2-(2,4-Difluoro-phenyl)-3-(2-hydroxy-ethylsulfanyl)-3-methyl-1-[1,2,4]triazol-1-yl-butan-2-ol | 167214-29-1

• 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: 2-(2,4-Difluoro-phenyl)-3-(2-hydroxy-ethylsulfanyl)-3-methyl-1-[1,2,4]triazol-1-yl-butan-2-ol
• 英文别名: 2-(2,4-Difluorophenyl)-3-(2-hydroxyethylsulfanyl)-3-methyl-1-(1,2,4-triazol-1-yl)butan-2-ol
• CAS: 167214-29-1
• 化学式: C₁₅H₁₉F₂N₃O₂S
• 分子量: 343.398
• InChiKey: RBXGQAGBQLYGSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2,4-Difluoro-phenyl)-3-(2-hydroxy-ethylsulfanyl)-3-methyl-1-[1,2,4]triazol-1-yl-butan-2-ol 在 sodium tungstate 、 双氧水 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-[(2R,5R)-2-(2,4-Difluoro-phenyl)-3,3,5-trimethyl-4,4-dioxo-4λ⁶-[1,4]oxathian-2-ylmethyl]-1H-[1,2,4]triazole
  参考文献：
  名称：

  Synthesis and antifungal activity of new azole derivatives containing an oxathiane ring

  摘要：

  A series of azole derivatives containing an oxathiane ring, which were designed to simulate the D ring of lanosterol, were synthesized and evaluated for their antifungal activity. 3,3-Dimethyl derivatives showed potent activity against murine systemic candidosis and aspergillosis, whereas (2R*,3R*)-3-monomethyl derivatives showed only weak activity in both in vitro and in vivo. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00435-0
• 作为产物：
  描述：

  2-bromo-1-(2,4-difluorophenyl)-2-methylpropan-1-one 在 甲醇 、 sodium hydroxide 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 69.5h， 生成 2-(2,4-Difluoro-phenyl)-3-(2-hydroxy-ethylsulfanyl)-3-methyl-1-[1,2,4]triazol-1-yl-butan-2-ol
  参考文献：
  名称：

  Structure-Activity Relationships of 3-Methyl and 3,3-Dimethyl Analogs of 2-(2,4-Difluorophenyl)-3-(.OMEGA.)-substituted alkyl)sulfonyl-1-(1H-1,2,4-triazol-1-yl)-2-propanols.

  摘要：

  2-(2, 4-二氟苯基)-3-(ω-取代的烷基)磺酰基-1-(1H-1, 2, 4-三唑-1-基)-2的3-甲基和3, 3-二甲基类似物合成了β-丙醇并评估了它们对白色念珠菌和烟曲霉的抗真菌活性。发现3, 3-二甲基类似物在体外和体内均比相应的3-单甲基类似物具有更有效的活性。通过3-位的二甲基化显着提高了先导化合物对鼠系统性念珠菌病和曲霉病的预防功效。

  DOI：

  10.1248/cpb.44.785

文献信息

• Structure-Activity Relationships of 3-Methyl and 3,3-Dimethyl Analogs of 2-(2,4-Difluorophenyl)-3-(.OMEGA.)-substituted alkyl)sulfonyl-1-(1H-1,2,4-triazol-1-yl)-2-propanols.
  作者：Hiroshi MIYAUCHI、Koichi KOZUKI、Tomoharu TANIO、Naohito OHASHI

  DOI：10.1248/cpb.44.785

  日期：——

  3-Methyl and 3, 3-dimethyl analogs of 2-(2, 4-difluorophenyl)-3-(ω-substituted alkyl)sulfonyl-1-(1H-1, 2, 4-triazol-1-yl)-2-propanols were synthesized and evaluated for their antifungal activites against Candida aldicans and Aspergillus fummigatus. The 3, 3-dimethyl analogs were found to have more potent activity both in vitro and in vivo than the corresponding 3-mono-methyl analogs. The prophylactic efficacy of the lead compounds against murine systemic candidiasis and aspergillosis was improved signifcantly by dimethylation of the 3-position.

  2-(2, 4-二氟苯基)-3-(ω-取代的烷基)磺酰基-1-(1H-1, 2, 4-三唑-1-基)-2的3-甲基和3, 3-二甲基类似物合成了β-丙醇并评估了它们对白色念珠菌和烟曲霉的抗真菌活性。发现3, 3-二甲基类似物在体外和体内均比相应的3-单甲基类似物具有更有效的活性。通过3-位的二甲基化显着提高了先导化合物对鼠系统性念珠菌病和曲霉病的预防功效。
• Synthesis and antifungal activity of new azole derivatives containing an oxathiane ring
  作者：Hiroshi Miyauchi、Tomoharu Tanio、Naohito Ohashi

  DOI：10.1016/0960-894x(96)00435-0

  日期：1996.10

  A series of azole derivatives containing an oxathiane ring, which were designed to simulate the D ring of lanosterol, were synthesized and evaluated for their antifungal activity. 3,3-Dimethyl derivatives showed potent activity against murine systemic candidosis and aspergillosis, whereas (2R*,3R*)-3-monomethyl derivatives showed only weak activity in both in vitro and in vivo. Copyright (C) 1996 Elsevier Science Ltd.