rac- and meso-Cyclohexanoids: Their α-, β-glycosidases, antibacterial, antifungal activities, and molecular docking studies
| Autor: | Emel Karakılıç, Şule Baran, Hatice Öğütcü, Arif Baran, Atilla Akdemir |
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| Přispěvatelé: | Ziraat Fakültesi, Hatice Öğütçü / 0000-0001-7100-9318, AKDEMİR, ATİLLA |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Antifungal
Antifungal Agents Molecular model medicine.drug_class Saccharomyces cerevisiae Pharmaceutical Science Epoxide Microbial Sensitivity Tests Gram-Positive Bacteria 01 natural sciences chemistry.chemical_compound Hydrolysis Structure-Activity Relationship Cyclohexanes Furan Drug Discovery Candida albicans Gram-Negative Bacteria inhibitors medicine Their alpha- beta-glycosidases antibacterial antifungal activities and molecular docking studies- ARCHIV DER PHARMAZIE 2020 [Karakilic E. Baran S. Ogutcu H. AKDEMİR A. Baran A. -rac- and meso-Cyclohexanoids] Glycoside Hydrolase Inhibitors antimicrobial activity biology Molecular Structure 010405 organic chemistry antifungal activity Stereoisomerism alpha-Glucosidases assay biology.organism_classification Combinatorial chemistry 0104 chemical sciences Anti-Bacterial Agents Molecular Docking Simulation 010404 medicinal & biomolecular chemistry chemistry Methanol |
| Popis: | 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 alpha- and beta-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 alpha-glucosidase molecular modeling studies were performed for all rac- and meso-compounds 7, 8, 10, 17, 18, and 19. Türkiye Bilimsel Ve Teknolojik Araştırma Kurumu ( Tübitak ) |
| Databáze: | OpenAIRE |
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