4-oxo-4-((4-sulfamoylbenzyl)amino)butan-1-aminium chloride | 1610892-98-2

• 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-oxo-4-((4-sulfamoylbenzyl)amino)butan-1-aminium chloride
• 英文别名: 4-amino-N-(4-sulfamoylbenzyl)butyramide hydrochloride；4-amino-N-[(4-sulfamoylphenyl)methyl]butanamide;hydrochloride
• CAS: 1610892-98-2
• 化学式: C₁₁H₁₇N₃O₃S*ClH
• 分子量: 307.801
• InChiKey: DXUUDRQDZTZFHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.11
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  tert-butyl (4-oxo-4((4-sulfamoylbenzyl)amino)butyl)carbamate 在 盐酸 作用下， 以 水 为溶剂， 以100%的产率得到4-oxo-4-((4-sulfamoylbenzyl)amino)butan-1-aminium chloride
  参考文献：
  名称：

  结合有GABA部分的新型脲基取代磺酰胺对人碳酸酐酶同工型I–XIV的抑制作用研究

  摘要：

  γ-BOC-GABA的反应中，通过保护氨基丁酸的γ-氨基部分与制备叔-丁氧基羰基（Boc）保护基，与4-甲基/乙基苯磺酰胺结合，然后在3 M HCl中除去Boc保护基，得到相应的盐酸盐，将其与不同种类的芳基异氰酸酯反应进一步衍生化，得到新的类别含有GABA部分的脲基取代的苯磺酰胺的制备。用这些新化合物对人碳酸酐酶（CA，EC 4.2.1.1）同工型，CA I–XIV的抑制研究表明，它们对hCA III，IV，VA，VI和XIII具有中等至弱的抑制能力，相当有效的抑制能力对hCA I，VI和IX具有抗性，并且对生理相关的hCA II和VII以及两种与肿瘤相关的同工型CA IX和XII具有出色的抑制作用。

  DOI：

  10.1016/j.bmc.2014.10.041

文献信息

• Synthesis and inhibition potency of novel ureido benzenesulfonamides incorporating GABA as tumor-associated carbonic anhydrase IX and XII inhibitors
  作者：Mariangela Ceruso、Sabrina Antel、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.3109/14756366.2015.1014477

  日期：2016.3.3

  New ureido benzenesulfonamides incorporating a GABA moiety as a linker between the ureido and the sulfonamide functionalities were synthesized and their inhibition potency determined against both the predominant cytosolic (hCA I and II) and the transmembrane tumor-associated (hCA IX and XII) isoforms of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). The majority of these compounds were medium potency inhibitors of the cytosolic isoform hCA I and effective hCA II inhibitors, whereas they showed strong inhibition of the two transmembrane tumor-associated isoforms hCA IX and XII, with K(I)s in nanomolar range. Only one derivative had a good selectivity for inhibition of the tumor-associated hCA IX target isoform over the cytosolic and physiologically dominant off-target hCA I and II, being thus a potential tool to develop new anticancer agents.
• 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.
• Inhibition studies of new ureido-substituted sulfonamides incorporating a GABA moiety against human carbonic anhydrase isoforms I–XIV
  作者：Mariangela Ceruso、Sabrina Antel、Daniela Vullo、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2014.10.041

  日期：2014.12

  γ-Boc-GABA, prepared by protecting the γ-amino moiety of the amino butyric acid with the tert-butyloxycarbonyl (Boc) protecting group, with 4-methyl/ethyl benzenesulfonamide, followed by removal of the Boc protecting group in 3 M HCl afforded the corresponding hydrochlorides, which were further derivatized by reaction with a varying of aryl isocyanates to give a new classes of ureido substituted benzenesulfonamide

  γ-BOC-GABA的反应中，通过保护氨基丁酸的γ-氨基部分与制备叔-丁氧基羰基（Boc）保护基，与4-甲基/乙基苯磺酰胺结合，然后在3 M HCl中除去Boc保护基，得到相应的盐酸盐，将其与不同种类的芳基异氰酸酯反应进一步衍生化，得到新的类别含有GABA部分的脲基取代的苯磺酰胺的制备。用这些新化合物对人碳酸酐酶（CA，EC 4.2.1.1）同工型，CA I–XIV的抑制研究表明，它们对hCA III，IV，VA，VI和XIII具有中等至弱的抑制能力，相当有效的抑制能力对hCA I，VI和IX具有抗性，并且对生理相关的hCA II和VII以及两种与肿瘤相关的同工型CA IX和XII具有出色的抑制作用。