4-(1-(4-nitrophenyl)-1H-pyrazol-4-yl)pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1-(4-nitrophenyl)-1H-pyrazol-4-yl)pyridine
• 化学式: C₁₄H₁₀N₄O₂
• 分子量: 266.259
• InChiKey: SUKBXICEXFBKHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.85
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  吡啶-4-乙酸 在 hydrazine hydrate 、 potassium tert-butylate 、 sodium hydroxide 、 三氯氧磷 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 7.25h， 生成 4-(1-(4-nitrophenyl)-1H-pyrazol-4-yl)pyridine
  参考文献：
  名称：

  Design, synthesis, and biologic evaluation of some novel N-arylpyrazole derivatives as cytotoxic agents

  摘要：

  A novel series of N-arylpyrazole derivatives (5a-5d, 7a-7c) has been designed and synthesized via aromatic substitution reaction of N-nonsubstituted pyrazoles with 4-fluoronitrobenzene in the presence of base. The structures of these compounds were established on the basis of elemental (C, H, and N) and spectral analysis (H-1 NMR, C-13 NMR, HRMS, and FT-IR). All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines: carcinoma (Bel-7402), nasopharyngeal carcinoma (KB), immature granulocyte leukemia (HL-60), and gastrocarcinoma (BGC-823) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The results showed that most of the obtained compounds exhibited promising cytotoxicity against tested carcinoma cell lines with low IC50 values. The bis-pyrazole derivative 7c, bearing alkoxy group on the 5-position of phenyl ring, was the most effective one. It is inhibition of cell growth of Bel-7402 cells was 1.5-fold higher than that found for cisplatin. And, also mono-pyrazole derivatives 5a and 5b, decorated with trifluoromethyl group on the phenyl ring, displayed better cytotoxicity than that of cisplatin against Bel-7402 cell line.

  DOI：

  10.1007/s00044-013-0552-1