Design, synthesis and biological evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones as a new class of antimicrobial agents

New series of 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one thiosemicarbazones (9–16) obtained from the corresponding 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones (1–8) upon cyclization with ethylbromoacetate in the presence of sodium acetate–acetic acid buffer afforded novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones (17–24). The synthesized compounds have been characterized by their elemental, analytical and spectral studies. Besides, the reported compounds were screened for their antibacterial and antifungal activities against a spectrum of microbial organisms. These studies proved that compounds 11/18/20/23 against Staphylococcus aureus, 19/20/24 against Salmonella typhi show maximum inhibition potency at low concentration (6.25 μg/ml) whereas 18/19 against Candida albicans and 19/20/21 against Rhizopus sp. showed beneficial antifungal activity at minimum concentration.

Graphical abstractA series of 2,4-diaryl-3-azabicyclo[3.3.1]nonane-9-one thiosemicarbazones (9–16) obtained from the corresponding 2,4-diaryl-3-azabicyclo[3.3.1]nonane-9-ones (ABN) (1–8) upon cyclization with ethylbromoacetate in the presence of sodium acetate–acetic acid buffer afforded 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene)hydrazono]-1,3-thiazolidin-4-ones (17–24). The reported compounds were explored for their antibacterial and antifungal activities against sensitive and resistant organisms.Figure optionsDownload full-size imageDownload as PowerPoint slide