not the only prerequisite for antioxidant activity and N-methylbenzothiazole hydrazone moiety magnifies the dual required properties in two most interesting derivatives.