ethyl 4-hydroxy-8-methyl-1-oxo-6-phenyl-1,2-dihydro-2,7-naphthyridine-3-carboxylate | 1186325-74-5

• 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: ethyl 4-hydroxy-8-methyl-1-oxo-6-phenyl-1,2-dihydro-2,7-naphthyridine-3-carboxylate
• 英文别名: 4-Hydroxy-8-methyl-1-oxo-6-phenyl-1,7]naphthyridine-3-carboxylic acid ethyl ester；ethyl 4-hydroxy-8-methyl-1-oxo-6-phenyl-2H-2,7-naphthyridine-3-carboxylate
• CAS: 1186325-74-5
• 化学式: C₁₈H₁₆N₂O₄
• 分子量: 324.336
• InChiKey: DJXQPTMYVIACCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-8-methyl-1-oxo-6-phenyl-1,2-dihydro-2,7-naphthyridine-3-carboxylate 在 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以89%的产率得到4-hydroxy-8-methyl-1-oxo-6-phenyl-1,2-dihydro-2,7-naphthyridine-3-carboxylic acid hydrazide
  参考文献：
  名称：

  Synthesis andIn vitroAntitumor Screening of Novel 2,7-Naphthyridine-3-carboxylic Acid Derivatives

  摘要：

  New derivatives of 2,7-naphthyridine-3-carboxylic acid were synthesized. We report the hydrolysis, chlorination, alkylation, and amination of the 2,7-naphthyridine esters 1, 2. A series of Schiff's bases 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 9a, 9b, 9b', 9c, 9d, 9e were produced by treating the obtained hydrazides 6 and 7 with aromatic aldehydes. The anticancer activities of the obtained derivatives were examined. Eighteen of the 24 newly synthesized compounds were qualified by the National Cancer Institute NCI (Bethesda, MD, USA) for in vitro screening against 60 different human tumor cell lines. The most active compound 8i was evaluated against a 60-cell panel at five concentration levels and proved to be most sensitive towards central nervous system cancer (SF-539), with GI50=0.70 mu mol, total growth inhibition=5.41 mu mol, and LC50=53.7 mu mol.

  DOI：

  10.1002/jhet.1008
• 作为产物：
  描述：

  ethyl (4-methyl-1,3-dioxo-6-phenyl-1,3-dihydro-pyrrolo[3,4-c]pyridin-2-yl)acetate 在 sodium ethanolate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以64%的产率得到ethyl 4-hydroxy-8-methyl-1-oxo-6-phenyl-1,2-dihydro-2,7-naphthyridine-3-carboxylate
  参考文献：
  名称：

  Wagner; Wojcicka; Bryndalnd, Polish Journal of Chemistry, 2009, vol. 83, # 2, p. 207 - 215

  摘要：

  DOI：

文献信息

• Wójcicka, Anna; Becan, Lilianna, Acta poloniae pharmaceutica, 2015, vol. 72, # 2, p. 297 - 305
  作者：Wójcicka, Anna、Becan, Lilianna

  DOI：——

  日期：——