N-phenethyl-2-(1H-1,2,3-triazol-1-yl)acetamide derivatives: Synthesis, crystal structure and molecular docking studies against SARS-CoV-2

被引：0

作者：

Cedillo-Cruz, Alberto ^{[1
,2
]}

Villalobos-Lopez, Diana Cecilia ^{[3
]}

Cruz, Abraham Kuri ^{[4
]}

Aguilar, Maria Isabel ^{[3
]}

Lara-Almazan, Nancy ^{[5
]}

Martinez-Otero, Diego ^{[1
]}

Cuevas-Yanez, Erick ^{[1
,2
]}

机构：

[1] Univ Autonoma Estado Mexico, Ctr Conjunto Invest Quim Sustentable UAEM UNAM, Carretera Toluca Atlacomulco Km 14-5, Toluca 50200, Estado De Mexic, Mexico

[2] Univ Autonoma Estado Mexico, Fac Quim, Paseo Colon Esq Paseo Tollocan, Toluca 50120, Estado De Mexic, Mexico

[3] Univ Nacl Autonoma Mexico, Fac Quim, Dept Farm, Cd Univ, Ciudad De Mexico 04510, Mexico

[4] Natl Inst Stand & Technol NIST, Chem Sci Div, 100 Bur Dr, Gaithersburg, MD 20899 USA

[5] Inst Nacl Invest Nucl, Dept Forense Nucl & Quim Analit, Ocoyoacac 52750, Estado De Mexic, Mexico

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2025年 / 1321卷

关键词：

SARS-CoV-2; inhibitors; Molecular docking; Triazole derivatives; Click chemistry; Crystal structure; FRAGMENTATION; INHIBITION; TRIAZOLES; PROTEASE;

D O I：

10.1016/j.molstruc.2024.140167

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Novel N-phenethyl-2-(1H-1,2,3-triazol-1-yl)acetamide derivatives were synthesized via Copper(I)-catalyzed 1,3dipolar azide-alkyne cycloaddition, commonly known as CuAAC. These triazoles were then characterized using Nuclear Magnetic Resonance (NMR), Fourier Transform Infrared Spectroscopy (FTIR), and Mass Spectrometry (MS). The crystal structures of ten compounds were elucidated through single-crystal X-ray diffraction (SCXRD). Computational calculations, based on Density Functional Theory (DFT), were employed to optimize the molecular structures. The energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) were also determined. Additionally, molecular docking studies revealed the binding interactions of the most potent triazole with the active sites of key molecular targets. The findings indicated that the newly synthesized triazoles exhibit promising inhibitory activity against SARS-CoV-2 proteases 3-chymotrypsin-like protease (3CL(pro)), papain-like protease (PLpro), and helicase, outperforming the cocrystallized ligand.

引用

页数：20

共 57 条

[1] 1,2,3-Triazole-Benzofused Molecular Conjugates as Potential Antiviral Agents against SARS-CoV-2 Virus Variants [J].