N-acetylamino-N'-di-(tert-butyloxycarbonyl)guanidinohexanoic acid [2-(4-sulfamoylphenyl)ethyl]amide | 1610892-95-9

• 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: N-acetylamino-N'-di-(tert-butyloxycarbonyl)guanidinohexanoic acid [2-(4-sulfamoylphenyl)ethyl]amide
• 英文别名: N-acetylamino-N'-diBoc-guanidinohexanoic acid [2-(4-sulfamoylphenyl)ethyl]amide
• CAS: 1610892-95-9
• 化学式: C₂₇H₄₄N₆O₈S
• 分子量: 612.748
• InChiKey: RSDQBPBIBVJSTA-NRFANRHFSA-N

物化性质

• 密度：
  1.263±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  207.38
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-acetylamino-N'-di-(tert-butyloxycarbonyl)guanidinohexanoic acid [2-(4-sulfamoylphenyl)ethyl]amide 在 盐酸 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  New series of sulfonamides containing amino acid moiety act as effective and selective inhibitors of tumor-associated carbonic anhydrase XII

  摘要：

  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.

  DOI：

  10.3109/14756366.2014.942659
• 作为产物：
  描述：

  5-acetylamino-5-[2-(4-sulfamoylphenyl)ethylcarbamoyl]pentylammonium chloride 、 1,3-二-BOC-2-(三氟甲基磺酰)胍 在 三乙胺 作用下， 以 氯仿 为溶剂， 以50%的产率得到N-acetylamino-N'-di-(tert-butyloxycarbonyl)guanidinohexanoic acid [2-(4-sulfamoylphenyl)ethyl]amide
  参考文献：
  名称：

  Sulfonamides with Potent Inhibitory Action and Selectivity against the α-Carbonic Anhydrase from Vibrio cholerae

  摘要：

  By using N-alpha-acetyl-L-lysine or GABA scaffolds and the conversion of the terminal amino group to the guanidine one, benzenesulfonamides incorporating water solubilizing moieties were synthesized. The new compounds were medium potency inhibitors of the cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isoforms I and II, and highly effective, nanomolar inhibitors of the pathogenic bacterial alpha-CA from Vibrio cholerae. These sulfonamides possess good selectivity for inhibiting the bacterial over the mammalian isoforms and may be used as tools to understand the role of bacterial CAs in pathogenesis.

  DOI：

  10.1021/ml500192a