4-[(3-溴-4-羟基苯基)甲基]-2-(三氟甲基)-1,3-恶唑-5-醇 | 390424-24-5

• 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-[(3-溴-4-羟基苯基)甲基]-2-(三氟甲基)-1,3-恶唑-5-醇
• 英文名称: 5-Oxazolol, 4-[(3-bromo-4-hydroxyphenyl)methyl]-2-(trifluoromethyl)-
• 英文别名: 4-[(3-bromo-4-hydroxyphenyl)methyl]-2-(trifluoromethyl)-1,3-oxazol-5-ol
• CAS: 390424-24-5
• 化学式: C₁₁H₇BrF₃NO₃
• 分子量: 338.081
• InChiKey: OQKZVUVEAGPUMG-UHFFFAOYSA-N

物化性质

• 沸点：
  354.8±42.0 °C(Predicted)
• 密度：
  1.766±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[(3-溴-4-羟基苯基)甲基]-2-(三氟甲基)-1,3-恶唑-5-醇 在 盐酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 52.0h， 生成 帕马普林A
  参考文献：
  名称：

  Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)

  摘要：

  Psammaplin A is a symmetrical bromotyrosine -derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA), Among the most active leads derived from these studies are compounds 104. 105, 113, 115, 123, and 128. The present, catalytically-induced. disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.

  DOI：

  10.1002/1521-3765(20011001)7:19<4280::aid-chem4280>3.0.co;2-3
• 作为产物：
  描述：

  3-溴-L-酪氨酸 、 三氟乙酸酐 反应 12.0h， 生成 4-[(3-溴-4-羟基苯基)甲基]-2-(三氟甲基)-1,3-恶唑-5-醇
  参考文献：
  名称：

  Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)

  摘要：

  Psammaplin A is a symmetrical bromotyrosine -derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA), Among the most active leads derived from these studies are compounds 104. 105, 113, 115, 123, and 128. The present, catalytically-induced. disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.

  DOI：

  10.1002/1521-3765(20011001)7:19<4280::aid-chem4280>3.0.co;2-3