RESUMEN

Thiazolidinones have been the subject of various research areas for their biological activities, thus they were promising scaffolds to develop new drug agents. A novel thiazolidine 4-one-based fluorescent chemosensor probes PS (thiazolidine) and BO (oxazolidine) were designed and synthesized. Both probes showed specific recognition against Cu2+ via a "turn-off" fluorescence response in ACN/H2O (v/v: 50/50) stock solution (10 mM, pH = 7.0) with a detection limit of (for BO: 1.9 nM and PS: 1.03 nM). Finally, the detection of chemosensory PS and BO showed positive potential for the determination of Cu2+ in real food samples, drinking water, and mung beans. The compounds were characterized by diferent chemical and spectroscopic methods. The proposed binding mode for PS and BO with Cu2+ was confirmed by DFT calculation, and also they elucidated by bioimaging studies against MCF-7 live cell lines. Additionally, the docking experiment was performed on XylE and hAChE targets.

RESUMEN

Utilization of fluorescent techniques in detection of various metal ions actively pursued allow ultrasensitive and selective detections of metal ions and prevent the adverse effect of cations such as aluminum (III) ions. In this study, two novel fluorescent chemosensors containing thiazole derivatives, ((E)-2-(4-hydroxy-3-(((2-hydroxyphenyl)imino)methyl)phenyl)-3-phenyl thiazolidin-4-one) AM1 and (2,3-bis(4-hydroxy-3-((E)-((2-hydroxyphenyl)imino) methyl) phenyl) thiazolidin-4-one) AM2, have been fabricated. The probes AM1 and AM2 were prepared using the condensation reaction between 2-hydroxy-5-(4-oxo-3-phenyl thiazolidin-2-yl) benzaldehyde and 2-aminophenol for the probe AM1 and 5,5'-(4-oxothiazolidine-2,3-diyl)bis(2-hydroxy benzaldehyde) and 2-aminophenol for the probe AM2. Afterwards, they were analyzed by various types of NMR and FT-IR spectroscopy, ESI-MS spectra, and elemental anayzer. As a second step, each fabricated chemosensor was able to use turn on fluorescence sensing for detecting of Al3+ ions in ACN/H2O (v/v = 50/50, 10.0 µM, pH = 7.0) solution. Clear complexes formed between the probe AM1 and Al3+ ions and also the probe AM2 and Al3+ ions was determined by not only 1H NMR titration study but also calculated by using the Job's plot. The limit of detection (LOD) value was found to be 0.11 µM (AM1) and 4.4 µM (AM2) for Al3+ ions. Likewise, cell imaging and in vitro cytotoxicity experiments of Al3+ ions in Human epithelium Lovo cells exhibited that prepared chemosensors had low cytotoxicity and blue fluorescence when they treated with of Al3+ ions in the cellular system.

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RESUMEN

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.

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In the present study, (3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran was submitted to photooxygenation and two isomeric hydroperoxides were successfully obtained. Without any further purification, reduction of the hydroperoxides with titanium tetraisopropoxide catalyzed by dimethyl sulfide gave two alcohol isomers in high yields. After acetylation of alcohol with Ac2O in pyridine, epoxidation reaction of formed monoacetates with m-CPBA, then chromatographed and followed by hydrolysis of the acetate groups with NH3 in CH3OH resulted in the formation of epoxy alcohol isomers respectively. These epoxy alcohol isomers were subjected to trans-dihydroxylation reaction with acid (H2SO4) in the presence of water to afford triols. Acetylation of the free hydroxyl groups produced benzofuran triacetates in high yields. Ring-opening reaction of furan triacetates with sulfamic acid catalyzed in the presence of acetic acid/acetic anhydrate and subsequently hydrolysis of the acetate groups with ammonia gave the targeted cyclohexane carbasugar-based pentols. All products were separated and purified by chromatographic and crystallographic methods. Structural analyses of all compounds were conducted by spectral techniques including NMR and X-ray analyses. The biological inhibition activity of the target compounds was tested against glycosidase enzymes, α- and ß-glucosidase.

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