4-[2-amino-3-cyano-4-(4-hydroxy-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-quinolin-1-yl]benzenesulfonamide | 1019911-86-4

• 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-(4-hydroxy-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-quinolin-1-yl]benzenesulfonamide
• 英文别名: 4-[2-amino-3-cyano-4-(4-hydroxyphenyl)-5-oxo-5,6,7,8-tetrahydro-7,7-dimethyl quinolin-1(4H)-yl]benzenesulfonamide；4-[2-amino-3-cyano-4-(4-hydroxyphenyl)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-quinolin-1-yl]benzenesulfonamide
• CAS: 1019911-86-4
• 化学式: C₂₄H₂₄N₄O₄S
• 分子量: 464.545
• InChiKey: RRKIDEJCRJPQMH-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  767.6±70.0 °C(predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  159
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  磺胺 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 4-[2-amino-3-cyano-4-(4-hydroxy-phenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-quinolin-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis, and antitumor screening of certain novel tetrahydroquinoline sulfonamides

  摘要：

  Sulfonamide containing molecules are of sound biomedical interest. This work comprises the synthesis and in vitro antitumor testing of new library of 20 such molecules. These compounds were screened for cytotoxic activity against three tumor cell lines MCF-7, HeLa, and HepG2 using MTT assay. The yield was low but all the target compounds exhibited antiproliferative activity better than the standard drug Doxorubicin (CAS-23214-92-8). Seven compounds were more potent and four compounds were as active as the standard drug. There were no great difference between compounds obtained from dimedone and those obtained from cyclohexandione. Also no significant difference found in activity between compounds bearing o-amino ethyl ester side chain and compounds bearing o-amino amide derivatives. However, compounds bearing o-amino-cyano group, although retained considerable activity they were far less active than the preceding two. It was clear that monohydroxy aldehyde derivatives were less active compared with the di and trihydroxy ones.

  DOI：

  10.3109/14756366.2014.899595

文献信息

• Ghorab, Mostafa M.; Ragab, Fatma A.; Noaman, Eman, Arzneimittel-Forschung/Drug Research, 2008, vol. 58, # 1, p. 35 - 41
  作者：Ghorab, Mostafa M.、Ragab, Fatma A.、Noaman, Eman、Heiba, Helmy I.、El-Hossary, Ebaa M.

  DOI：——

  日期：——
• Design, synthesis, and antitumor screening of certain novel tetrahydroquinoline sulfonamides
  作者：Ahmed M. Alafeefy

  DOI：10.3109/14756366.2014.899595

  日期：2015.3.4

  Sulfonamide containing molecules are of sound biomedical interest. This work comprises the synthesis and in vitro antitumor testing of new library of 20 such molecules. These compounds were screened for cytotoxic activity against three tumor cell lines MCF-7, HeLa, and HepG2 using MTT assay. The yield was low but all the target compounds exhibited antiproliferative activity better than the standard drug Doxorubicin (CAS-23214-92-8). Seven compounds were more potent and four compounds were as active as the standard drug. There were no great difference between compounds obtained from dimedone and those obtained from cyclohexandione. Also no significant difference found in activity between compounds bearing o-amino ethyl ester side chain and compounds bearing o-amino amide derivatives. However, compounds bearing o-amino-cyano group, although retained considerable activity they were far less active than the preceding two. It was clear that monohydroxy aldehyde derivatives were less active compared with the di and trihydroxy ones.