基于 N-氨甲基吗啉的新型腙的合成及生物活性。
Synthesis and Biological Activity of New Hydrazones Based on N-Aminomorpholine.
机构信息
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Karaganda 100008, Kazakhstan.
Karaganda Industrial University, Temirtau 101400, Kazakhstan.
出版信息
Molecules. 2024 Jul 30;29(15):3606. doi: 10.3390/molecules29153606.
The data on the synthesis of N-aminomorpholine hydrazones are presented. It is shown that the interaction of N-aminomorpholine with functionally substituted benzaldehydes and 4-pyridinaldehyde in isopropyl alcohol leads to the formation of corresponding hydrazones. The structure of the synthesized compounds was studied by H and C NMR spectroscopy methods, including the COSY (H-H), HMQC (H-C) and HMBC (H-C) methodologies. The values of chemical shifts, multiplicity, and integral intensity of H and C signals in one-dimensional NMR spectra were determined. The COSY (H-H), HMQC (H-C), and HMBC (H-C) results revealed homo- and heteronuclear interactions, confirming the structure of the studied compounds. The antiviral, cytotoxic, and antimicrobial activity of some synthesized hydrazones were investigated. It is shown that 2-((morpholinoimino)methyl)benzoic acid has a pronounced viral inhibitory property, comparable in its activity to commercial drugs Tamiflu and Remantadine. A docking study was performed using the influenza virus protein models (1930 Swine H1 Hemagglutinin and Neuraminidase of 1918 H1N1 strain). The potential binding sites that are complementary with 2-((morpholinoimino)methyl)benzoic acid were found.
呈现了 N-氨甲基吗啉腙的合成数据。结果表明，N-氨甲基吗啉与功能取代的苯甲醛和 4-吡啶甲醛在异丙醇中的相互作用导致相应腙的形成。通过 H 和 C NMR 光谱方法，包括 COSY（H-H）、HMQC（H-C）和 HMBC（H-C）方法，研究了合成化合物的结构。确定了一维 NMR 光谱中 H 和 C 信号的化学位移、多重性和积分强度值。COSY（H-H）、HMQC（H-C）和 HMBC（H-C）的结果揭示了同核和异核相互作用，证实了所研究化合物的结构。研究了一些合成腙的抗病毒、细胞毒性和抗菌活性。结果表明，2-（（吗啉亚氨基）甲基）苯甲酸具有明显的抑制病毒活性，其活性可与商业药物达菲和金刚烷胺相媲美。使用流感病毒蛋白模型（1930 年猪 H1 血凝素和 1918 年 H1N1 株的神经氨酸酶）进行了对接研究。找到了与 2-（（吗啉亚氨基）甲基）苯甲酸互补的潜在结合位点。
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