O,S,Se-containing Biginelli products based on cyclic ß-ketosulfone and their postfunctionalization.
Beilstein J Org Chem
; 20: 2143-2151, 2024.
Article
en En
| MEDLINE
| ID: mdl-39224228
ABSTRACT
A one-pot three-component Biginelli synthesis of dihydropyrimidinones/thiones/selenones via acetic acid or solvent-free Yb(OTf)3-catalyzed tandem reaction of ß-ketosulfone (dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide), an appropriate urea, and arylaldehyde has been developed. The reaction proceeds with high chemo- and regioselectivity to give diverse DHPMs in reasonable yields up to 95%. Moreover, an SO2-containing analogue of anticancer drug-candidate enastron (SO2 vs C=O) was obtained by using the here reported method in gram scale. We also demonstrate the reactivity of the Biginelli product in various directions - synthesis of condensed thiazoles and tetrazoles. In silico assessment of ADMET parameters shows that most compounds meet the lead-likeness requirements. The biological profiles of new compounds demonstrate high probability levels of activity against the following pathogens/diseases Candida albicans, Alphis gossypii, Tripomastigote Chagas, Tcruzi amastigota, Tcruzi epimastigota, Leishmania amazonensis, and Dengue larvicida.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Beilstein J Org Chem
Año:
2024
Tipo del documento:
Article
País de afiliación:
Ucrania
Pais de publicación:
Alemania