toluene-4-sulfonic acid 4-(3-nitrobenzylamino)phenyl ester | 1351762-61-2

• 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: toluene-4-sulfonic acid 4-(3-nitrobenzylamino)phenyl ester
• 英文别名: [4-[(3-Nitrophenyl)methylamino]phenyl] 4-methylbenzenesulfonate；[4-[(3-nitrophenyl)methylamino]phenyl] 4-methylbenzenesulfonate
• CAS: 1351762-61-2
• 化学式: C₂₀H₁₈N₂O₅S
• 分子量: 398.439
• InChiKey: GFPOAUKLSBIWIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对甲苯磺酰氯 在 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 toluene-4-sulfonic acid 4-(3-nitrobenzylamino)phenyl ester
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of sulfonic acid ester and benzenesulfonamide derivatives as potential CETP inhibitors

  摘要：

  Epidemiological studies have established an inverse relationship between plasma high-density lipoprotein (HDL) cholesterol concentration, and incidence of coronary artery disease (CAD); thus, the development of novel therapies that attempt to exploit the atheroprotective functions of HDL is a major goal. Inhibition of cholesteryl ester transfer protein (CETP) is one of the approaches targeted to increase HDL cholesterol concentration. CETP is a glycoprotein involved in transporting lipoprotein particles and neutral lipids between HDL and low-density lipoproteins (LDL), and therefore CETP inhibitors could be useful agents in the future for treating dyslipidemia and related disorders. Guided by our previously reported pharmacophore and QSAR models for CETP inhibition, we synthesized and bioassayed a series of sulfonic acid ester and benzenesulfonamide derivatives that can serve as a promising lead compounds for the development of potential and selective CETP inhibitors. The most potent compound 6k illustrated an IC50 of 3.4 mu M.

  DOI：

  10.1007/s00044-011-9917-5

文献信息

• Design, synthesis, and biological evaluation of sulfonic acid ester and benzenesulfonamide derivatives as potential CETP inhibitors
  作者：Reema Abu Khalaf、Ghassan Abu Sheikha、Mahmoud Al-Sha’er、Ghadeer Albadawi、Mutasem Taha

  DOI：10.1007/s00044-011-9917-5

  日期：2012.11

  Epidemiological studies have established an inverse relationship between plasma high-density lipoprotein (HDL) cholesterol concentration, and incidence of coronary artery disease (CAD); thus, the development of novel therapies that attempt to exploit the atheroprotective functions of HDL is a major goal. Inhibition of cholesteryl ester transfer protein (CETP) is one of the approaches targeted to increase HDL cholesterol concentration. CETP is a glycoprotein involved in transporting lipoprotein particles and neutral lipids between HDL and low-density lipoproteins (LDL), and therefore CETP inhibitors could be useful agents in the future for treating dyslipidemia and related disorders. Guided by our previously reported pharmacophore and QSAR models for CETP inhibition, we synthesized and bioassayed a series of sulfonic acid ester and benzenesulfonamide derivatives that can serve as a promising lead compounds for the development of potential and selective CETP inhibitors. The most potent compound 6k illustrated an IC50 of 3.4 mu M.