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

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 ele...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-12, Vol.27 (23), p.8555
Main Authors: Mirjafary, Zohreh, Mohammad Karbasi, Mahdieh, Hesamzadeh, Parsa, Shaker, Hamid Reza, Amiri, Asghar, Saeidian, Hamid
Format: Article
Language:English
Subjects:
1,2,3-triazole
ADMET study
Anti-inflammatory agents
Antifungal 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
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27238555