(E)-2-((furan-2-yl)methylene)-1-(2,7-dimethyl-1,8-naphthyridin-4-yl)hydrazine | 1439401-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (E)-2-((furan-2-yl)methylene)-1-(2,7-dimethyl-1,8-naphthyridin-4-yl)hydrazine
• 英文别名: N-[(E)-furan-2-ylmethylideneamino]-2,7-dimethyl-1,8-naphthyridin-4-amine
• CAS: 1439401-13-4
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: SJGOGFDSNOVULN-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯-2,7-二甲基-1,8-二氮杂萘 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (E)-2-((furan-2-yl)methylene)-1-(2,7-dimethyl-1,8-naphthyridin-4-yl)hydrazine
  参考文献：
  名称：

  Synthesis, molecular docking of novel 1,8-naphthyridine derivatives and their cytotoxic activity against HepG2 cell lines

  摘要：

  A series of novel 2,7-dimethyl-1,8-naphthyridine derivatives substituted with Mannich bases 2a-d, N-beta-glycosides 6a-e, 7a-e, Schiff's bases 8a-c, pyrazolone 9, and S-alkylated derivatives 10a-c have been synthesized in good yields starting from 4-hydroxy-2,7-dimethyl-1,8-naphthyridine 1 through multi-step synthesis. The newly synthesized title compounds were evaluated for their HepG2 cell growth inhibition, the results revealed that all the tested compounds process inhibitory effects on the growth of HepG2 liver cancer cells. Compound 8b showed the highest inhibition activity against HepG2 cell line (IC50 equals 3.2 mu g/mL) among all tested compounds. The results were compared to 5-Fluorouracil (5-FU) and doxorubicin as reference drugs, (IC50 5 and 3.56 mu g/mL). Furthermore, molecular docking of compounds 3b, 6a, and 8b into the binding site of topoisomerase II was carried out. The results of the binding energy scores of these compounds were compared to the docking score of Vosaroxin, a known 1,8-naphthyridine derivative which is in clinical trials as potential anticancer drug. Compound 8b docking result revealed that it is the only tested compound that intercalate with DNA segment of the topoisomerase II, similar to Vosaroxin which was used as reference drug for docking comparison.

  DOI：

  10.1007/s00044-013-0604-6

文献信息

• Synthesis, molecular docking of novel 1,8-naphthyridine derivatives and their cytotoxic activity against HepG2 cell lines
  作者：Ahmad F. Eweas、Nagy M. Khalifa、Nisreen S. Ismail、Mohamed A. Al-Omar、Abdel Mohsen M. Soliman

  DOI：10.1007/s00044-013-0604-6

  日期：2014.1

  A series of novel 2,7-dimethyl-1,8-naphthyridine derivatives substituted with Mannich bases 2a-d, N-beta-glycosides 6a-e, 7a-e, Schiff's bases 8a-c, pyrazolone 9, and S-alkylated derivatives 10a-c have been synthesized in good yields starting from 4-hydroxy-2,7-dimethyl-1,8-naphthyridine 1 through multi-step synthesis. The newly synthesized title compounds were evaluated for their HepG2 cell growth inhibition, the results revealed that all the tested compounds process inhibitory effects on the growth of HepG2 liver cancer cells. Compound 8b showed the highest inhibition activity against HepG2 cell line (IC50 equals 3.2 mu g/mL) among all tested compounds. The results were compared to 5-Fluorouracil (5-FU) and doxorubicin as reference drugs, (IC50 5 and 3.56 mu g/mL). Furthermore, molecular docking of compounds 3b, 6a, and 8b into the binding site of topoisomerase II was carried out. The results of the binding energy scores of these compounds were compared to the docking score of Vosaroxin, a known 1,8-naphthyridine derivative which is in clinical trials as potential anticancer drug. Compound 8b docking result revealed that it is the only tested compound that intercalate with DNA segment of the topoisomerase II, similar to Vosaroxin which was used as reference drug for docking comparison.