4-[2-(4-chlorophenyl)acetamidoethyl]benzenesulfonamide | 25210-79-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[2-(4-chlorophenyl)acetamidoethyl]benzenesulfonamide
• 英文别名: 2-(4-chlorophenyl)-N-[2-(4-sulfamoylphenyl)ethyl]acetamide
• CAS: 25210-79-1
• 化学式: C₁₆H₁₇ClN₂O₃S
• mdl: MFCD02862446
• 分子量: 352.842
• InChiKey: GWTJPQWQEBUCJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氯苯乙酰氯 、 4-(2-氨乙基)苯磺酰胺 在 三乙胺 作用下， 以 乙腈 为溶剂， 以52%的产率得到4-[2-(4-chlorophenyl)acetamidoethyl]benzenesulfonamide
  参考文献：
  名称：

  A Class of Sulfonamides with Strong Inhibitory Action against the α-Carbonic Anhydrase from Trypanosoma cruzi

  摘要：

  Trypanosoma cruzi, the causative agent of Chagas disease, encodes for an alpha-carbonic anhydrase (CA, EC 4.2.1.1) possessing high catalytic activity (TcCA) which was recently characterized (Pan et al. J. Med. Chem. 2013, 56, 1761-1771). A new class of sulfonamides possessing low nanomolar/subnanomolar TcCA inhibitory activity is described here. Aromatic/heterocydic sulfonamides incorporating halogeno/methoxyphenacetamido tails inhibited TcCA with K(I)s in the range of 0.5-12.5 nM, being less effective against the human off-target isoforms hCA I and II. A homology model of TcCA helped us to rationalize the excellent inhibition profile of these compounds against the protozoan enzyme, a putative new antitrypanosoma drug target. These compounds were ineffective antitrypanosomal agents in vivo due to penetrability problems of these highly polar molecules that possess sulfonamide moieties.

  DOI：

  10.1021/jm400418p

文献信息

• COMPOUNDS THAT INHIBIT HUMAN DNA LIGASES AND METHODS OF TREATING CANCER
  申请人：TOMKINSON Alan E.

  公开号：US20100099683A1

  公开（公告）日：2010-04-22

  Methods for treating cancer using compounds that inhibit human DNA ligases. Methods for using compounds that inhibit human DNA ligases to provide insights into the reaction mechanisms of human DNA ligases, for example to identify the human DNA ligase involved in different DNA repair pathways. Screening methods for compounds that inhibit human DNA ligases.
• US8445537B2
  申请人：——

  公开号：US8445537B2

  公开（公告）日：2013-05-21
• A Class of Sulfonamides with Strong Inhibitory Action against the α-Carbonic Anhydrase from <i>Trypanosoma cruzi</i>
  作者：Özlen Güzel-Akdemir、Atilla Akdemir、Peiwen Pan、Alane B. Vermelho、Seppo Parkkila、Andrea Scozzafava、Clemente Capasso、Claudiu T. Supuran

  DOI：10.1021/jm400418p

  日期：2013.7.25

  Trypanosoma cruzi, the causative agent of Chagas disease, encodes for an alpha-carbonic anhydrase (CA, EC 4.2.1.1) possessing high catalytic activity (TcCA) which was recently characterized (Pan et al. J. Med. Chem. 2013, 56, 1761-1771). A new class of sulfonamides possessing low nanomolar/subnanomolar TcCA inhibitory activity is described here. Aromatic/heterocydic sulfonamides incorporating halogeno/methoxyphenacetamido tails inhibited TcCA with K(I)s in the range of 0.5-12.5 nM, being less effective against the human off-target isoforms hCA I and II. A homology model of TcCA helped us to rationalize the excellent inhibition profile of these compounds against the protozoan enzyme, a putative new antitrypanosoma drug target. These compounds were ineffective antitrypanosomal agents in vivo due to penetrability problems of these highly polar molecules that possess sulfonamide moieties.