2-(2,4-difluorophenyl)-1-(6-fluoro-1H-benzo[d][1,2,3]-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol | 1228885-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 2-(2,4-difluorophenyl)-1-(6-fluoro-1H-benzo[d][1,2,3]-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol
• 英文别名: 2-(2,4-Difluorophenyl)-1-(6-fluorobenzotriazol-1-yl)-3-(1,2,4-triazol-1-yl)propan-2-ol
• CAS: 1228885-19-5
• 化学式: C₁₇H₁₃F₃N₆O
• 分子量: 374.325
• InChiKey: VTMCRSGRBIWXOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-[2-(2,4-二氟苯基)-2,3-环氧基丙基]-1H-1,2,4-噻唑 、 5-氟-1H-苯并三唑 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以35.7%的产率得到2-(2,4-difluorophenyl)-1-(5-fluoro-1H-benzo[d][1,2,3]-triazol-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol
  参考文献：
  名称：

  Design, synthesis and determination of antifungal activity of 5(6)-substituted benzotriazoles

  摘要：

  In an effort to find inhibitors that are effective against both Candida and Aspergillus spp., a series of 5(6)-(un)substituted benzotriazole analogs, represented by compounds 3a-3h and 3b'-3f', were prepared using a crystalline oxirane intermediate 1 previously synthesized in our laboratory. All the compounds were evaluated for inhibitory activity against various species of Candida and Aspergillus Compounds 3b' (5,6-dimethylbenzotriazol-2-yl derivative), 3d (5-chlorobenzotriazol-1-yl derivative) and 3e' (6-methylbenzotriazol-1-yl derivative) exhibited potent antifungal activity, with the MICs for Candida spp. and Aspergillus niger, ranging from 1 6 mu g/mL to 25 mu g/mL and 125 mu g/mL to 25 mu g/mL, respectively. The present work describes the design, synthesis, regioisomer characterization (through COSY and NOESY 2D-NMR spectroscopy and single molecule X-ray crystallography), antifungal evaluation, molecular docking, and structure-activity relationships of the various 5(6)-(un)substituted benzotriazole analogs.

  DOI：

  10.1016/j.ejmech.2010.01.062

文献信息

• Design, synthesis and determination of antifungal activity of 5(6)-substituted benzotriazoles
  作者：Pallav D. Patel、Maulik R. Patel、Bela Kocsis、Erika Kocsis、Steven M. Graham、Andrew R. Warren、Stacia M. Nicholson、Blase Billack、Frank R. Fronczek、Tanaji T. Talele

  DOI：10.1016/j.ejmech.2010.01.062

  日期：2010.6

  In an effort to find inhibitors that are effective against both Candida and Aspergillus spp., a series of 5(6)-(un)substituted benzotriazole analogs, represented by compounds 3a-3h and 3b'-3f', were prepared using a crystalline oxirane intermediate 1 previously synthesized in our laboratory. All the compounds were evaluated for inhibitory activity against various species of Candida and Aspergillus Compounds 3b' (5,6-dimethylbenzotriazol-2-yl derivative), 3d (5-chlorobenzotriazol-1-yl derivative) and 3e' (6-methylbenzotriazol-1-yl derivative) exhibited potent antifungal activity, with the MICs for Candida spp. and Aspergillus niger, ranging from 1 6 mu g/mL to 25 mu g/mL and 125 mu g/mL to 25 mu g/mL, respectively. The present work describes the design, synthesis, regioisomer characterization (through COSY and NOESY 2D-NMR spectroscopy and single molecule X-ray crystallography), antifungal evaluation, molecular docking, and structure-activity relationships of the various 5(6)-(un)substituted benzotriazole analogs.