2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl 4-(4-fluorophenyl)piperazine-1-carbodithioate | 1453219-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl 4-(4-fluorophenyl)piperazine-1-carbodithioate
• 英文别名: [2-(2,4-Difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl] 4-(4-fluorophenyl)piperazine-1-carbodithioate；[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl] 4-(4-fluorophenyl)piperazine-1-carbodithioate
• CAS: 1453219-10-7
• 化学式: C₂₂H₂₂F₃N₅OS₂
• 分子量: 493.577
• InChiKey: QEMXXQNAWSRNAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氯-2',4'-二氟苯乙酮 在 碳酸氢钠 、 cetyl trimethyl ammonium bromide 、 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 13.0h， 生成 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl 4-(4-fluorophenyl)piperazine-1-carbodithioate
  参考文献：
  名称：

  Synthesis, antifungal activities and molecular docking studies of novel 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl dithiocarbamates

  摘要：

  A series of 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl dithiocarbamates as new analogs of fluconazole were synthesized and their antifungal activities were evaluated. Among these compounds, 2a-f and 3a-q exhibited higher activities than fluconazole against nearly all fungi tested except Aspergillus fumigatus. Noticeably, the in vitro biological activities of 2b, 3a, 3c, 3h-k, and 3o-q against Candida species were much better than those of fluconazole and ketoconazole. Also, 2a-d, 3a-d, 3e-f, 3h-k, 3p and 3q showed higher activities against A. fumi than fluconazole. Computational docking experiments indicated that the inhibition of CYP51 involved a coordination bond with iron of the heme group, the hydrophilic H-bonding region, the hydrophobic region, and the narrow hydrophobic cleft. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.009

文献信息

• Synthesis, antifungal activities and molecular docking studies of novel 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl dithiocarbamates
  作者：Yan Zou、Shichong Yu、Renwu Li、Qingjie Zhao、Xiang Li、Maocheng Wu、Ting Huang、Xiaoxun Chai、Honggang Hu、Qiuye Wu

  DOI：10.1016/j.ejmech.2014.01.009

  日期：2014.3

  A series of 2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl dithiocarbamates as new analogs of fluconazole were synthesized and their antifungal activities were evaluated. Among these compounds, 2a-f and 3a-q exhibited higher activities than fluconazole against nearly all fungi tested except Aspergillus fumigatus. Noticeably, the in vitro biological activities of 2b, 3a, 3c, 3h-k, and 3o-q against Candida species were much better than those of fluconazole and ketoconazole. Also, 2a-d, 3a-d, 3e-f, 3h-k, 3p and 3q showed higher activities against A. fumi than fluconazole. Computational docking experiments indicated that the inhibition of CYP51 involved a coordination bond with iron of the heme group, the hydrophilic H-bonding region, the hydrophobic region, and the narrow hydrophobic cleft. (C) 2014 Elsevier Masson SAS. All rights reserved.