Design, synthesis and in vitro antibacterial and antifungal activities of some novel spiro[azetidine-2,3′-indole]-2,4(1′H)-dione

Abstract

The present study deals with the synthesis of novel spiro[azetidine-2,3 0 -indole]-2 0 ,4(1 0 H)-dione derivative from the reactions of 3-(phenylimino)-1,3-dihydro-2H-indol-2-one derivatives with chloracetyl chloride in the presence of triethylamine (TEA). All the compounds were characterized using IR, 1 H-NMR, MS, and elemental analysis. They were screened for their antibacterial and antifungal activities. The bacterial strains used were Grampositive Staphylococcus aureus (MTCC-96) and Gramnegative Escherichia coli (MTCC-521) and Pseudomonas aeruginosa (MTCC-647). The antifungal screening was done on Candida albicans (MTCC-183) and Asperigillus niger (MTCC-343) fungal strains. Results revealed that, compounds (7a), (7b), (7c), (7d), and (7e) showed very good activity with MIC value of 6.25-12.5 lg/ml against three evaluated bacterial strains and the remaining compounds showed good to moderate activity comparable to standard drugs as antibacterial agents. Compounds (7c) and (7h) displayed equipotent antifungal activity in comparison to standard drugs. Amoxicillin, gentamycin, and streptomycin were used as standard drugs for antibacterial activity while fluconazole and itraconazole were used as standard drugs for antifungal activity. Structure-activity relationship study of the compounds showed that the presence of electron withdrawing group substitution at 5 0 and 7 0 positions of indoline ring and on ortho or para position of phenyl ring increases both antibacterial and antifungal activity of the compound. Henceforth, our findings will have a good impact on chemists and biochemists for further investigations in search of spiro-fused antimicrobial agents.

Antibacterial and β‐Lactamase Inhibitory Activity of Monocyclic β‐Lactams

“…It was also observed among all of the prepared compounds that o‐ and p ‐nitro‐substituted phenyl groups at position 1 of the monocyclic β‐lactam core increased the antibacterial activity against all tested bacterial strains. The potent compounds 155 and 156 thus inhibited S. aureus , E. coli , and P. aeruginosa with MIC values of 6.25 μg/mL, comparable with the well‐known penicillin amoxicillin and aminoglycoside gentamicin …”

“…The potent compounds 155 and 156 thus inhibited S. aureus, E. coli, and P. aeruginosa with MIC values of 6.25 μg/mL, comparable with the well-known penicillin amoxicillin and aminoglycoside gentamicin. 188…”

Monocyclic β-Lactams: New Structures for New Biological Activities

“…Compounds of this family were tested for antibacterial and antifungal activities with good results [23]. Spiro compound 12 with an indoline moiety showed good antifungal and antibacterial activity with MIC value of 6.25-12.5 μg/ml against three evaluated bacterial strains [24]. Structure-activity relationship study of these spiro-fused azetidinones showed that the presence of electron withdrawing group substitution on indoline ring and on N-phenyl ring increases both antibacterial and antifungal activity of the compound.…”

“…Some 3-amido-azetidinones were tested as inhibitors of cat K. They are characterized by a cyclic moiety on the C-3 side chain (24) which have proven to be crucial to achieve selectivity over other cathepsins [37]. The proposed mechanism of inhibition of cat K by 3,4-disubstituted azetidin-2-ones is depicted in Scheme 3 [38].…”

Green Synthesis of 1‐(1,2,4‐Triazol‐4‐yl)spiro[azetidine‐2,3′‐(3H)indole]‐2′,4′(1′H)‐diones as Potential Insecticidal Agents

“…The chemistry of spiro indoles in which an indole ring is joined to nitrogen containing heterocycles at C‐3 position through a spiro carbon atom has aroused great interest due to their physiological and biological activities . Amongst these spiro[azetidine‐indole] are known to possess antimicrobial activity . It was therefore, presumed that the title molecules incorporating indole, azetidinone, and triazole moieties would have enhanced biological properties.…”