Efficient synthesis, molecular docking and ADMET studies of new 5-substituted tetrazole derivatives

•A new series of 5-substituted tetrazole derivatives were synthesized.•This protocol has the advantages of good yields, green reaction conditions, broad functional group tolerance, excellent atom economy, simple operation, and the use of inexpensive and commercially available starting material.•Dock...

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Bibliographic Details
Published in:Journal of molecular structure 2023-04, Vol.1277, p.134867, Article 134867
Main Authors: Sadeghi, Zahra, Abolhasani, Hoda, Mirjafary, Zohreh, Najafi, Gholamreza, Heidari, Fatameh
Format: Article
Language:English
Subjects:
[2+‏3] Cycloaddition
ADMET study
Molecular docking
Sulfonamides
Tetrazole
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Summary:•A new series of 5-substituted tetrazole derivatives were synthesized.•This protocol has the advantages of good yields, green reaction conditions, broad functional group tolerance, excellent atom economy, simple operation, and the use of inexpensive and commercially available starting material.•Docking and ADMET studies reveal that compound 5e has the highest docking score for 1G3U, 1QSG, and 5F19, and having a higher LD50 for those three targets’ control molecules. In the present study, novel 5-substituted tetrazole derivatives bearing the sulfonamide group were synthesized using an azide-nitrile cycloaddition reaction. The easy availability of the inexpensive starting materials, avoiding isolation and handling of hazardous organic azide, and mild reaction conditions make this synthetic protocol a valuable tool for the synthesis of functionalized tetrazole derivatives. All reactions proceeded smoothly to achieve the corresponding 5-substituted tetrazole derivatives 5a-f in moderate to good yields (32-85%) using ZnBr2 as a catalyst and green solvent system H2O/2-propanol. The structure of all products was confirmed by FT-IR, 1HNMR, and 13CNMR analysis. Furthermore, we used molecular docking and ADMET studies to investigate the possible drug-likeness of the synthesized molecules 5a-f, revealing that some molecules are the most promising drug-like molecules out of the seven synthesized molecules. Antifungal activity of the compound 5c against standard strains of pathogenic fungi was also investigated in the final section of study. [Display omitted]
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2022.134867