RESUMO
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 ß-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.
Assuntos
Antibacterianos/farmacologia , Antifúngicos/farmacologia , Cicloexanos/farmacologia , Inibidores de Glicosídeo Hidrolases/farmacologia , Simulação de Acoplamento Molecular , alfa-Glucosidases/metabolismo , Antibacterianos/síntese química , Antibacterianos/química , Antifúngicos/síntese química , Antifúngicos/química , Candida albicans/efeitos dos fármacos , Cicloexanos/síntese química , Cicloexanos/química , Inibidores de Glicosídeo Hidrolases/síntese química , Inibidores de Glicosídeo Hidrolases/química , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Saccharomyces cerevisiae/enzimologia , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
Stereoselective and efficient synthesis of hydroxymethyl-substituted rac-quercitols (13-15) was achieved, starting from cis-furan (Kobayashi, 2008) with photooxygenation reaction, which is readily available by the reduction of cis-phtalic anhydride. α- and ß-Glucosidase enzyme activity of the target molecules was evaluated and good inhibitor activity was seen. One- and two-dimensional NMR spectroscopy, IR spectroscopy and X-ray crystallography were utilized in the structure characterization of products.
Assuntos
Glucosidases/antagonistas & inibidores , Inibidores de Glicosídeo Hidrolases/farmacologia , Inositol/análogos & derivados , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Glucosidases/metabolismo , Inibidores de Glicosídeo Hidrolases/síntese química , Inibidores de Glicosídeo Hidrolases/química , Humanos , Inositol/síntese química , Inositol/química , Inositol/farmacologia , Modelos Moleculares , Estrutura Molecular , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
In order to assess the relationship between the oppiid mite species (Acari, Oribatida) collected from Turkey, traditional and geometric morphometric methods were used. We have taken photographs of 128 specimens belonging to 11 species from six subfamilies of Oppiidae. These photographs were digitized and 17 interval measurements were taken for traditional morphometric analysis, and 20 landmarks were recognized on the ventral surface of each specimen for geometric morphometric analysis. The effectiveness to separate taxa was compared between the two morphometric analyses. In both dendrograms Oppia nitens formed a single cluster, Oxyoppia ilicaensis was singled out from the remaining nine species, which were clustered together. Two species, Lauroppia fallax and Rhinoppia obsoleta, clustered together implying a very close relationship.