rac‐ and meso‐Cyclohexanoids: Their α‐, β‐glycosidases, antibacterial, antifungal activities, and molecular docking studies

Abstract

An efficient and versatile synthesis method has been postulated for hydroxymethylated rac‐ and meso‐cyclohexanoid derivatives. The synthesis of these stereoisomers was achieved easily with traditional methods using hexahydroisobenzofuran 6, prepared from commercially available cis‐hydrophthalic anhydride. The study, involving diastereoselective epoxidation and cis‐hydroxylation, was conducted to obtain epoxy‐, cis‐, and trans‐diol‐furans 7, 8, and 9. After sulfamic acid‐catalyzed ring‐opening reaction of the epoxide and furan rings, rac‐ and meso‐tetraacetates 14, 15, and 16 were afforded. Hydrolysis of acetate groups with ammonia in absolute methanol yielded the desired tetrols rac‐17, meso‐18, and meso‐19. All structures, after purification by chromatographic methods and elucidation by spectral techniques, were screened against α‐ and β‐glucosidases. Compounds 7, 8, 10, 17, 18, and 19 were also evaluated for their antibacterial and antifungal activity against some selected synthesized compounds with varying degrees of inhibitory effects on the growth of different pathogenic microorganisms by the well‐diffusion method. In addition, Saccharomyces cerevisiae α‐glucosidase molecular modeling studies were performed for all rac‐ and meso‐compounds 7, 8, 10, 17, 18, and 19.

A polydentate ligand based on 2,2’-dipyridylamine unit linked benzo-15-crown-5; alkali and transition metal complexes; photoresponsive ligand; antimicrobial evaluation against pathogenic microorganisms

“…In the last stage, petri plates were incubated for 24 h at 37 °C on the incubator. On completion of the incubation period, the mean value obtained for the two wells were used to calculate the zone of growth inhibition of each sample The pathogenic bacterial cultures and yeast were tested for resistance to five antibiotics (Ampicillin, Nystatin, Kanamycin, Sulphamethoxazol, Amoxycillin) produced by Oxoid Lt., Basingstoke, UK [15,16].…”