2-isopropyl-5-methylphenyl naphthalen-1-ylcarbamate | 6275-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-isopropyl-5-methylphenyl naphthalen-1-ylcarbamate
• 英文别名: [1]naphthyl-carbamic acid-(2-isopropyl-5-methyl-phenyl ester)；[1]Naphthyl-carbamidsaeure-(2-isopropyl-5-methyl-phenylester)；α-Naphthyl-carbamidsaeure-thymylester；Naphthyl-(1)-carbamidsaeure-thymylester；5-Methyl-2-(propan-2-yl)phenyl naphthalen-1-ylcarbamate；(5-methyl-2-propan-2-ylphenyl) N-naphthalen-1-ylcarbamate
• CAS: 6275-64-5
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: JXDUPHZQYZPGDN-UHFFFAOYSA-N

物化性质

• 沸点：
  459.8±45.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  百里酚 、 1-Alapha-萘异氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以85%的产率得到2-isopropyl-5-methylphenyl naphthalen-1-ylcarbamate
  参考文献：
  名称：

  Synthesis, anticholinesterase activity and molecular modeling study of novel carbamate-substituted thymol/carvacrol derivatives

  摘要：

  New thymol and carvacrol derivatives with the carbamate moiety were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 5-isopropyl-2-methylphenyl(3-fluorophenyl)carbamate (29) was found to be the most potent AChE inhibitor with IC50 values of 2.22 mu M, and 5-isopropyl-2-methylphenyl (4-fluorophenyl)carbamate (30) exhibited the strongest inhibition against BuChE with IC50 value of 0.02 mu M. Additionally, the result of H4IIE hepatoma cell toxicity assay for compounds 18, 20, 29, 30 and 35 showed negligible cell death at 0.07-10 mu M. Moreover in order to better understand the inhibitory profiles of these molecules, molecular modeling studies were applied. Binding poses of studied compounds at the binding pockets of AChE and BuChE targets were determined. Predicted binding energies of these compounds as well as structural and dynamical profiles of molecules at the target sites were estimated using induced fit docking (IFD) algorithms and post-processing molecular dynamics (MD) simulations methods (i.e., Molecular mechanics Poisson-Boltzmann surface area (MM-PBSA) approaches). (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.12.037

文献信息

• Synthesis, anticholinesterase activity and molecular modeling study of novel carbamate-substituted thymol/carvacrol derivatives
  作者：Belma Zengin Kurt、Isil Gazioglu、Aydan Dag、Ramin Ekhteiari Salmas、Gülru Kayık、Serdar Durdagi、Fatih Sonmez

  DOI：10.1016/j.bmc.2016.12.037

  日期：2017.2

  New thymol and carvacrol derivatives with the carbamate moiety were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 5-isopropyl-2-methylphenyl(3-fluorophenyl)carbamate (29) was found to be the most potent AChE inhibitor with IC50 values of 2.22 mu M, and 5-isopropyl-2-methylphenyl (4-fluorophenyl)carbamate (30) exhibited the strongest inhibition against BuChE with IC50 value of 0.02 mu M. Additionally, the result of H4IIE hepatoma cell toxicity assay for compounds 18, 20, 29, 30 and 35 showed negligible cell death at 0.07-10 mu M. Moreover in order to better understand the inhibitory profiles of these molecules, molecular modeling studies were applied. Binding poses of studied compounds at the binding pockets of AChE and BuChE targets were determined. Predicted binding energies of these compounds as well as structural and dynamical profiles of molecules at the target sites were estimated using induced fit docking (IFD) algorithms and post-processing molecular dynamics (MD) simulations methods (i.e., Molecular mechanics Poisson-Boltzmann surface area (MM-PBSA) approaches). (C) 2016 Elsevier Ltd. All rights reserved.