4-(4-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)benzylidene)-2-phenyloxazol-5(4H)-one | 1330676-45-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(4-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)benzylidene)-2-phenyloxazol-5(4H)-one
• 英文别名: 4-[[4-[2-(2,4-difluorophenyl)-2-hydroxy-3-(1,2,4-triazol-1-yl)propoxy]phenyl]methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 1330676-45-3
• 化学式: C₂₇H₂₀F₂N₄O₄
• 分子量: 502.477
• InChiKey: LTYIWNATVUANBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  98.83
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-(4-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)benzylidene)-2-phenyloxazol-5(4H)-one 在 sodium hydroxide 、 双氧水 作用下， 以 水 为溶剂， 反应 7.0h， 以33%的产率得到2-(4-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)phenyl)acetic acid
  参考文献：
  名称：

  Novel hybrids of fluconazole and furanones: Design, synthesis and antifungal activity

  摘要：

  During our efforts to develop new antifungal agents, a number of hybrid molecules containing furanones and fluconazole pharmacophores were designed and synthesized. The new chemical entities thus synthesized were tested for their potential as antifungal agents against various fungal strains and it was observed that the compounds with general structure 7 were potent inhibitors of Candida albicans ATCC 24433, Candida glabrata ATCC 90030, Candida tropicalis ATCC 750 and Candida neoformans ATCC 34664 while the fluconazole analogues 12 exhibited antifungal activity against Candida albicans ATCC 24433 and Candida glabrata ATCC 90030. The structure-activity relationship for these compounds is discussed. The synthetic strategies used in the present work have potential to prepare a large number of compounds for further refinement of structures to obtain molecules suitable for development as antifungal drugs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.022
• 作为产物：
  描述：

  对羟基苯甲醛 在 四丁基溴化铵 、 sodium acetate 、 乙酸酐 、 potassium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 14.0h， 生成 4-(4-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propoxy)benzylidene)-2-phenyloxazol-5(4H)-one
  参考文献：
  名称：

  Novel hybrids of fluconazole and furanones: Design, synthesis and antifungal activity

  摘要：

  During our efforts to develop new antifungal agents, a number of hybrid molecules containing furanones and fluconazole pharmacophores were designed and synthesized. The new chemical entities thus synthesized were tested for their potential as antifungal agents against various fungal strains and it was observed that the compounds with general structure 7 were potent inhibitors of Candida albicans ATCC 24433, Candida glabrata ATCC 90030, Candida tropicalis ATCC 750 and Candida neoformans ATCC 34664 while the fluconazole analogues 12 exhibited antifungal activity against Candida albicans ATCC 24433 and Candida glabrata ATCC 90030. The structure-activity relationship for these compounds is discussed. The synthetic strategies used in the present work have potential to prepare a large number of compounds for further refinement of structures to obtain molecules suitable for development as antifungal drugs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.022

文献信息

• Novel hybrids of fluconazole and furanones: Design, synthesis and antifungal activity
  作者：Hanumant B. Borate、Sangmeshwer P. Sawargave、Subhash P. Chavan、Mohan A. Chandavarkar、Ramki Iyer、Amit Tawte、Deepali Rao、Jaydeep V. Deore、Ananada S. Kudale、Pankaj S. Mahajan、Gopinath S. Kangire

  DOI：10.1016/j.bmcl.2011.06.022

  日期：2011.8

  During our efforts to develop new antifungal agents, a number of hybrid molecules containing furanones and fluconazole pharmacophores were designed and synthesized. The new chemical entities thus synthesized were tested for their potential as antifungal agents against various fungal strains and it was observed that the compounds with general structure 7 were potent inhibitors of Candida albicans ATCC 24433, Candida glabrata ATCC 90030, Candida tropicalis ATCC 750 and Candida neoformans ATCC 34664 while the fluconazole analogues 12 exhibited antifungal activity against Candida albicans ATCC 24433 and Candida glabrata ATCC 90030. The structure-activity relationship for these compounds is discussed. The synthetic strategies used in the present work have potential to prepare a large number of compounds for further refinement of structures to obtain molecules suitable for development as antifungal drugs. (C) 2011 Elsevier Ltd. All rights reserved.