N-(3,4-dimethoxyphenethyl)-3-((4-methylphenyl)sulfonamido)benzamide

• 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: N-(3,4-dimethoxyphenethyl)-3-((4-methylphenyl)sulfonamido)benzamide
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]-3-[(4-methylphenyl)sulfonylamino]benzamide
• 化学式: C₂₄H₂₆N₂O₅S
• 分子量: 454.547
• InChiKey: ZEDHRELSBPOIDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对甲苯磺酰氯 在 sodium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.4h， 生成 N-(3,4-dimethoxyphenethyl)-3-((4-methylphenyl)sulfonamido)benzamide
  参考文献：
  名称：

  Design, synthesis and biological activity of N-(3-substituted-phenyl)benzenesulfonamides as selective and reversible LSD1 inhibitors

  摘要：

  Lysine specific demethylase 1 plays a crucial role in regulating histone methylation at residues K4 and K9 on histone H3 and over-expresses in a variety of cancers. Here we designed, synthesized and evaluated a series of N-(3-substituted-phenyl)benzenesulfonamides as reversible lysine specific demethylase 1 inhibitors. All the compounds exhibited lysine specific demethylase 1 inhibition with the half maximal inhibitory concentration (IC50) values between 7.5 and 68 mu M. Three most active compounds 2a, 2c and 2i displayed only modest effect on flavin adenine dinucleotide-dependent enzymes mono-amine oxidases A and B, and their reversibilities of lysine specific demethylase 1 inhibition were confirmed. Molecular docking was also carried out to predict the binding mode of 2a into the active site of lysine specific demethylase 1. Taken together, N-(3-substituted-phenyl)benzenesulfonamides including 2a represent a new class of selective and reversible lysine specific demethylase 1 inhibitors with pharmaceutical research.

  DOI：

  10.1007/s00044-016-1706-8