4-benzyl-5-(4-chloro-8-(trifluoromethyl)quinolin-3-yl)-4H-1,2,4-triazole-3-thiol | 1198229-68-3

• 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: 4-benzyl-5-(4-chloro-8-(trifluoromethyl)quinolin-3-yl)-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-benzyl-3-[4-chloro-8-(trifluoromethyl)quinolin-3-yl]-1H-1,2,4-triazole-5-thione
• CAS: 1198229-68-3
• 化学式: C₁₉H₁₂ClF₃N₄S
• 分子量: 420.845
• InChiKey: KYQUIKAJKMNARO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-环己基哌嗪 、 4-benzyl-5-(4-chloro-8-(trifluoromethyl)quinolin-3-yl)-4H-1,2,4-triazole-3-thiol 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以90%的产率得到4-benzyl-5-(4-(4-cyclohexylpiperazin-1-yl)-8-(trifluoromethyl)quinolin-3-yl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety

  摘要：

  A new class of quirroline derivatives containing 1,2,4-triazole moiety were synthesized from derivatives of 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide 4 through multi-step reactions. The compound 4, on treatment with substituted Isothiocyanates yielded quinoline-thiosemicarbazides 5a-c, which were conveniently cyclized to (5-mercapto-4H-triazol-3-yl)-quinolin-4-ols 6a-c in basic medium. These intermediates were then transformed to their respective chloro derivatives 7a-c by treatment with phosphorus oxychloride, which on further reaction with different biologically active rare amines yielded the target compounds 8a-g, 9a-h and 10a-h in good yield. The ultimate step, involving nucleophilic substitution reaction was achieved by microwave-induced technique, which has reduced the reaction time drastically as well as improved the yield when compared to conventional heating. The newly synthesized final compounds were evaluated for their in vitro antibacterial and antifungal activities against four strains each. Preliminary results indicated that most of the compounds demonstrated very good antimicrobial activity, comparable to the first line standard drugs. The most effective compounds have exhibited activity at MIC of 6.25 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.031
• 作为产物：
  描述：

  3-(4-benzyl-5-mercapto-4H-1,2,4-triazol-3-yl)-8-(trifluoromethyl)quinolin-4-ol 在 三氯氧磷 作用下， 反应 2.0h， 以65%的产率得到4-benzyl-5-(4-chloro-8-(trifluoromethyl)quinolin-3-yl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety

  摘要：

  A new class of quirroline derivatives containing 1,2,4-triazole moiety were synthesized from derivatives of 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide 4 through multi-step reactions. The compound 4, on treatment with substituted Isothiocyanates yielded quinoline-thiosemicarbazides 5a-c, which were conveniently cyclized to (5-mercapto-4H-triazol-3-yl)-quinolin-4-ols 6a-c in basic medium. These intermediates were then transformed to their respective chloro derivatives 7a-c by treatment with phosphorus oxychloride, which on further reaction with different biologically active rare amines yielded the target compounds 8a-g, 9a-h and 10a-h in good yield. The ultimate step, involving nucleophilic substitution reaction was achieved by microwave-induced technique, which has reduced the reaction time drastically as well as improved the yield when compared to conventional heating. The newly synthesized final compounds were evaluated for their in vitro antibacterial and antifungal activities against four strains each. Preliminary results indicated that most of the compounds demonstrated very good antimicrobial activity, comparable to the first line standard drugs. The most effective compounds have exhibited activity at MIC of 6.25 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.06.031