4-guanidino-N-(4-sulfamoyl-benzyl)-butyramide hydrochloride | 1610893-02-1

• 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: 4-guanidino-N-(4-sulfamoyl-benzyl)-butyramide hydrochloride
• 英文别名: 4-(diaminomethylideneamino)-N-[(4-sulfamoylphenyl)methyl]butanamide
• CAS: 1610893-02-1
• 化学式: C₁₂H₁₉N₅O₃S
• 分子量: 313.381
• InChiKey: JDPBQJNWYNEURR-UHFFFAOYSA-N

物化性质

• 密度：
  1.460±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  162
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-oxo-4-((4-sulfamoylbenzyl)amino)butan-1-aminium chloride 在 盐酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 4-guanidino-N-(4-sulfamoyl-benzyl)-butyramide hydrochloride
  参考文献：
  名称：

  Synthesis of sulfonamides with effective inhibitory action against Porphyromonas gingivalis γ-carbonic anhydrase

  摘要：

  New benzenesulfonamides incorporating GABA or N-α-acetyl-L-lysine scaffolds as well as guanidine functionalities as water solubilizing moieties were obtained, using 4-aminoethyl/methyl-benzenesulfonamide and metanilamide/sulfanilamide as zinc-binding motives. The new compounds were medium potency inhibitors of the widespread cytosolic human carbonic anhydrase (CA, EC 4.2.1.1) isoforms I and II and more effective inhibitors (KIs low nanomolar range) of the bacterial γ-CA from the oral pathogen Porphyromonas gingivalis. These sulfonamides may be useful tools for understanding the physiological role of bacterial CAs in pathogenesis of some infectious disease.

  DOI：

  10.1016/j.bmcl.2014.06.024

文献信息

• New series of sulfonamides containing amino acid moiety act as effective and selective inhibitors of tumor-associated carbonic anhydrase XII
  作者：Mariangela Ceruso、Marco Bragagni、Zeid AlOthman、Sameh M. Osman、Claudiu T. Supuran

  DOI：10.3109/14756366.2014.942659

  日期：2015.5.4

  New benzenesulfonamides incorporating water solubilizing moieties were synthesized using N-alpha-acetyl-L-lysine or gamma-aminobutyric acid as scaffolds followed by the conversion of their terminal amino group to the guanidine one. Their inhibition activity was assessed by determining their K(I)s values against the human (h) carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, II, IX and XII. Some of these compounds were medium potency inhibitors of the cytosolic (CA I, II) and transmembrane (CA IX) isoforms and highly effective, nanomolar inhibitors of the second transmembrane isoform hCA XII. Some of these sulfonamides possessing good selectivity inhibition for the tumor-associated CA XII isoform over the cytosolic and physiologically dominant isoforms CA I and II may be used as tools to develop new anticancer agents.
• Synthesis of sulfonamides with effective inhibitory action against Porphyromonas gingivalis γ-carbonic anhydrase
  作者：Mariangela Ceruso、Sonia Del Prete、Zeid AlOthman、Sameh M. Osman、Andrea Scozzafava、Clemente Capasso、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2014.06.024

  日期：2014.8

  New benzenesulfonamides incorporating GABA or N-α-acetyl-L-lysine scaffolds as well as guanidine functionalities as water solubilizing moieties were obtained, using 4-aminoethyl/methyl-benzenesulfonamide and metanilamide/sulfanilamide as zinc-binding motives. The new compounds were medium potency inhibitors of the widespread cytosolic human carbonic anhydrase (CA, EC 4.2.1.1) isoforms I and II and more effective inhibitors (KIs low nanomolar range) of the bacterial γ-CA from the oral pathogen Porphyromonas gingivalis. These sulfonamides may be useful tools for understanding the physiological role of bacterial CAs in pathogenesis of some infectious disease.