5-formyl-2-methoxyphenyl dimethylcarbamate

• 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: 5-formyl-2-methoxyphenyl dimethylcarbamate
• 英文别名: 4-formyl-2-methoxyphenyl dimethylcarbamate；(5-formyl-2-methoxyphenyl) N,N-dimethylcarbamate
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: QSIRUXGVXJQXLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-formyl-2-methoxyphenyl dimethylcarbamate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以80%的产率得到5-(hydroxymethyl)-2-methoxyphenyl dimethylcarbamate
  参考文献：
  名称：

  Design, synthesis and evaluation of rivastigmine and curcumin hybrids as site-activated multitarget-directed ligands for Alzheimer’s disease therapy

  摘要：

  A series of novel 2-methoxy-phenyl dimethyl-carbamate derivatives were designed, synthesized and evaluated as site-activated MTDLs based on rivastigmine and curcumin. Most of them exhibited good to excellent AChE and BuChE inhibitory activities with sub-micromolar IC50 values. Among all the compounds, 6a demonstrated the most potent AChE inhibition with IC50 value of 0.097μM, which is about 20-fold than that of rivastigmine. In addition, the three selected compounds 5a, 6a and 6e demonstrated inhibitory activity against Aβ self-aggregation similar to cucurmin in TEM assay, which is obviously different from the weak activity of rivastigmine. Moreover, the hydrolysate of 6a (compound 7) also showed potent ABTS(+) scavenging and moderate copper ion chelating activity in vitro.

  DOI：

  10.1016/j.bmc.2014.07.009
• 作为产物：
  描述：

  异香兰素 、 二甲氨基甲酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以64.6%的产率得到5-formyl-2-methoxyphenyl dimethylcarbamate
  参考文献：
  名称：

  Design, synthesis and evaluation of rivastigmine and curcumin hybrids as site-activated multitarget-directed ligands for Alzheimer’s disease therapy

  摘要：

  A series of novel 2-methoxy-phenyl dimethyl-carbamate derivatives were designed, synthesized and evaluated as site-activated MTDLs based on rivastigmine and curcumin. Most of them exhibited good to excellent AChE and BuChE inhibitory activities with sub-micromolar IC50 values. Among all the compounds, 6a demonstrated the most potent AChE inhibition with IC50 value of 0.097μM, which is about 20-fold than that of rivastigmine. In addition, the three selected compounds 5a, 6a and 6e demonstrated inhibitory activity against Aβ self-aggregation similar to cucurmin in TEM assay, which is obviously different from the weak activity of rivastigmine. Moreover, the hydrolysate of 6a (compound 7) also showed potent ABTS(+) scavenging and moderate copper ion chelating activity in vitro.

  DOI：

  10.1016/j.bmc.2014.07.009

文献信息

• Discovery of Novel Pyrazolopyrimidinone Derivatives as Phosphodiesterase 9A Inhibitors Capable of Inhibiting Butyrylcholinesterase for Treatment of Alzheimer’s Disease
  作者：Yan-Fa Yu、Ya-Dan Huang、Chen Zhang、Xu-Nian Wu、Qian Zhou、Deyan Wu、Yinuo Wu、Hai-Bin Luo

  DOI：10.1021/acschemneuro.7b00268

  日期：2017.11.15

  gmine hybrids were designed, synthesized, and evaluated in vitro. Most compounds exhibited remarkable inhibitory activities against both PDE9A and BuChE. Compounds 6c and 6f showed the best IC50 values against PDE9A (6c, 14 nM; 6f, 17 nM) together with the considerable inhibition against BuChE (IC50, 6c, 3.3 μM; 6f, 0.97 μM). Their inhibitory potencies against BuChE were even higher than the anti-AD

  同时靶向不同因素以控制阿尔茨海默病（AD）复杂发病机理的多靶标配体（MTDL）的发现已成为近年来的重要研究领域。磷酸二酯酶9A（PDE9A）和丁酰胆碱酯酶（BuChE）抑制剂均可参与AD的不同过程，以减轻神经元损伤并改善认知障碍。然而，尚未报道对同时抑制PDE9A和BuChE的MTDLs的研究。在这项研究中，一系列新颖的吡唑并嘧啶，利凡斯的明杂种的设计，合成，并评价在体外。大多数化合物对PDE9A和BuChE均显示出显着的抑制活性。化合物6c和6f显示出最好的IC 50对PDE9A的值（图6c，14纳米; 1207米，17纳米）连同对所述的BuChE抑制相当（IC 50，图6c，3.3μM; 1207米，0.97μM）。它们对BuChE的抑制作用甚至比抗AD药物rivastigmine还要高。值得一提的是，两者对BuChE的选择性都比乙酰胆碱酯酶（AChE）中等。分子对接研究揭示了它们的结
• AMINOALKYLPHENOL DERIVATIVES AND RELATED COMPOUNDS
  申请人：AVENTIS PHARMACEUTICALS INC.

  公开号：EP1032559A1

  公开（公告）日：2000-09-06
• EP1032559A4
  申请人：——

  公开号：EP1032559A4

  公开（公告）日：2005-05-25
• US6479495B1
  申请人：——

  公开号：US6479495B1

  公开（公告）日：2002-11-12
• [EN] AMINOALKYLPHENOL DERIVATIVES AND RELATED COMPOUNDS<br/>[FR] DERIVES D'AMINO-ALKYLPHENOLS ET COMPOSES ASSOCIES
  申请人：AVENTIS PHARMACEUTICALS INC.

  公开号：WO1999016746A1

  公开（公告）日：1999-04-08

  (EN) Novel aminoalkylphenols, intermediates and processes for the preparation thereof, and methods of relieving memory dysfunction utilizing the aminoalkylphenols or compositions thereof are disclosed.(FR) L'invention concerne de nouveaux amino-alkylphénols, produits intermédiaires, et procédés de préparation de ceux-ci, ainsi que des méthodes destinées à soulager les troubles de la mémoire, grâce à une utilisation desdits amino-alkylphénols ou des compositions de ceux-ci.