1-({[5-(tert-butoxycarbonyl)-1,3-dioxolo[4,5-f ]indol-7-yl]methyl}methylamino)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol | 1292799-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-({[5-(tert-butoxycarbonyl)-1,3-dioxolo[4,5-f ]indol-7-yl]methyl}methylamino)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol
• CAS: 1292799-35-9
• 化学式: C₂₇H₂₉F₂N₅O₅
• 分子量: 541.555
• InChiKey: JUWSUDPADGLIRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  103.87
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-({[5-(tert-butoxycarbonyl)-1,3-dioxolo[4,5-f ]indol-7-yl]methyl}methylamino)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol 在 zinc dibromide 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以21%的产率得到1-{[(5H-1,3-dioxolo[4,5-f]indol-7-yl)methyl]methylamino}-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol
  参考文献：
  名称：

  Synthesis and in vitro antifungal evaluation of 2-(2,4-difluorophenyl)-1-[(1H-indol-3-ylmethyl)methylamino]-3-(1H-1,2,4-triazol-1-yl)propan-2-ols

  摘要：

  We extended our previous studies based on the design of 1-[(1H-indol-5-ylmethyl)amino]-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents toward the identification of new indol-3-ylmethylamino derivatives. The majority of these compounds exhibited antifungal activity against a Candida albicans strain (minimum inhibitory concentrations ranging from 199.0 to 381.0 ng/mL) suggesting an inhibition of 14 alpha alpha-demethylase by sterol analysis studies, but are weaker inhibitors compared to their indol-5-ylmethylamino analogs.

  DOI：

  10.3109/14756366.2010.503607
• 作为产物：
  描述：

  5H-1,3-dioxolo[4,5-f ]indole-7-carbaldehyde 在 4-二甲氨基吡啶 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 26.0h， 生成 1-({[5-(tert-butoxycarbonyl)-1,3-dioxolo[4,5-f ]indol-7-yl]methyl}methylamino)-2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol
  参考文献：
  名称：

  Synthesis and in vitro antifungal evaluation of 2-(2,4-difluorophenyl)-1-[(1H-indol-3-ylmethyl)methylamino]-3-(1H-1,2,4-triazol-1-yl)propan-2-ols

  摘要：

  We extended our previous studies based on the design of 1-[(1H-indol-5-ylmethyl)amino]-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols as antifungal agents toward the identification of new indol-3-ylmethylamino derivatives. The majority of these compounds exhibited antifungal activity against a Candida albicans strain (minimum inhibitory concentrations ranging from 199.0 to 381.0 ng/mL) suggesting an inhibition of 14 alpha alpha-demethylase by sterol analysis studies, but are weaker inhibitors compared to their indol-5-ylmethylamino analogs.

  DOI：

  10.3109/14756366.2010.503607