Novel 1,2,3-Triazole-Based Benzothiazole Derivatives: Efficient Synthesis, DFT, Molecular Docking, and ADMET Studies

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 23; p. 8555
• Main Authors: Mirjafary, Zohreh, Mohammad Karbasi, Mahdieh, Hesamzadeh, Parsa, Shaker, Hamid Reza, Amiri, Asghar, Saeidian, Hamid
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01.12.2022; MDPI
• Subjects: 1,2,3-triazole; ADMET study; Anti-inflammatory agents; Antifungal Agents - pharmacology; Azide; Benzothiazole; Cancer; Carbon; click reaction; Cycloaddition; Cycloaddition Reaction; Density functional theory; Density functionals; DFT calculation; Diabetes; Drugs; Fungicides; Hydrogen; Inflammation; Molecular docking; Molecular Docking Simulation; Molecular Structure; Nitrogen; Proteins; Sodium; Solvents; Structure-Activity Relationship; Temperature effects; Triazoles; Triazoles - chemistry; Triazoles - pharmacology; Tuberculosis; DFT calculation; ADMET study; cycloaddition; molecular docking; click reaction; 1,2,3-triazole
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27238555

A new series of 1,2,3-triazole derivatives - based on benzothiazole were synthesized by the 1,3-dipolar cycloaddition reaction of S-propargyl mercaptobenzothiazole and α-halo ester/amide in moderate to good yields (47-75%). The structure of all products was characterized by H NMR, C NMR, and CHN elemental data. This protocol is easy and green and proceeds under mild and green reaction conditions with available starting materials. The structural and electronic analysis and H and C chemical shifts of the characterized structure of were also calculated by applying the B3LYP/6-31 + G(d, ) level of density functional theory (DFT) method. In the final section, all the synthesized compounds were evaluated for their anti-inflammatory activity by biochemical COX-2 inhibition, antifungal inhibition with CYP51, anti-tuberculosis target protein ENR, DPRE1, pks13, and Thymidylate kinase by molecular docking studies. The ADMET analysis of the molecules - revealed that and are the most-promising drug-like molecules out of the six synthesized molecules.