(S)-4-hydroxy-6-(hydroxy(phenyl)methyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid | 1300040-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-4-hydroxy-6-(hydroxy(phenyl)methyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid
• CAS: 1300040-41-8
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: FNNUKJWJLBEVLE-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  110.62
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-4-hydroxy-6-(hydroxy(phenyl)methyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid 、 (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 以82%的产率得到4-hydroxy-2-oxo-6-((S)-phenyl((R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyloxy) methyl)-1,2-dihydropyridine-3-carboxylic acid
  参考文献：
  名称：

  SPF32629A and SPF32629B: Enantioselective synthesis, determination of absolute configuration, cytotoxicity and antibacterial evaluation

  摘要：

  We report herein an efficient enantioselective synthesis of SPF32629A and SPF32629B through one-pot enantioselective reduction and protecting-group-free regioselective O-acylation strategy. The absolute configuration of the enantiomerically pure isomers was established by Mosher ester analysis. The inhibitory potencies of the synthesized compounds were assayed in vitro against a panel of microorganisms and against A549 human lung adenocarcinoma cell line. Compounds 2, 11 and 12 displayed moderate to potent antibacterial activity against all the tested strains and compounds 7, 8, 2, 11 and 12 exhibited significant cytotoxicity in a dose-dependent manner with an IC50 values ranging from 2.92 to 4.14 mu g/ml and 8-11 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.039
• 作为产物：
  描述：

  6-benzoyl-4-hydroxy-2-oxo-1H-pyridine-3-carboxylic acid 在 (-)-diisopinocamphenylborane chloride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (S)-4-hydroxy-6-(hydroxy(phenyl)methyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid
  参考文献：
  名称：

  SPF32629A and SPF32629B: Enantioselective synthesis, determination of absolute configuration, cytotoxicity and antibacterial evaluation

  摘要：

  We report herein an efficient enantioselective synthesis of SPF32629A and SPF32629B through one-pot enantioselective reduction and protecting-group-free regioselective O-acylation strategy. The absolute configuration of the enantiomerically pure isomers was established by Mosher ester analysis. The inhibitory potencies of the synthesized compounds were assayed in vitro against a panel of microorganisms and against A549 human lung adenocarcinoma cell line. Compounds 2, 11 and 12 displayed moderate to potent antibacterial activity against all the tested strains and compounds 7, 8, 2, 11 and 12 exhibited significant cytotoxicity in a dose-dependent manner with an IC50 values ranging from 2.92 to 4.14 mu g/ml and 8-11 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.039