4-(2-氟苯基)-1H-1,2,4-噻唑-5(4H)-酮 | 1065074-15-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(2-氟苯基)-1H-1,2,4-噻唑-5(4H)-酮
• 中文别名: 4-(2-氟苯基)-1H-1,2,4-三唑-5(4H)-酮
• 英文名称: 4-(2-Fluorophenyl)-1H-1,2,4-triazol-5(4H)-one
• 英文别名: 4-(2-fluorophenyl)-1H-1,2,4-triazol-5-one
• CAS: 1065074-15-8
• 化学式: C₈H₆FN₃O
• mdl: MFCD11504880
• 分子量: 179.154
• InChiKey: RUAZYMIYEVXDRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-氟苯基)-1H-1,2,4-噻唑-5(4H)-酮 在 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 1-(3-(4-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl) piperazin-1-yl)propyl)-4-(2-fluorophenyl)-1H-1,2,4-triazol-5(4H)-one
  参考文献：
  名称：

  Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism

  摘要：

  The incidence of life-threatening fungal infections is increasing dramatically. In an attempt to develop novel antifungal agents, our previously synthesized phenoxyalkylpiperazine triazole derivatives were used as lead structures for further optimization. By means of structure-based bioisosterism, triazolone was used as a new bioisostere of oxygen atom. This type of bioisosteric replacement can improve the water solubility without loss of hydrogen-bonding interaction with the target enzyme. A series of triazolone-containing triazoles were rationally designed and synthesized. As compared with fluconazole, several compounds showed higher antifungal activity with broader spectrum, suggesting their potential for further evaluations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.019
• 作为产物：
  描述：

  4-(2-fluoro-phenyl)semicarbazide 、 醋酸甲脒 在 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4-(2-氟苯基)-1H-1,2,4-噻唑-5(4H)-酮
  参考文献：
  名称：

  Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism

  摘要：

  The incidence of life-threatening fungal infections is increasing dramatically. In an attempt to develop novel antifungal agents, our previously synthesized phenoxyalkylpiperazine triazole derivatives were used as lead structures for further optimization. By means of structure-based bioisosterism, triazolone was used as a new bioisostere of oxygen atom. This type of bioisosteric replacement can improve the water solubility without loss of hydrogen-bonding interaction with the target enzyme. A series of triazolone-containing triazoles were rationally designed and synthesized. As compared with fluconazole, several compounds showed higher antifungal activity with broader spectrum, suggesting their potential for further evaluations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.019

文献信息

• Design and synthesis of novel triazole antifungal derivatives by structure-based bioisosterism
  作者：Chunquan Sheng、Xiaoying Che、Wenya Wang、Shengzheng Wang、Yongbing Cao、Zhenyuan Miao、Jianzhong Yao、Wannian Zhang

  DOI：10.1016/j.ejmech.2011.03.019

  日期：2011.11

  The incidence of life-threatening fungal infections is increasing dramatically. In an attempt to develop novel antifungal agents, our previously synthesized phenoxyalkylpiperazine triazole derivatives were used as lead structures for further optimization. By means of structure-based bioisosterism, triazolone was used as a new bioisostere of oxygen atom. This type of bioisosteric replacement can improve the water solubility without loss of hydrogen-bonding interaction with the target enzyme. A series of triazolone-containing triazoles were rationally designed and synthesized. As compared with fluconazole, several compounds showed higher antifungal activity with broader spectrum, suggesting their potential for further evaluations. (C) 2011 Elsevier Masson SAS. All rights reserved.