4-(4-methylphenacylamino)benzenesulfonamide | 1595285-57-6

• 英文名称: 4-(4-methylphenacylamino)benzenesulfonamide
• 英文别名: 4-((2-oxo-2-(p-tolyl)ethyl)amino)benzenesulfonamide；4-[[2-(4-Methylphenyl)-2-oxoethyl]amino]benzenesulfonamide
• CAS: 1595285-57-6
• 化学式: C₁₅H₁₆N₂O₃S
• 分子量: 304.37
• InChiKey: YDOBLHNGDZEPIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  89.26
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(4-methylphenacylamino)benzenesulfonamide 、 1,1,1-trifluoro-4-iso-butoxy-3-buten-2-one 以 乙腈 为溶剂， 反应 16.0h， 以81%的产率得到4-[[2-(4-methylphenyl)-2-oxoethyl]-[(E)-4,4,4-trifluoro-3-oxobut-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：

  磺胺 、 2-溴-4'-甲基苯乙酮 以 甲醇 为溶剂， 反应 4.0h， 以98%的产率得到4-(4-methylphenacylamino)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

文献信息

• Insertion of metal carbenes into the anilinic N–H bond of unprotected aminobenzenesulfonamides delivers low nanomolar inhibitors of human carbonic anhydrase IX and XII isoforms
  作者：Tatiana Sharonova、Polina Paramonova、Stanislav Kalinin、Alexander Bunev、Rovshan Е. Gasanov、Alessio Nocentini、Vladimir Sharoyko、Tatiana B. Tennikova、Dmitry Dar’in、Claudiu T. Supuran、Mikhail Krasavin

  DOI：10.1016/j.ejmech.2021.113352

  日期：2021.6

  primary sulfonamides generated via formal N–H-insertion of metal carbenes into anilinic amino group of sulfanilamide and its meta-substituted analog. Obtained compounds were tested in vitro as inhibitors of four physiologically significant isoforms of the metalloenzyme human carbonic anhydrase (hCA, EC 4.2.1.1). Many of the synthesized sulfonamides displayed low nanomolar Ki values against therapeutically

  在本文中，我们报告了一组 34 种伯磺酰胺的合成，这些磺酰胺是通过将金属卡宾正式N - H插入磺胺及其间位取代类似物的苯胺氨基中而产生的。获得的化合物作为金属酶人碳酸酐酶 ( h CA, EC 4.2.1.1)的四种生理学显着同工型的抑制剂在体外进行了测试。许多合成的磺胺类药物对治疗相关的h CA II、IX 和 XII显示出低纳摩尔 K i值，而它们不能有效抑制hCA I. 提供物质对肿瘤相关h CA IX 和 XII 同工酶的有希望的活性谱，对整个组进行单浓度 MTT 测试。令人失望的是，大多数发现的h CA 抑制剂在常氧或 CoCl 2诱导的缺氧条件下都没有显着抑制癌细胞的生长。仅有的两种发挥显着抗增殖作用的化合物是适度的h CA 抑制剂。它们在细胞中超出范围的活性可能归因于迈克尔受体亚结构的存在，该亚结构可能通过抑制硫氧还蛋白还原酶 (TrxRs, EC 1.8.1.9) 或与细胞蛋白质的非特异性共价结合起作用。