3-(N-benzylcarbamoyl)-7-carboxy-3,4-dihydro-2H-1-benzopyran-2-one | 791838-08-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 3-(N-benzylcarbamoyl)-7-carboxy-3,4-dihydro-2H-1-benzopyran-2-one
• 英文别名: 3-(Benzylcarbamoyl)-2-oxo-3,4-dihydrochromene-7-carboxylic acid
• CAS: 791838-08-9
• 化学式: C₁₈H₁₅NO₅
• 分子量: 325.321
• InChiKey: QGIDDXJDDCRFQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(N-benzylcarbamoyl)-7-carboxy-3,4-dihydro-2H-1-benzopyran-2-one 在 Enterobacter cloacae P99 β-lactamase class C 、 水 作用下， 生成 4-(2-Benzylcarbamoyl-2-carboxy-ethyl)-3-hydroxy-benzoic acid
  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：

  3-(苄基氨基)-3-氧代丙酸甲酯 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium hydride 、 caesium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0~220.0 ℃ 、1.33 Pa 条件下， 生成 3-(N-benzylcarbamoyl)-7-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

文献信息

• Benzopyranones with retro-amide side chains as (inhibitory) β-lactamase substrates
  作者：S.A. Adediran、D. Cabaret、J.-F. Lohier、M. Wakselman、R.F. Pratt

  DOI：10.1016/j.bmcl.2004.07.067

  日期：2004.10

  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.