Synthesis, spectral analysis, in vitro microbiological evaluation and antioxidant properties of 2,4-diaryl-3-azabicyclo[3.3.1]nonane-9-one-O-[2,4,6-tritertiarybutyl-cyclohexa-2,5-dienon-4-yl] oximes as a new class of antimicrobial and antioxidant agents

Abstract

Aims

The aim of the present study was to synthesis of a new series of bicyclic oximes with cyclohexadienone nuclei namely 2,4-diaryl-3-azabicyclo[3.3.1]nonane-9-one-O-[2,4,6-tritertiarybutylcyclohexa-2,5-dienon-4-yl]oximes [9–12] and screening for their antimicrobial activities and antioxidant activities.

Methods

Compounds 9–12 were synthesized by the treatment of 2,4,6-tritertiarybutyl phenol with corresponding 2,4-diaryl-3-azabicyclo[3.3.1]nonane-9-one oximes in the presence of an oxidizing agent, MnO₂ under nitrogen atmosphere. The compounds were characterized by melting point, elemental analysis, FT-IR, MS, ¹H and ¹³C NMR spectroscopic data. All the synthesized title compounds were screened for their antimicrobial activities by disc diffusion method against clinically isolated bacterial strains, the title compounds were also screened for their antioxidant activities by dose dependence manner using their free radical scavenging properties.

Results

The fluoro substituted compound 12 is found to have excellent level of antioxidant, antibacterial and antifungal activities.

Conclusion

In conclusion, a close examination of antioxidant, antibacterial and antifungal activities of variously substituted Compounds 9–12, reveals that they exhibits very good activities with better structure-activity correlations. Thus in future, this kind of oxime derivatives may be used to generate better drugs with improved antioxidant, antibacterial and antifungal activities.