4-(4-氯苄基氨基)苯磺酰胺 | 1019511-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-氯苄基氨基)苯磺酰胺
• 英文名称: 4-((4-chlorobenzyl)amino)benzenesulfonamide
• 英文别名: 4-[(4-Chlorophenyl)methylamino]benzenesulfonamide
• CAS: 1019511-09-1
• 化学式: C₁₃H₁₃ClN₂O₂S
• 分子量: 296.777
• InChiKey: WDQRETMIHDJBNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-氯苄基氨基)苯磺酰胺 、 1,1,1-trifluoro-4-iso-butoxy-3-buten-2-one 以 乙腈 为溶剂， 反应 16.0h， 以78%的产率得到4-[4-chlorobenzyl-((E)-4,4,4-trifluoro-3-oxo-but-1-enyl)amino]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and carbonic anhydrase I, II, IX and XII inhibition studies of 4-N,N-disubstituted sulfanilamides incorporating 4,4,4-trifluoro-3-oxo-but-1-enyl, phenacylthiourea and imidazol-2(3H)-one/thione moieties

  摘要：

  A series of sulfonamides incorporating the sulfanilamide ( SA) scaffold were prepared. Reaction of the 4-amino moiety of SA with benzyl chlorides or substituted bromoacetophenones afforded the derivatives which were then reacted with 1,1,1-trifluoro-4-isobutoxybut-3-en-2-one leading to a series of 4-N,N-disubstituted SAs. The key intermediates were also reacted with ethoxycarbonyl isothiocyanate leading to thioureas or were cyclized in the presence of potassium cyanate/isothiocyanate to the corresponding imidazol-2(3H)-one/thiones. The new compounds were tested as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic CA I and II, and the transmembrane, tumor-associated CA IX and XII. These sulfonamides were ineffective CA I and II inhibitors but were nanomolar CA IX and XII inhibitors, making them of interest as clinical candidates for antitumor/antimetastasis applications. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.030
• 作为产物：
  描述：

  4-氯氯苄 、 磺胺 在 calcium carbonate 作用下， 以 水 为溶剂， 反应 3.0h， 以97%的产率得到4-(4-氯苄基氨基)苯磺酰胺
  参考文献：
  名称：

  Synthesis and carbonic anhydrase I, II, IX and XII inhibition studies of 4-N,N-disubstituted sulfanilamides incorporating 4,4,4-trifluoro-3-oxo-but-1-enyl, phenacylthiourea and imidazol-2(3H)-one/thione moieties

  摘要：

  A series of sulfonamides incorporating the sulfanilamide ( SA) scaffold were prepared. Reaction of the 4-amino moiety of SA with benzyl chlorides or substituted bromoacetophenones afforded the derivatives which were then reacted with 1,1,1-trifluoro-4-isobutoxybut-3-en-2-one leading to a series of 4-N,N-disubstituted SAs. The key intermediates were also reacted with ethoxycarbonyl isothiocyanate leading to thioureas or were cyclized in the presence of potassium cyanate/isothiocyanate to the corresponding imidazol-2(3H)-one/thiones. The new compounds were tested as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic CA I and II, and the transmembrane, tumor-associated CA IX and XII. These sulfonamides were ineffective CA I and II inhibitors but were nanomolar CA IX and XII inhibitors, making them of interest as clinical candidates for antitumor/antimetastasis applications. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.030

文献信息

• Optimization of 4‐Substituted Benzenesulfonamide Scaffold To Reverse <i>Acinetobacter baumannii</i> Serum‐Adaptive Efflux Associated Antibiotic Tolerance
  作者：Michaelle Chojnacki、Xufeng Cao、Mikaeel Young、Rebecca N. Fritz、Paul M. Dunman、Daniel P. Flaherty

  DOI：10.1002/cmdc.202000328

  日期：2020.9.16

  susceptible to antibiotic therapy. Previously, we identified a sulfonamide‐containing scaffold molecule (ABEPI1) that reversed serum‐associated antibiotic tolerance in A. baumannii. Herein, we present structure‐activity relationship studies on 29 newly synthesized analogues. These molecules were characterized for their ability to potentiate multiple antibiotics in serum, reduce serum‐associated ethidium

  由于多药和全药耐药率不断上升，鲍曼不动杆菌是一种急需公共卫生关注的院内病原体。在人血清中生长等环境因素的背景下，已知鲍曼不动杆菌显示适应性外排，其中大量外排相关基因被上调，导致外排介导的耐药菌株对抗生素敏感治疗。以前，我们发现了一种含有磺酰胺的支架分子（ABEPI1），可以逆转鲍曼不动杆菌血清相关的抗生素耐受性. 在此，我们对 29 种新合成的类似物进行构效关系研究。这些分子的特征在于它们能够增强血清中的多种抗生素，减少血清相关的溴化乙锭外流并使细菌细胞膜去极化。此外，还评估了它们对哺乳动物细胞的毒性。总的来说，这些分子可能代表了与新的和现有的抗生素联合使用来治疗鲍曼不动杆菌细菌感染的有前景的潜在佐剂。
• Synthesis and carbonic anhydrase I, II, IX and XII inhibition studies of 4-N,N-disubstituted sulfanilamides incorporating 4,4,4-trifluoro-3-oxo-but-1-enyl, phenacylthiourea and imidazol-2(3H)-one/thione moieties
  作者：Cenzo Congiu、Valentina Onnis、Gianfranco Balboni、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2014.02.030

  日期：2014.4

  A series of sulfonamides incorporating the sulfanilamide ( SA) scaffold were prepared. Reaction of the 4-amino moiety of SA with benzyl chlorides or substituted bromoacetophenones afforded the derivatives which were then reacted with 1,1,1-trifluoro-4-isobutoxybut-3-en-2-one leading to a series of 4-N,N-disubstituted SAs. The key intermediates were also reacted with ethoxycarbonyl isothiocyanate leading to thioureas or were cyclized in the presence of potassium cyanate/isothiocyanate to the corresponding imidazol-2(3H)-one/thiones. The new compounds were tested as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic CA I and II, and the transmembrane, tumor-associated CA IX and XII. These sulfonamides were ineffective CA I and II inhibitors but were nanomolar CA IX and XII inhibitors, making them of interest as clinical candidates for antitumor/antimetastasis applications. (C) 2014 Elsevier Ltd. All rights reserved.