5-ARYL-7,8,9,10-TETRAHYDRO-5H-TETRAZOLO[1,5-а]THIOPYRANO[3,2-d]PYRIMIDINE 6,6-DIOXIDES – A NEW HETEROCYCLIC ENSEMBLE via MCR APPROACH
DOI:
https://doi.org/10.15421/jchemtech.v31i2.126304Keywords:
azaheterocycles, sulfones, 5-aminotetrazole, microwave irradiation, multicomponent reactions (MCR)Abstract
Tetrazoles are found broad applications in numerous fields such as in medicine, biochemistry, pharmacology, and in industry. Considering our continued interest in new azaheterocycles based on β-ketosulfones in this work a three-component heterocyclization of dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide, 1H-tetrazol-5-amine, and aromatic aldehydes under microwave irradiation was studied. Regardless of the reaction conditions, 5-aryl-7,8,9,10-tetrahydro-5H-tetrazolo[1,5-a]thiopyrano[3,2-d]pyrimidine 6,6-dioxides were isolated as sole reaction products in good to excellent yields. To the best of our knowledge mentioned azaheterocycles are novel and previously not reported heterocyclic ensemble. Proposed structures were confirmed by spectral methods. Considering druglikeness we can conclude that compounds match parameters for Lipinski, Ghose, Veber, Egan and Muegge rules, and also correspond to the V class of acute toxicity. In silico screening of the biological profile of new derivatives showed adequate ADMET properties along with high (60 % and more) probability levels of activity against such pathogens/diseases as Candida albicans, Alphis gossypii, Tripomastigote Chagas, Tcruzi amastigota, Tcruzi epimastigota etc.
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