4-hydroxy-6-((3-methylbutanoyloxy)(phenyl)methyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid | 1228648-54-1

• 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: 4-hydroxy-6-((3-methylbutanoyloxy)(phenyl)methyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid
• 英文别名: (+/-)-SPF32629B；4-Hydroxy-6-{[(3-methylbutanoyl)oxy](phenyl)methyl}-2-oxo-1,2-dihydropyridine-3-carboxylic acid；4-hydroxy-6-[3-methylbutanoyloxy(phenyl)methyl]-2-oxo-1H-pyridine-3-carboxylic acid
• CAS: 1228648-54-1
• 化学式: C₁₈H₁₉NO₆
• 分子量: 345.352
• InChiKey: RQSUJBPFSUWQSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-benzoyl-4-hydroxy-2-oxo-1H-pyridine-3-carboxylic acid 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 4-hydroxy-6-((3-methylbutanoyloxy)(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

文献信息

• The first total synthesis of potent human chymase inhibitor SPF32629B via regioselective bromination and O-acylation strategy
  作者：Srinivasa Rao Vegi、Shanthaveerappa K. Boovanahalli、Balaram Patro、K. Mukkanti

  DOI：10.1016/j.tetlet.2010.03.091

  日期：2010.5

  An efficient total synthesis of (+/-)-SPF32629B is described. The key features of the synthesis include regioselective bromination followed by carboxylation at C-3 and protecting-group-free regioselective acylation of hydroxyl group present at C7. Structure was determined by X-ray analysis. (C) 2010 Elsevier Ltd. All rights reserved.