{Ethoxycarbonylmethyl-[4-(2-{2-[2-(4-sulfamoyl-benzoylamino)-ethoxy]-ethoxy}-ethylcarbamoyl)-benzyl]-amino}-acetic acid ethyl ester | 796113-65-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {Ethoxycarbonylmethyl-[4-(2-{2-[2-(4-sulfamoyl-benzoylamino)-ethoxy]-ethoxy}-ethylcarbamoyl)-benzyl]-amino}-acetic acid ethyl ester
• CAS: 796113-65-0
• 化学式: C₂₉H₄₀N₄O₁₀S
• 分子量: 636.723
• InChiKey: GWTOFHYOGOQINP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  44.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  192.66
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  {Ethoxycarbonylmethyl-[4-(2-{2-[2-(4-sulfamoyl-benzoylamino)-ethoxy]-ethoxy}-ethylcarbamoyl)-benzyl]-amino}-acetic acid ethyl ester 在 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以63%的产率得到2-[Carboxymethyl-[[4-[2-[2-[2-[(4-sulfamoylbenzoyl)amino]ethoxy]ethoxy]ethylcarbamoyl]phenyl]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：

  亚氨基二乙酸二乙酯 在 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 27.0h， 生成 {Ethoxycarbonylmethyl-[4-(2-{2-[2-(4-sulfamoyl-benzoylamino)-ethoxy]-ethoxy}-ethylcarbamoyl)-benzyl]-amino}-acetic acid ethyl ester
  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