9-(2-(1-phenylethylidene)hydrazinyl)acridine

• 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: 9-(2-(1-phenylethylidene)hydrazinyl)acridine
• 英文别名: N-(1-phenylethylideneamino)acridin-9-amine
• 化学式: C₂₁H₁₇N₃
• 分子量: 311.386
• InChiKey: KCPFAIOOYPERNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  37.28
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 盐酸 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 3.75h， 生成 9-(2-(1-phenylethylidene)hydrazinyl)acridine
  参考文献：
  名称：

  Novel 9-(2-(1-arylethylidene)hydrazinyl)acridine derivatives: Target Topoisomerase 1 and growth inhibition of HeLa cancer cells

  摘要：

  A series of 9-(2-(1-arylethylidene)hydrazinyl)acridine and its analogs were designed, synthesized and evaluated for biological activities. Various biochemical assays were performed to determine the free radical scavenging capacity of synthesized compounds (4a-4j). Anticancer activity of these compounds was assessed against two different human cancer cell lines viz cervical cancer cells (HeLa) and liver cancer cells (HepG2) as well as normal human embryonic kidney cell line (HEK 293). Compounds 4b, 4d and 4e showed potential anti-proliferative effects on HeLa cells. Based on results obtained from antioxidant and cytotoxicity studies, 4b, 4d and 4e were further studied in detail for different biological activities. 4b, 4d and 4e reduced the cell growth, inhibited metastatic activity and declined the potential of cell migration in HeLa cell lines. Topoisomerase1 (Top1) treated with compounds 4b, 4d and 4e exhibited inhibition of Top1 and prevented DNA replication. Molecular docking results validate that interaction of compounds 4b, 4d and 4e with Top1-DNA complex, which might be accountable for their inhibitory effects. Further it was concluded that compounds 4b, 4d and 4e arrests the cells at S phase and consequently induces cell death through DNA damage in HeLa cells.

  DOI：

  10.1016/j.bioorg.2019.102962

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.