4-(2-(4-chlorophenyl)-2-oxoethylamino)benzenesulfonamide | 1595285-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2-(4-chlorophenyl)-2-oxoethylamino)benzenesulfonamide
• 英文别名: 4-(4-chlorophenacylamino)benzenesulfonamide
• CAS: 1595285-55-4
• 化学式: C₁₄H₁₃ClN₂O₃S
• 分子量: 324.788
• InChiKey: VZVUHHPSHVRUTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 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：
  0.07
• 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-(2-(4-chlorophenyl)-2-oxoethylamino)benzenesulfonamide 在 sodium ethanolate 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 34.0h， 生成 4-(5-(4-chlorophenyl)-4-(m-tolylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)benzenesulfonamide
  参考文献：
  名称：

  Pyrrolo and pyrrolopyrimidine sulfonamides act as cytotoxic agents in hypoxia via inhibition of transmembrane carbonic anhydrases

  摘要：

  A series of novel sulfonamide derivatives bearing pyrrole and pyrrolopyrimidine scaffolds were synthesized and screened as carbonic anhydrase inhibitors. The inhibition activity of the synthesized compounds was evaluated against the cytosolic human carbonic anhydrase isoforms I and II and the transmembranal isoforms IX and XII. Several candidates showed potent inhibitory activity against IX and XII isoforms. Furthermore, ex vivo screening of cytotoxic selectivity and activity of the most potent derivatives were carried out against normal cells (WI38) and cervical cancer cell line (HeLa) under normal and hypoxic conditions using acetazolamide as reference drug. Compound 11b potency was nearly three folds higher in hypoxic than normoxic condition whereas that of compound 11f was nearly four folds higher in hypoxic vs. normoxic HeLa cells. All the screened derivatives exhibited less potency on normal cells (WI38). Molecular docking was carried out to discover the possible binding mode of compounds within the active site of isoform CA IX. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.112021
• 作为产物：
  描述：

  磺胺 、 2'-溴-4-氯苯乙酮 以 甲醇 为溶剂， 反应 4.0h， 以89%的产率得到4-(2-(4-chlorophenyl)-2-oxoethylamino)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