phenyl-pyrazin-2-yl-methanone pyridin-2-ylhydrazone | 58495-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: phenyl-pyrazin-2-yl-methanone pyridin-2-ylhydrazone
• CAS: 58495-37-7
• 化学式: C₁₆H₁₃N₅
• 分子量: 275.313
• InChiKey: SPJNXKWQIKAGCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.06
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-肼吡啶 、 phenyl(pyrazin-2-yl)methanone 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以71%的产率得到phenyl-pyrazin-2-yl-methanone pyridin-2-ylhydrazone
  参考文献：
  名称：

  Azinyl and Diazinyl Hydrazones Derived from Aryl N-Heteroaryl Ketones:  Synthesis and Antiproliferative Activity^,

  摘要：

  A series of N-heteroaryl hydrazones derived from aryl N-heteroaryl or bis-N-heteroaryl methanones was prepared in search for potential novel antitumor agents. The stereochemistry of these compounds was established by means of NMR spectroscopy. Antiproliferative activity was determined in a panel of human tumor cell Lines (CCRF-CEM, Burkitt's lymphoma, HeLa, ZR-75-1, HT-29, and MEXF 276L) in vitro. Generally, the new compounds were found to be more patent (IC(50) = 0.011-0.436 mu M) than the ribonucleotide reductase inhibitor hydroxyurea (IC(50) = 140 mu M) Most of the compounds exhibited the highest activity against Burkitt's lymphoma with an IC(50) Of 0.011-0.035 mu M. [(14)C]Cytidine incorporation into DNA was quantitated for selected hydrazones (Z-A, E-1, Z-3, Z-4, E-5, Z-5, E-13, E-18, Z-19, Z-24, and E-26) as a measure of the inhibition of-ribonucleotide reductase in Burkitt's lymphoma cells. The E-configurated compounds were found to inhibit [(14)C]cytidine incorporation to a greater extent (IC(50) = 0.67-5.05 mu M) than the Z-isomers (IC(50) = 7.20 to > 10 mu M). Principal component analysis of the IC(50) values obtained for inhibition of cell proliferation revealed that the cell lines tested can be grouped into three main families showing different sensitivities toward the compounds in our series [(i) CCRF-CEM, Burkitt's lymphoma, and Hela; (ii) HT-29; and (iii) MEXF 276 L].

  DOI：

  10.1021/jm970255w