4-[2-(Bis-ethoxycarbonylmethyl-amino)-acetylamino]-benzoic acid | 796113-60-5

• 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-[2-(Bis-ethoxycarbonylmethyl-amino)-acetylamino]-benzoic acid
• CAS: 796113-60-5
• 化学式: C₁₇H₂₂N₂O₇
• 分子量: 366.371
• InChiKey: HYWILKFMTHDSEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  574.2±50.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.75
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  122.24
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-[2-(Bis-ethoxycarbonylmethyl-amino)-acetylamino]-benzoic acid 在 lithium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 生成 (Carboxymethyl-{[4-(2-{2-[2-(4-sulfamoyl-benzoylamino)-ethoxy]-ethoxy}-ethylcarbamoyl)-phenylcarbamoyl]-methyl}-amino)-acetic acid
  参考文献：
  名称：

  Two-Prong Inhibitors for Human Carbonic Anhydrase II

  摘要：

  The enzyme inhibitors are usually designed by taking into consideration the overall dimensions of the enzyme's active site pockets. This conventional approach often fails to produce desirable affinities of inhibitors for their cognate enzymes. To circumvent such constraints, we contemplated enhancing the binding affinities of inhibitors by attaching tether groups, which would interact with the surface exposed amino acid residues. This strategy has been tested for the inhibition of human carbonic anhydrase II. Benzenesulfonamide serves as a weak inhibitor for the enzyme, but when it is conjugated to iminodiacetate-Cu2+ (which interacts with the surface-exposed His residues) via a spacer group, its binding affinity is enhanced by about 2 orders of magnitude. This "two-prong" approach is expected to serve as a general strategy for converting weak inhibitors of enzymes into tight-binding inhibitors.

  DOI：

  10.1021/ja047271k
• 作为产物：
  描述：

  对氨基苯甲酸 、 2-(bis(2-ethoxy-2-oxoethyl)amino)acetic acid 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 乙酸乙酯 、 氯仿 为溶剂， 反应 8.75h， 以64%的产率得到4-[2-(Bis-ethoxycarbonylmethyl-amino)-acetylamino]-benzoic acid
  参考文献：
  名称：

  Two-Prong Inhibitors for Human Carbonic Anhydrase II

  摘要：

  The enzyme inhibitors are usually designed by taking into consideration the overall dimensions of the enzyme's active site pockets. This conventional approach often fails to produce desirable affinities of inhibitors for their cognate enzymes. To circumvent such constraints, we contemplated enhancing the binding affinities of inhibitors by attaching tether groups, which would interact with the surface exposed amino acid residues. This strategy has been tested for the inhibition of human carbonic anhydrase II. Benzenesulfonamide serves as a weak inhibitor for the enzyme, but when it is conjugated to iminodiacetate-Cu2+ (which interacts with the surface-exposed His residues) via a spacer group, its binding affinity is enhanced by about 2 orders of magnitude. This "two-prong" approach is expected to serve as a general strategy for converting weak inhibitors of enzymes into tight-binding inhibitors.

  DOI：

  10.1021/ja047271k