Novel Hybrid Triazoline - Triazole Glycosides: Synthesis, Characterization, Antimicrobial Activity study via In Vitro, and In Silico Means

Alsaeedy M., AL-Adhreai A., Alrabie A., Al-Qadsy I., Khamees H. A., Alaizeri Z. A. M., ...More

CARBOHYDRATE RESEARCH, vol.532, 2023 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 532
  • Publication Date: 2023
  • Doi Number: 10.1016/j.carres.2023.108877
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, CAB Abstracts, Chemical Abstracts Core, Chimica, Compendex, EMBASE, Food Science & Technology Abstracts, Veterinary Science Database
  • Anadolu University Affiliated: No


Series of novel 1,2,3-triazole, and 1,2,3- triazoline glycosides (a-e) were efficiently synthesized starting from Darabinose in an effort to synthesize a new type of hybrid molecules containing sugar azide. The key step involved is the introduction of a new group, ethylene glycol, to the anomeric site and protection of the hydroxyl groups with acetic anhydride. Following that, the acetyl group is converted into ethylene glycol to tosylate. Compound Azido ethyl-O-beta-D-arabinofuranoside 4 was synthesized with good yield by treating the derivative 3 with sodium azide, which displaced the tosylate 3 and replaced it with the azide group. The new glycosides were synthesized via a 1,3-dipolar cycloaddition reaction between the intermediate compound 4 and several alkenes and alkynes. The triazole and triazoline compounds were characterized by FT-IR, 1H NMR, 13C NMR, LC/MS-IT-TOF spectral, and C & sdot;H.N. analysis. The antimicrobial screening was assayed using the disc diffusion technique revealed moderate to high potential inhibitory values against three test microorganisms compared to standard drugs. Their pharmacokinetics evaluation also showed promising drug-likeness and ADME properties. Furthermore, density functional theory (DFT) was utilized to obtain the molecular geometry of the title compounds utilizing B3LYP/6-311G++ (d, p), molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs) through the investigation of HOMO and LUMO orbitals, and energy gap value. A lower energy gap value denotes that electrons can be transported more easily, indicating that molecule (b) is more reactive than other compounds. Molecular docking analysis revealed that all the designed triazole and triazoline glycosides interacted strongly inside the active site of the enzyme (PDB ID: 2Q85). and exhibits high docking scores, higher than the standard drug. The range of docking scores is -7.99 kcal/mol compound (a) to -7.42 kcal/mol compound (e).