Sobiech Monika, Maciejewska Dorota, Luliński Piotr
Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02-097 Warsaw, Poland.
Polymers (Basel). 2022 Jul 4;14(13):2738. doi: 10.3390/polym14132738.
The paper describes the formation of six aromatic -(2-arylethyl)-2-methylprop-2-enamides with various substituents in benzene ring, viz., 4-F, 4-Cl, 2,4-Cl, 4-Br, 4-OMe, and 3,4-(OMe) from 2-arylethylamines and methacryloyl chloride in ethylene dichloride with high yields (46-94%). The structure of the compounds was confirmed by H NMR, C NMR, IR, and HR-MS. Those compounds were obtained to serve as functionalized templates for the fabrication of molecularly imprinted polymers followed by the hydrolysis of an amide linkage. In an exemplary experiment, the imprinted polymer was produced from N-(2-(4-bromophenyl)ethyl)-2-methylprop-2-enamide and divinylbenzene, acting as cross-linker. The hydrolysis of 2-(4-bromophenyl)ethyl residue proceeded and the characterization of material including SEM, EDS, C CP MAS NMR, and BET on various steps of preparation was carried out. The adsorption studies proved that there was a high affinity towards the target biomolecules tyramine and L-norepinephrine, with imprinting factors equal to 2.47 and 2.50, respectively, when compared to non-imprinted polymer synthesized from methacrylic acid and divinylbenzene only.
该论文描述了在二氯乙烷中，由2-芳基乙胺和甲基丙烯酰氯高产率（46 - 94%）地形成六种在苯环上带有各种取代基的芳香族-(2-芳基乙基)-2-甲基丙-2-烯酰胺，即4-F、4-Cl、2,4-Cl、4-Br、4-OMe和3,4-(OMe)。通过¹H NMR、¹³C NMR、IR和HR-MS对化合物的结构进行了确认。获得这些化合物是为了作为制备分子印迹聚合物的功能化模板，随后进行酰胺键的水解。在一个示例性实验中，印迹聚合物由N-(2-(4-溴苯基)乙基)-2-甲基丙-2-烯酰胺和作为交联剂的二乙烯基苯制备而成。进行了2-(4-溴苯基)乙基残基的水解，并在制备的各个步骤对包括SEM、EDS、¹³C CP MAS NMR和BET在内的材料进行了表征。吸附研究证明，与仅由甲基丙烯酸和二乙烯基苯合成的非印迹聚合物相比，对目标生物分子酪胺和L-去甲肾上腺素具有高亲和力，印迹因子分别等于2.47和2.50。
