N'-(anthracen-9-ylmethylene)nicotinohydrazide | 89552-82-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N'-(anthracen-9-ylmethylene)nicotinohydrazide
• 英文别名: N-(anthracen-9-ylmethylideneamino)pyridine-3-carboxamide
• CAS: 89552-82-9
• 化学式: C₂₁H₁₅N₃O
• mdl: MFCD00517885
• 分子量: 325.37
• InChiKey: HNGMCZQRNYTXMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-吡啶甲酰肼 、 9-蒽甲醛 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.5h， 以83%的产率得到N'-(anthracen-9-ylmethylene)nicotinohydrazide
  参考文献：
  名称：

  Novel Carbohydrazide and Hydrazone Biomarkers Based on 9-Substituted Acridine and Anthracene Fluorogens

  摘要：

  Three series of carbohydrazides or hydrazones bearing either acridine or anthracene pharmacophores were synthesized as potential noncovalent DNA-binding antitumor agents. Carbohydrazides with an acridine or anthracene moiety were prepared from appropriate acridine or anthracene carbaldehydes via cyclocondensation with selected hydrazides whilst hydrazones with a 10H-acridin-9-ylidene moiety were obtained by condensation of (acridin-9-yl)hydrazine with various aldehydes or ketones. The spectroscopic properties of the first two series revealed efficient fluorescence implying that the compounds could be amenable for use as biomarkers. The structures of the compounds were characterized by spectral methods (UV-vis, fluorescence, IR, and (1)H, (13)C, and 2D NMR) and quantum-chemical calculations (DFT, ZINDO, and AM I). The first carbohydrazide series was also tested against human leukemia cell line HL-60 wherein the phenyl-substituted derivative was found to possess the highest activity.

  DOI：

  10.3987/com-09-s(s)83

文献信息

• Novel Carbohydrazide and Hydrazone Biomarkers Based on 9-Substituted Acridine and Anthracene Fluorogens
  作者：Ján Imrich、Zdenka Bedlovičová、Pavol Kristian、Ivan Danihel、Stanislav Böhm、Danica Sabolová、Mária Kožurková、Helena Paulíková、Karel D. Klika

  DOI：10.3987/com-09-s(s)83

  日期：——

  Three series of carbohydrazides or hydrazones bearing either acridine or anthracene pharmacophores were synthesized as potential noncovalent DNA-binding antitumor agents. Carbohydrazides with an acridine or anthracene moiety were prepared from appropriate acridine or anthracene carbaldehydes via cyclocondensation with selected hydrazides whilst hydrazones with a 10H-acridin-9-ylidene moiety were obtained by condensation of (acridin-9-yl)hydrazine with various aldehydes or ketones. The spectroscopic properties of the first two series revealed efficient fluorescence implying that the compounds could be amenable for use as biomarkers. The structures of the compounds were characterized by spectral methods (UV-vis, fluorescence, IR, and (1)H, (13)C, and 2D NMR) and quantum-chemical calculations (DFT, ZINDO, and AM I). The first carbohydrazide series was also tested against human leukemia cell line HL-60 wherein the phenyl-substituted derivative was found to possess the highest activity.