(S)-2-(4-acetylphenoxy)-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoic acid | 1262547-67-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-(4-acetylphenoxy)-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoic acid
• 英文别名: (2S)-2-(4-acetylphenoxy)-3-[2-[3-(5-methyl-2-phenyl-oxazol-4-yl)propyl]-1,3-benzoxazol-5-yl]propanoic acid；(2S)-2-(4-acetylphenoxy)-3-[2-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]-1,3-benzoxazol-5-yl]propanoic acid
• CAS: 1262547-67-0
• 化学式: C₃₁H₂₈N₂O₆
• 分子量: 524.573
• InChiKey: FMXLLGXKYJYKJK-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (S)-3-((S)-2-hydroxy-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoyl)-4-isopropyl oxazolidin-2-one 在 lithium hydroxide monohydrate 、 偶氮二甲酸二异丙酯 、 乙基溴化镁 、 三苯基膦 作用下， 以 乙醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 14.17h， 生成 (S)-2-(4-acetylphenoxy)-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoic acid
  参考文献：
  名称：

  Design, synthesis and antimicrobial activity of chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives

  摘要：

  Chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives were synthesized and their antibacterial activities were evaluated against fungus, Gram-negative and Gram-positive bacteria. In general, these compounds showed in vitro activities against all screened Gram-negative and Gram-positive bacteria, but poor MIC values for fungus Candida albicans. Remarkably, the (S)-configuration-substituted phenoxyl side chain on position 2 of propanoic acid exerted excellent antibacterial activity against all screened bacteria. Preliminary structure activity studies revealed that the hydrophobic substitutes, para-tert-butyl (11r), para-phenyl (11s) and para-benzyloxy (11t) on the phenoxyl side chain displayed best activities against all Gram-negative and Gram-positive bacteria with MIC values between 1.56 and 6.25 mu g/mL. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.028