[1-[(2,4-dichlorophenyl)methyl]-3,4-dihydro-2H-quinolin-6-yl] N-hexylcarbamate | 1402151-38-5

• 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: [1-[(2,4-dichlorophenyl)methyl]-3,4-dihydro-2H-quinolin-6-yl] N-hexylcarbamate
• CAS: 1402151-38-5
• 化学式: C₂₃H₂₈Cl₂N₂O₂
• 分子量: 435.394
• InChiKey: MMQHCPQYOVXZBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-甲氧基喹啉 在 nickel-aluminum alloy 、 三溴化硼 、 potassium carbonate 、 三乙胺 、 potassium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 [1-[(2,4-dichlorophenyl)methyl]-3,4-dihydro-2H-quinolin-6-yl] N-hexylcarbamate
  参考文献：
  名称：

  Lead optimization studies towards the discovery of novel carbamates as potent AChE inhibitors for the potential treatment of Alzheimer’s disease

  摘要：

  The optimization of our previous lead compound 1 (AChE IC50 = 3.31 mu M) through synthesis and pharmacology of a series of novel carbamates is reported. The synthesized compounds were evaluated against mouse brain AChE enzyme using the colorimetric method described by Ellman et al. The three compounds 6a (IC50 = 2.57 mu M), 6b (IC50 = 0.70 mu M) and 6i (IC50 = 2.56 mu M) exhibited potent in vitro AChE inhibitory activities comparable to the drug rivastigmine (IC50= 1.11 mu M). Among them, the compound 6b has been selected as possible optimized lead for further neuropharmacological studies. In addition, the AChE-carbamate Michaelis complexes of these potent compounds including rivastigmine and ganstigmine have been modeled using covalent docking protocol of GOLD and important direct/indirect interactions contributing to stabilization of the AChE-carbamate Michaelis complexes have been investigated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.005

文献信息

• Lead optimization studies towards the discovery of novel carbamates as potent AChE inhibitors for the potential treatment of Alzheimer’s disease
  作者：Kuldeep K. Roy、Santoshkumar Tota、Tusha Tripathi、Subhash Chander、Chandishwar Nath、Anil K. Saxena

  DOI：10.1016/j.bmc.2012.09.005

  日期：2012.11

  The optimization of our previous lead compound 1 (AChE IC50 = 3.31 mu M) through synthesis and pharmacology of a series of novel carbamates is reported. The synthesized compounds were evaluated against mouse brain AChE enzyme using the colorimetric method described by Ellman et al. The three compounds 6a (IC50 = 2.57 mu M), 6b (IC50 = 0.70 mu M) and 6i (IC50 = 2.56 mu M) exhibited potent in vitro AChE inhibitory activities comparable to the drug rivastigmine (IC50= 1.11 mu M). Among them, the compound 6b has been selected as possible optimized lead for further neuropharmacological studies. In addition, the AChE-carbamate Michaelis complexes of these potent compounds including rivastigmine and ganstigmine have been modeled using covalent docking protocol of GOLD and important direct/indirect interactions contributing to stabilization of the AChE-carbamate Michaelis complexes have been investigated. (C) 2012 Elsevier Ltd. All rights reserved.