4-(3-(4-nitrophenyl)ureido)-N-(4-sulfamoylphenethyl)butanamide

• 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-(3-(4-nitrophenyl)ureido)-N-(4-sulfamoylphenethyl)butanamide
• 英文别名: 4-[(4-nitrophenyl)carbamoylamino]-N-[2-(4-sulfamoylphenyl)ethyl]butanamide
• 化学式: C₁₉H₂₃N₅O₆S
• 分子量: 449.488
• InChiKey: GIXRHINNRGUEBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  185
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(2-氨乙基)苯磺酰胺 在 盐酸 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 生成 4-(3-(4-nitrophenyl)ureido)-N-(4-sulfamoylphenethyl)butanamide
  参考文献：
  名称：

  Synthesis and inhibition potency of novel ureido benzenesulfonamides incorporating GABA as tumor-associated carbonic anhydrase IX and XII inhibitors

  摘要：

  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.

  DOI：

  10.3109/14756366.2015.1014477

文献信息

• 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。
• 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.