6-Hydroxy-3-methyl-3H-[1,2,3]triazolo[4,5-h]quinoline-7-carboxylic acid ethyl ester | 145548-71-6

• 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: 6-Hydroxy-3-methyl-3H-[1,2,3]triazolo[4,5-h]quinoline-7-carboxylic acid ethyl ester
• CAS: 145548-71-6
• 化学式: C₁₃H₁₂N₄O₃
• 分子量: 272.263
• InChiKey: KEBLLFOOMVQGLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  6-Hydroxy-3-methyl-3H-[1,2,3]triazolo[4,5-h]quinoline-7-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 反应 4.0h， 以97%的产率得到6-Hydroxy-3-methyl-3H-[1,2,3]triazolo[4,5-h]quinoline-7-carboxylic acid
  参考文献：
  名称：

  Sanna; Carta; Paglietti, Il Farmaco, 1992, vol. 47, # 7-8, p. 1001 - 1019

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[(1-Methyl-1H-benzotriazol-4-ylamino)-methylene]-malonic acid diethyl ester 以 various solvent(s) 为溶剂， 反应 4.0h， 以12.4%的产率得到9-Ethyl-3-methyl-6-oxo-6,9-dihydro-3H-[1,2,3]triazolo[4,5-h]quinoline-7-carboxylic acid ethyl ester
  参考文献：
  名称：

  Sanna; Carta; Paglietti, Il Farmaco, 1992, vol. 47, # 7-8, p. 1001 - 1019

  摘要：

  DOI：

文献信息

• [1,2,3]Triazolo[4,5-h]quinolones. A new class of potent antitubercular agents against multidrug resistant Mycobacterium tuberculosis strains
  作者：Antonio Carta、Michele Palomba、Giuseppe Paglietti、Paola Molicotti、Bianca Paglietti、Sara Cannas、Stefania Zanetti

  DOI：10.1016/j.bmcl.2007.06.064

  日期：2007.9

  class of antiinfective agents against MDR Mycobacterium tuberculosis. In antitubercular screening against H37Rv and 11 clinically isolated strains of M. tuberculosis several derivatives (1o,3a,c,i,j,p) showed MIC(90) in the range 0.5-3.2 microg/mL. 3c showed no cytotoxicity and proved to be the most potent derivative exhibiting MIC(90)=0.5 microg/mL against all M. tuberculosis strains and infected human

  在这项初步研究中，我们报告了3-甲基-9-取代-6-氧代-6,9-二氢-3H- [1,2,3]-三唑并[4,5-h]喹诺酮-碳含氧酸的活性和它们的酯类作为抗MDR结核分枝杆菌的新型抗感染药。在针对H37Rv和11种临床分离的结核分枝杆菌的抗结核筛选中，几种衍生物（1o，3a，c，i，j，p）的MIC（90）范围在0.5-3.2 microg / mL之间。3c没有显示出细胞毒性，并且被证明是对所有结核分枝杆菌菌株和受感染的人类巨噬细胞（J774-A1）表现出MIC（90）= 0.5 microg / mL的最有效衍生物。
• Synthesis and anti-mycobacterial activities of triazoloquinolones
  作者：Antonio Carta、Michele Palomba、Irene Briguglio、Paola Corona、Sandra Piras、Daniela Jabes、Paola Guglierame、Paola Molicotti、Stefania Zanetti

  DOI：10.1016/j.ejmech.2010.11.020

  日期：2011.1

  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.