3-Benzylcarbamoyl-2-oxo-chroman-8-carboxylic acid benzyl ester | 791838-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-Benzylcarbamoyl-2-oxo-chroman-8-carboxylic acid benzyl ester
• CAS: 791838-05-6
• 化学式: C₂₅H₂₁NO₅
• 分子量: 415.445
• InChiKey: HXSFMOONDULKKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-Benzylcarbamoyl-2-oxo-chroman-8-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3-(N-benzylcarbamoyl)-8-carboxy-3,4-dihydro-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Benzopyranones with retro-amide side chains as (inhibitory) β-lactamase substrates

  摘要：

  3-(N-Benzylcarbamoyl)-7-carboxy-3, 4-dihydro-2H-1-benzo-pyran-2-one and its 8-carboxy analogue have been synthesized and evaluated as potential (inhibitory) substrates of beta-lactam-recognizing enzymes. These compounds are bicyclic delta-lactones with retro-amide (with respect to classical beta-lactams) side chains. They were found to be comparably effective as substrates of typical class A, C and D beta-lactamases as analogous benzopyranones bearing 'normal' amide side chains. The new 8-carboxy derivative, however, formed a much more (1000-fold) tightly-bound acyl-enzyme with a class C beta-lactamase than did its 'normal' analogue, and thus provides a structural lead to new inhibitors of this class of beta-lactamase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.067
• 作为产物：
  描述：

  在 sodium hydroxide 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~220.0 ℃ 、1.33 Pa 条件下， 生成 3-Benzylcarbamoyl-2-oxo-chroman-8-carboxylic acid benzyl ester
  参考文献：
  名称：

  Benzopyranones with retro-amide side chains as (inhibitory) β-lactamase substrates

  摘要：

  3-(N-Benzylcarbamoyl)-7-carboxy-3, 4-dihydro-2H-1-benzo-pyran-2-one and its 8-carboxy analogue have been synthesized and evaluated as potential (inhibitory) substrates of beta-lactam-recognizing enzymes. These compounds are bicyclic delta-lactones with retro-amide (with respect to classical beta-lactams) side chains. They were found to be comparably effective as substrates of typical class A, C and D beta-lactamases as analogous benzopyranones bearing 'normal' amide side chains. The new 8-carboxy derivative, however, formed a much more (1000-fold) tightly-bound acyl-enzyme with a class C beta-lactamase than did its 'normal' analogue, and thus provides a structural lead to new inhibitors of this class of beta-lactamase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.067