2-(2,4-difluorophenyl)-1-(4-(thiophen-2-ylmethyl)piperazin-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol | 1354972-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2,4-difluorophenyl)-1-(4-(thiophen-2-ylmethyl)piperazin-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol
• 英文别名: 2-(2,4-Difluorophenyl)-1-[4-(thiophen-2-ylmethyl)piperazin-1-yl]-3-(1,2,4-triazol-1-yl)propan-2-ol
• CAS: 1354972-22-7
• 化学式: C₂₀H₂₃F₂N₅OS
• 分子量: 419.498
• InChiKey: NAYFUAKMCWQCGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-氯甲基噻吩 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 13.0h， 生成 2-(2,4-difluorophenyl)-1-(4-(thiophen-2-ylmethyl)piperazin-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol
  参考文献：
  名称：

  Discovery of highly potent triazole antifungal derivatives by heterocycle-benzene bioisosteric replacement

  摘要：

  On the basis of our previously discovered triazole antifungal lead compounds, heterocycle-benzene bioisosteric replacement was used to improve their pharmacokinetic profile. The designed new triazole derivatives have good antifungal activity toward a wide range of pathogenic fungi. Their binding mode with the target enzyme was clarified by molecular docking. The MIC value of the highly potent compound 8f against Candida albicans, Candida tropicalis, and Gyptococcus neoformans is 0.016 mu g/mL, 0.004 mu g/mL, and 0.016 mu g/mL, respectively. Moreover, preliminary pharmacokinetic studies revealed that it showed improved oral absorption as compared to the lead compound iodiconazole and deserved for further evaluations. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.025

文献信息

• Discovery of highly potent triazole antifungal derivatives by heterocycle-benzene bioisosteric replacement
  作者：Zhigan Jiang、Yan Wang、Wenya Wang、Shengzheng Wang、Bo Xu、Guorong Fan、Guoqiang Dong、Yang Liu、Jianzhong Yao、Zhenyuan Miao、Wannian Zhang、Chunquan Sheng

  DOI：10.1016/j.ejmech.2013.04.025

  日期：2013.6

  On the basis of our previously discovered triazole antifungal lead compounds, heterocycle-benzene bioisosteric replacement was used to improve their pharmacokinetic profile. The designed new triazole derivatives have good antifungal activity toward a wide range of pathogenic fungi. Their binding mode with the target enzyme was clarified by molecular docking. The MIC value of the highly potent compound 8f against Candida albicans, Candida tropicalis, and Gyptococcus neoformans is 0.016 mu g/mL, 0.004 mu g/mL, and 0.016 mu g/mL, respectively. Moreover, preliminary pharmacokinetic studies revealed that it showed improved oral absorption as compared to the lead compound iodiconazole and deserved for further evaluations. (C) 2013 Elsevier Masson SAS. All rights reserved.