N'-{[(phenyl)methylidene]-2-(quinolin-8-yloxy)}acetohydrazide | 42322-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N'-{[(phenyl)methylidene]-2-(quinolin-8-yloxy)}acetohydrazide
• 英文别名: (quinolin-8-yloxy)acetic acid benzylidenehydrazone；quinolin-8-yloxy-acetic acid benzylidenehydrazide
• CAS: 42322-33-8
• 化学式: C₁₈H₁₅N₃O₂
• 分子量: 305.336
• InChiKey: LSFDDZISPVRAKG-UHFFFAOYSA-N

物化性质

• 熔点：
  105 °C(Solv: methanol (67-56-1))
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.58
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N'-{[(phenyl)methylidene]-2-(quinolin-8-yloxy)}acetohydrazide 在 吡啶 作用下， 以 乙醇 、 苯 为溶剂， 反应 12.0h， 生成 N'-[2-phenyl-3-N-ethoxyphthalimido-5-oxoimidazolidin-1-yl]-2-(quinolin-8-yloxy)acetamide
  参考文献：
  名称：

  Bhambi, Dinesh; Sain, Devendra K.; Salvi, Vijay K., Journal of the Indian Chemical Society, 2009, vol. 86, # 10, p. 1072 - 1078

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-(quinolin-8-yloxy)acetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 N'-{[(phenyl)methylidene]-2-(quinolin-8-yloxy)}acetohydrazide
  参考文献：
  名称：

  Design and synthesis of conjugated azo-hydrazone analogues using nano BF3·SiO2 targeting ROS homeostasis in oncogenic and vascular progression

  摘要：

  Disrupted redox balance is implicated in multiple pathologies including malignant progression and tumor angiogenesis. In this investigation, we report the design and development of novel and effective ROS detoxifying azo-hydrazone molecules targeting malignant pathologies and neoangiogenesis. A series of azo-derivatives conjugated to hydrazones moieties (9a-j) were synthesized using Nano BF3 center dot SiO2. The compounds (9a-j) were screened for in-vitro antioxidant and lipid peroxidation inhibitory activity. Among the series 9a-j, compound 9f potently quenched biologically relevant radicals such as superoxide and hydrogen peroxide which emerged as the lead ROS detoxifying molecules. Compound 9f potently inhibited the proliferative capability of Daltons Lymphoma Ascites (DLA) tumor cells in-vivo in dose dependent manner. Regressed tumor progression was correlated with pronounced endogenous antioxidant enzyme superoxide dismutase and catalase in-vivo. Also, ROS levels were severely suppressed in 9f treated mice as assessed by lapsed lipid peroxidation. Altered enzymic and ROS levels in-vivo by 9f were implicated in suppressed VEGF secretion leading to regressed tumor neo-vasculature and tumor growth. Considering together, it is evident that the synthetic azo-hydrazone analogue 9f with potent ROS scavenging efficacy inhibits tumor progression and neo-angiogenesis.

  DOI：

  10.1016/j.biopha.2017.08.076