Antibacterial Activity, Quantitative Structure–Activity Relationship and Diastereoselective Synthesis of Isoxazolidine Derivatives Via 1,3‐Dipolar Cycloaddition of d‐glucose Derived Nitrone with Olefin

Abstract

The diastereoselectivity of the intermolecular 1,3-dipolar cycloaddition reaction of d-glucose-derived nitrones with both cyclic and acyclic dipolarophiles were studied. The reaction of nitrone with acyclic dipolarophiles resulted in the formation of the endo adduct exclusively whereas with cyclic dipolarophiles endo adduct was obtained as the major product. Antibacterial activity was evaluated for these eighteen isoxazolidine derivatives against Staphylococcus aureus NCIM5021, Escherichia coli NCIM 2931 and Pseudomonas aeruginosa NCIM 5029 by twofold dilution technique using resazurin as the indicator dye. Quantitative structureactivity relationships were developed with fourteen and the model was validated with four data. Electronic and spatial descriptors were the major contributors in all the three quantitative structureactivity relationship equations and the statistical parameters r(2), r(2)(adj) , F-ratio and q(2) were found to be satisfactory.

Activity of the novel fungicide SYP-Z048 against plant pathogens

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Unprecedented Synthesis of 4‐Ylidene (3 S)‐3‐hydroxy‐1‐aryl (alkyl)‐pyrrolidine‐2,5‐diones Based on 1,3‐Dipolar Cycloaddition of a Sugar‐derived Nitrone to N‐Substituted Maleimides

“…The Z ‐geometry of sugar nitrone 2 was established by a 2D NOESY experiment showing visible correlations between the azomethine proton and the benzyl protons (besides expected correlations between H‐1 and H‐2, H‐2 and the methoxy protons, H‐3 and H‐4, H‐3 and OMe) and by the appearance of the azomethine proton at 6.81 ppm. In the case of a E ‐geometry, literature data showed the azomethine proton appearing at 8.0‐8.5 ppm …”

An Updated Review on the Synthesis and Antibacterial Activity of Molecular Hybrids and Conjugates Bearing Imidazole Moiety

“…For several years, studies have been carried out to identify isoxazolidine derivatives with significant antibacterial properties [179][180][181][182]. In 2004, Rangappa and coworkers synthesised with high regioselectivity isoxazolidine/imidazole hybrids 291a-j and tested their antibacterial activities against S. aureus, E. coli, and B. subtilis by using streptomycin as a positive control [183].…”