3-hydroxy-4-methoxy-benzaldehyde-(2,4-dinitro-phenylhydrazone) | 1166-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-hydroxy-4-methoxy-benzaldehyde-(2,4-dinitro-phenylhydrazone)
• 英文别名: 3-Hydroxy-4-methoxy-benzaldehyd-(2,4-dinitro-phenylhydrazon)；Isovanillin-<2,4-dinitro-phenylhydrazon>；Isovanillin-2,4-dinitrophenylhydrazon；5-[[(2,4-Dinitrophenyl)hydrazinylidene]methyl]-2-methoxyphenol
• CAS: 1166-14-9
• 化学式: C₁₄H₁₂N₄O₆
• 分子量: 332.272
• InChiKey: NLGSYZHLKMBOTB-UHFFFAOYSA-N

物化性质

• 沸点：
  540.2±50.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 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：
  146
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  异香兰素 、 2,4-二硝基苯肼 以 乙醇 为溶剂， 反应 24.0h， 以78%的产率得到3-hydroxy-4-methoxy-benzaldehyde-(2,4-dinitro-phenylhydrazone)
  参考文献：
  名称：

  In vitro and in vivo anti-inflammatory properties of imine resveratrol analogues

  摘要：

  Resveratrol is a natural polyphenol found mainly on red grapes and in red wine, pointed as an important antiinflammatory/immunomodulatory molecule. However, its bioavailability problems have limited its use encouraging the search for new alternatives agents. Thus, in this study, we synthesize 12 resveratrol analogues (6 imines, 1 thioimine and 5 hydrazones) and investigated its cytotoxicity, antioxidant activity and in vitro antiinflammatory/immunomodulatory properties. The most promising compounds were also evaluated in vivo. The results showed that imines presented less cytotoxicity, were more effective than resveratrol on DPPH scavenger and exhibited an anti-inflammatory profile. Among them, the imines with a radical in the para position, on the ring B, not engaged in an intramolecular hydrogen-interaction, showed more prominent anti-inflammatory activity modulating, in vivo, the edema formation, the inflammatory infiltration and cytokine levels. An immunomodulatory activity also was observed in these molecules. Thus, our results suggest that imines with these characteristics presents potential to control inflammatory disorders.

  DOI：

  10.1016/j.bmc.2018.08.029

文献信息

• In vitro and in vivo anti-inflammatory properties of imine resveratrol analogues
  作者：Danielle Cristina Zimmermann-Franco、Bruna Esteves、Leticia Moroni Lacerda、Isabela de Oliveira Souza、Juliana Alves dos Santos、Nícolas de Castro Campos Pinto、Elita Scio、Adilson David da Silva、Gilson Costa Macedo

  DOI：10.1016/j.bmc.2018.08.029

  日期：2018.9

  Resveratrol is a natural polyphenol found mainly on red grapes and in red wine, pointed as an important antiinflammatory/immunomodulatory molecule. However, its bioavailability problems have limited its use encouraging the search for new alternatives agents. Thus, in this study, we synthesize 12 resveratrol analogues (6 imines, 1 thioimine and 5 hydrazones) and investigated its cytotoxicity, antioxidant activity and in vitro antiinflammatory/immunomodulatory properties. The most promising compounds were also evaluated in vivo. The results showed that imines presented less cytotoxicity, were more effective than resveratrol on DPPH scavenger and exhibited an anti-inflammatory profile. Among them, the imines with a radical in the para position, on the ring B, not engaged in an intramolecular hydrogen-interaction, showed more prominent anti-inflammatory activity modulating, in vivo, the edema formation, the inflammatory infiltration and cytokine levels. An immunomodulatory activity also was observed in these molecules. Thus, our results suggest that imines with these characteristics presents potential to control inflammatory disorders.