6-amino-11-furylpyrido[3,4-c][1,9]phenanthroline | 1401971-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 6-amino-11-furylpyrido[3,4-c][1,9]phenanthroline
• 英文别名: 5-(Furan-2-yl)pyrido[3,4-c][1,9]phenanthrolin-12-amine；5-(furan-2-yl)pyrido[3,4-c][1,9]phenanthrolin-12-amine
• CAS: 1401971-82-1
• 化学式: C₁₉H₁₂N₄O
• 分子量: 312.33
• InChiKey: NIWHXIGHXQTYQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氰基-4-甲基吡啶 在 palladium 10% on activated carbon 、 potassium tert-butylate 作用下， 反应 2.25h， 生成 6-amino-11-furylpyrido[3,4-c][1,9]phenanthroline
  参考文献：
  名称：

  Synthesis and physicochemical characterization of novel 6-aminopyrido[3,4-c][1,9]phenanthrolines as aza-analogs of benzo[c]phenanthridines

  摘要：

  Based on the 6-aminobenzo[c]phenanthridines, a compound class showing noteworthy antitumor activity, an efficient one-step synthesis consisting of a base-catalyzed condensation of 2 equiv of 4-methylpyridine-3-carbonitrile and various aldehydes causing twofold ring closure is described. The obtained 6-amino-11,12-dihydropyrido[3,4-c][1,9]phenanthrolines could be aromatized with Pd/C at high temperatures to form 6-aminopyrido[3,4-c][1,9]phenanthrolines. All compounds were systematically characterized regarding both lipophilicity and solubility and a high cytotoxic potential was evaluated in preliminary in vitro studies. Compared to formerly described 6-aminobenzo[c]phenanthridines our newly developed phenanthrolines turned out to possess improved drugability, due to significantly increased water-solubility and decreased lipophilicity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.047

文献信息

• Synthesis and physicochemical characterization of novel 6-aminopyrido[3,4-c][1,9]phenanthrolines as aza-analogs of benzo[c]phenanthridines
  作者：Christopher Meier、Joscha Kotthaus、Lars Stenzel、Ulrich Girreser、Dieter Heber、Bernd Clement

  DOI：10.1016/j.tet.2012.08.047

  日期：2012.11

  Based on the 6-aminobenzo[c]phenanthridines, a compound class showing noteworthy antitumor activity, an efficient one-step synthesis consisting of a base-catalyzed condensation of 2 equiv of 4-methylpyridine-3-carbonitrile and various aldehydes causing twofold ring closure is described. The obtained 6-amino-11,12-dihydropyrido[3,4-c][1,9]phenanthrolines could be aromatized with Pd/C at high temperatures to form 6-aminopyrido[3,4-c][1,9]phenanthrolines. All compounds were systematically characterized regarding both lipophilicity and solubility and a high cytotoxic potential was evaluated in preliminary in vitro studies. Compared to formerly described 6-aminobenzo[c]phenanthridines our newly developed phenanthrolines turned out to possess improved drugability, due to significantly increased water-solubility and decreased lipophilicity. (C) 2012 Elsevier Ltd. All rights reserved.