4-[2-amino-3-cyano-4-(2-hydroxynaphthalen-1-yl)-5,6,7,8-tetrahydroquinolin-1(4H)-yl]benzenesulfonamide | 1234708-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-[2-amino-3-cyano-4-(2-hydroxynaphthalen-1-yl)-5,6,7,8-tetrahydroquinolin-1(4H)-yl]benzenesulfonamide
• 英文别名: 4-[2-amino-3-cyano-4-(2-hydroxynaphthalen-1-yl)-5,6,7,8-tetrahydro-4H-quinolin-1-yl]benzenesulfonamide
• CAS: 1234708-34-9
• 化学式: C₂₆H₂₄N₄O₃S
• 分子量: 472.568
• InChiKey: YQRVRFRLPSGVPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(cyclohexenylamino)benzenesulfonamide 、 2-羟基-1-萘甲醛 、 丙二腈 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 4-[2-amino-3-cyano-4-(2-hydroxynaphthalen-1-yl)-5,6,7,8-tetrahydroquinolin-1(4H)-yl]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and in vitro anticancer screening of some novel 4-[2-amino-3-cyano-4-substituted-5,6,7,8-tetrahydroquinolin-1-(4H)-yl]benzenesulfonamides

  摘要：

  It has been reported that aryl/heteroaryl sulfonamide compounds may act as anticancer agents through a variety of mechanisms and the most prominent of these mechanisms is through the inhibition of carbonic anhydrase isozymes. The present work reports the possible utility of 4-(cyclohexenylamino) benzenesulfonamide in the synthesis of some novel 4-(quinolin-1-yl)benzenesulfonamide derivatives 6a-u. The structures of these compounds were confirmed by elemental analyses, IR, (1)H NMR and mass spectral data. All the newly synthesized compounds were evaluated for their in vitro anticancer activity. Some compounds showed interesting in vitro anticancer activities when compared with doxorubicin as a reference drug. In addition, docking of the synthesized compounds into carbonic anhydrase isozyme II (CA II) active site was performed in order to give a suggestion about the proposed mechanism of action. (c) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.030

文献信息

• Synthesis and in vitro anticancer screening of some novel 4-[2-amino-3-cyano-4-substituted-5,6,7,8-tetrahydroquinolin-1-(4H)-yl]benzenesulfonamides
  作者：Mansour S. Al-Said、Mostafa M. Ghorab、Saleh I. Al-qasoumi、Ebaa M. El-Hossary、Eman Noaman

  DOI：10.1016/j.ejmech.2010.03.030

  日期：2010.7

  It has been reported that aryl/heteroaryl sulfonamide compounds may act as anticancer agents through a variety of mechanisms and the most prominent of these mechanisms is through the inhibition of carbonic anhydrase isozymes. The present work reports the possible utility of 4-(cyclohexenylamino) benzenesulfonamide in the synthesis of some novel 4-(quinolin-1-yl)benzenesulfonamide derivatives 6a-u. The structures of these compounds were confirmed by elemental analyses, IR, (1)H NMR and mass spectral data. All the newly synthesized compounds were evaluated for their in vitro anticancer activity. Some compounds showed interesting in vitro anticancer activities when compared with doxorubicin as a reference drug. In addition, docking of the synthesized compounds into carbonic anhydrase isozyme II (CA II) active site was performed in order to give a suggestion about the proposed mechanism of action. (c) 2010 Elsevier Masson SAS. All rights reserved.