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Carbohydr Res ; 485: 107812, 2019 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-31585251

RESUMO

Octyl ß-d-glucopyranoside (OBG), prepared from d-glucose and octan-1-ol employing MW method, was subjected to direct dimolar valeroylation in pyridine at room temperature (25 °C) with valeroyl chloride. This mainly furnished the corresponding 3,6-di-O-valeroate in 57% yield indicating the regioselectivity at C-6 and C-3 positions. For structural elucidation and to get newer glucopyranosides of potential antimicrobial 3,6-di-O-valeroate was further converted into four novel 2,4-di-O-acyl esters reasonably in good yields. Per-O-acetate and per-O-benzoate of OBG were also prepared for SAR study. PASS predication and in vitro antimicrobial studies established them as better antifungal agent than that of antibacterial. SAR study along with AdmetSAR and SwissADME suggested that incorporation of alkanoyl and aromatic ester groups on octyl glucopyranoside core increase antimicrobial potentiality in very low concentration (10 µgmL-1). Molecular docking revealed that novel 2,4-di-O-tosyl ester and 2,3,4,6-tetra-O-benzoyl ester may act as competitive inhibitors of lanosterol 14-alpha demethylase.


Assuntos
Anti-Infecciosos/síntese química , Anti-Infecciosos/farmacologia , Ésteres/química , Glucosídeos/síntese química , Glucosídeos/farmacologia , Anti-Infecciosos/química , Anti-Infecciosos/farmacocinética , Técnicas de Química Sintética , Glucosídeos/química , Glucosídeos/farmacocinética , Simulação de Acoplamento Molecular , Conformação Proteica , Esterol 14-Desmetilase/química , Esterol 14-Desmetilase/metabolismo , Relação Estrutura-Atividade
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