Synthesis of Novel Isoxazolidine Derivatives and Their Antifungal and Antibacterial Properties

Abstract

The synthesis of some biologically interesting isoxazolidine derivatives has been accomplished by the cycloaddition reaction of C-(4-biphenyl)-N-(3-methylphenyl) nitrone and C-(4-biphenyl)-N-(3-chlorophenyl) nitrone to monosubstituted alkenes. The compounds were screened for their antibacterial and antifungal activities. Among the tested compounds 3a (ii), 3a (vii), 3a (viii), 3b (iv), 3b (vii), and 3b (viii) showed significant antifungal activity comparable with that of the standard drug Nystatin against Botrydiplodia theobromae.

Novel isoxazolidine analogues of homonucleosides and homonucleotides

“…12 Antiviral nucleotides were also discovered among phosphonylated isoxazolidines 2 13 and 3 14 as well as among their analogues having the 1,2,3-triazole linker 4. 16 On the other hand, it is worth mentioning that the biological activity of compounds containing the isoxazolidine ring is not restricted to anticancer and antiviral properties, since it was found that they also posses antimicrobial, 17,18 antifungal, 18e21 anti-inflammatory, 22,23 antioxidant 24,25 and insecticide activity, 26 among others. 14 High cytotoxicity toward several cancer cell lines was observed for isoxazolidine nucleosides of the general formula 5.…”

[(3R*,4R*,5R*)-2,3-Diphenylisoxazolidine-4,5-diyl]dimethanol

“…For general background to the preparation and use of compounds containing isoxazolidine rings, see: Agirbas et al (2007); Kelly et al (2009); Kumar et al (2003); Kwon et al (1995); Simonsen et al (1999). For graph-set analysis of hydrogen-bonded networks, see: Bernstein et al (1995).…”

“…Comment 1,3-Dipolar cycloaddition reaction of nitrones are the best templates for the construction of isoxazolidine rings (Simonsen et al, 1999). In recent years, useful anti-inflammatory (Kwon et al, 1995), immunosuppressive and antibacterial (Kumar et al, 2003) properties have been ascribed to molecules possessing such heterocyclic functionalities. In our previous work isoxazolidines obtained by 1,3-dipolar cycloaddition reactions have been found to have bioactivities to Enterococcus faecalis (ATCC 29212) and Staphylococcus aureus (ATCC 25923) (Agirbas et al, 2007).…”

Controlling Selectivity for Cycloadditions of Nitrones and Alkenes Tethered by Benzimidazoles: Combining Experiment and Theory

“…[1] Many variations in both the dipole and dipolarophile cycloaddition partners have been explored, as have inter- and intramolecular reaction manifolds, and the effects of various promoters. Although nitrone-alkene cycloaddition reactions have been utilized in the synthesis of many isoxaolidines, including those which form the cores of potential antifungal and antibacterial agents (e.g., 1 ), [2,3] some aspects of this chemistry would benefit from more detailed understanding. Herein we describe a combined experimental/theoretical study on the family of intramolecular nitrone-alkene cycloadditions shown in Scheme 1.…”