ethyl 3-benzyl-6-oxo-6,9-dihydro-triazolo[4,5-h]quinoline-7-carboxylate | 1055325-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 3-benzyl-6-oxo-6,9-dihydro-triazolo[4,5-h]quinoline-7-carboxylate
• CAS: 1055325-94-4
• 化学式: C₁₉H₁₆N₄O₃
• 分子量: 348.361
• InChiKey: KBDLSNNGAXTASE-UHFFFAOYSA-N

物化性质

• 熔点：
  255-257 °C(Solvent: Ethanol)
• 沸点：
  576.7±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  89.87
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  溴甲烷 、 ethyl 3-benzyl-6-oxo-6,9-dihydro-triazolo[4,5-h]quinoline-7-carboxylate 在 potassium hydroxide 、 盐酸 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 1.25h， 以34%的产率得到3-benzyl-9-methyl-6-oxo-6,9-dihydro-triazolo[4,5-h]quinoline-7-carboxylic acid
  参考文献：
  名称：

  Synthesis and anti-mycobacterial activities of triazoloquinolones

  摘要：

  A number of quinolone derivatives have been reported to possess anti-mycobacterial activity. Generally. Mycobacterium tuberculosis isolates expressing resistance to both isoniazid and rifampin are susceptible to fluoroquinolones. Benzotriazole is a hetero-bicyclic aromatic ring endowed with interesting chemical and biological properties and pharmacological activities. In a preliminary study we have recently reported the activity of triazolo[4,5-h]quinolone-carboxylic acids, a new class of benzotriazole derivatives active against multi-drug resistant M. tuberculosis (MDR-Mtb). In this study we confirm that this novel class of quinolones is endowed with a selective anti-mycobacterial activity, coupled with absence of cytotoxicity.The SAR analysis of the new derivatives in comparison with the previous series shows that the methyl group is the most effective substituent in both N-3 and N-9 positions of the ring system. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.020
• 作为产物：
  描述：

  diethyl 2-((1-benzyl-benzotriazol-4-ylamino)methylene)malonate 以 diphenyl ether-biphenyl eutectic 为溶剂， 反应 0.25h， 以55%的产率得到ethyl 3-benzyl-6-oxo-6,9-dihydro-triazolo[4,5-h]quinoline-7-carboxylate
  参考文献：
  名称：

  Synthesis and anti-mycobacterial activities of triazoloquinolones

  摘要：

  A number of quinolone derivatives have been reported to possess anti-mycobacterial activity. Generally. Mycobacterium tuberculosis isolates expressing resistance to both isoniazid and rifampin are susceptible to fluoroquinolones. Benzotriazole is a hetero-bicyclic aromatic ring endowed with interesting chemical and biological properties and pharmacological activities. In a preliminary study we have recently reported the activity of triazolo[4,5-h]quinolone-carboxylic acids, a new class of benzotriazole derivatives active against multi-drug resistant M. tuberculosis (MDR-Mtb). In this study we confirm that this novel class of quinolones is endowed with a selective anti-mycobacterial activity, coupled with absence of cytotoxicity.The SAR analysis of the new derivatives in comparison with the previous series shows that the methyl group is the most effective substituent in both N-3 and N-9 positions of the ring system. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.020