(2R-cis)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran | 310882-09-8

• 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: (2R-cis)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran
• CAS: 310882-09-8
• 化学式: C₁₅H₁₄F₂N₄O
• 分子量: 304.299
• InChiKey: BGTBMXRRTOHZMC-NHYWBVRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.73
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R-cis)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 1,8-diazabicyclo[5.4.0]-undecen-7-ene 、 盐酸羟胺 、 氢气 、 二异丁基氢化铝 、 lithium chloride 、 nickel dichloride 作用下， 以 甲醇 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 9.0h， 生成 (2R-cis)-4-(4-amino-5-methylhexyl)-2-(2,4-difluorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran
  参考文献：
  名称：

  Design and synthesis of potential inhibitors of the ergosterol biosynthesis as antifungal agents

  摘要：

  A series of azolylmethyloxolane derivatives with modified sterol side-chain structures, designed as potential dual functional inhibitors of cytochrome P450 14 alpha-demethylase (14DM) and Delta(24)-sterol methyltransferase (24-SMT) based on the common characteristic features of 24-aminosterols and azole antifungal agents, were synthesized and evaluated for their antifungal activities and inhibitory activities of 14DM and 24-SMT. Among these compounds, imidazolylmethyloxolane derivatives 28a and 28b showed potent in vitro antifungal activities comparable to those of itraconazole. However, the in vitro bioactivities have not been linearly translated into in vivo protection data for some unknown reasons. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00177-2
• 作为产物：
  描述：

  氰化钾 、 (5R-CIS)-甲苯-4-磺酸 5-(2,4-二氟苯基)-5-(1H-1,2,4-三氮唑-1-基)甲基四氢呋喃-3-基甲基酯 以 二甲基亚砜 为溶剂， 反应 15.0h， 以84.5%的产率得到(2R-cis)-4-cyanomethyl-2-(2,4-difluorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran
  参考文献：
  名称：

  Design and synthesis of potential inhibitors of the ergosterol biosynthesis as antifungal agents

  摘要：

  A series of azolylmethyloxolane derivatives with modified sterol side-chain structures, designed as potential dual functional inhibitors of cytochrome P450 14 alpha-demethylase (14DM) and Delta(24)-sterol methyltransferase (24-SMT) based on the common characteristic features of 24-aminosterols and azole antifungal agents, were synthesized and evaluated for their antifungal activities and inhibitory activities of 14DM and 24-SMT. Among these compounds, imidazolylmethyloxolane derivatives 28a and 28b showed potent in vitro antifungal activities comparable to those of itraconazole. However, the in vitro bioactivities have not been linearly translated into in vivo protection data for some unknown reasons. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00177-2