(E)-N-hydroxy-3-(2-((4-methoxyphenyl)sulfonyl)quinolin-3-yl)acrylamide

• 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: (E)-N-hydroxy-3-(2-((4-methoxyphenyl)sulfonyl)quinolin-3-yl)acrylamide
• 英文别名: (E)-N-hydroxy-3-[2-(4-methoxyphenyl)sulfonylquinolin-3-yl]prop-2-enamide
• 化学式: C₁₉H₁₆N₂O₅S
• 分子量: 384.412
• InChiKey: KIFDIACFECYMKV-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-溴-2-氯喹啉 在 tris-(dibenzylideneacetone)dipalladium(0) 、 O-(四氢-2H-吡喃-2-基)羟基胺 、 N-甲基二环己基胺 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间氯过氧苯甲酸 、 三氟乙酸 、 tris[tert-butyl]phosphonium tetrafluoroborate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 (E)-N-hydroxy-3-(2-((4-methoxyphenyl)sulfonyl)quinolin-3-yl)acrylamide
  参考文献：
  名称：

  2-(Phenylsulfonyl)quinoline N -hydroxyacrylamides as potent anticancer agents inhibiting histone deacetylase

  摘要：

  This study reports the design and synthesis of 2-(phenylsulfonyl)quinoline N-hydroxyacrylamides (8a-k). Structure-activity relationship studies focusing on regio-effect of N-hydroxyacrylamide moiety and influence of the sulfonyl linker revealed that N-hydroxy-3-[3-(quinoline-2-sulfonyl)-phenyl]-acrylamide (8f) showed remarkable enzymatic and cellular activity. The GI(50) values of 8f for HL-60, HCT116, PC-3, and A549 cells were found to be 0.29, 0.08, 0.15, and 0.27 mu M, respectively. The compounds are therefore more potent than FDA approved PXD-101 and SAHA. They also have an effect on the acetylation degree of histone H3 and alpha-tubulin. In in vivo studies, 8f showed marked inhibition of the growth of HCT116 xenografts. (C) 2016 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2016.06.023

文献信息

• 2-(Phenylsulfonyl)quinoline N -hydroxyacrylamides as potent anticancer agents inhibiting histone deacetylase
  作者：Hsueh-Yun Lee、Chih-Yi Chang、Chih-Jou Su、Han-Li Huang、Samir Mehndiratta、Yuh-Hsuan Chao、Chia-Ming Hsu、Sunil Kumar、Ting-Yi Sung、Yi-Zhen Huang、Yu-Hsuan Li、Chia-Ron Yang、Jing-Ping Liou

  DOI：10.1016/j.ejmech.2016.06.023

  日期：2016.10

  This study reports the design and synthesis of 2-(phenylsulfonyl)quinoline N-hydroxyacrylamides (8a-k). Structure-activity relationship studies focusing on regio-effect of N-hydroxyacrylamide moiety and influence of the sulfonyl linker revealed that N-hydroxy-3-[3-(quinoline-2-sulfonyl)-phenyl]-acrylamide (8f) showed remarkable enzymatic and cellular activity. The GI(50) values of 8f for HL-60, HCT116, PC-3, and A549 cells were found to be 0.29, 0.08, 0.15, and 0.27 mu M, respectively. The compounds are therefore more potent than FDA approved PXD-101 and SAHA. They also have an effect on the acetylation degree of histone H3 and alpha-tubulin. In in vivo studies, 8f showed marked inhibition of the growth of HCT116 xenografts. (C) 2016 Published by Elsevier Masson SAS.