New Biphenyl‐Based Bispyrazolines: Synthesis, Antimicrobial, and Docking Studies

Abstract

In this study, a series of new bispyrazolines 8(a–f) have been prepared from the cyclization reactions of bischalcones 7(a–f) with phenyl hydrazine by refluxing under the alkaline alcoholic (KOH/EtOH) conditions. The O‐alkylation reactions of hydroxyl substituted chalcone 6 with different 1,ω‐dibromoalkanes in the presence of anhydrous potassium carbonate, tetrabutylammonium iodide, and dry acetone afforded the symmetrical new bischalcones 7(a–f) in good yields. Chalcone 6 was realized by using the Claisen–Schmidt reaction of m‐hydroxyacetophenone with bipheny‐4‐carboxaldehyde. The various spectroscopic parameters such as IR, 1H‐NMR, 13C‐NMR, and ESI‐MS have been thoroughly used for the structural interpretations of the newly prepared products. The in vitro antibacterial and antifungal activities of these compounds have been examined with the help of serial tube dilution method, and many of the tested products were found to be revealing the promising antimicrobial properties, which were evident from their minimum inhibitory concentration values. The molecular docking simulations of the synthesized substances have also been achieved to observe the structural association into the active site of the Escherichia coli FabH (PdB: 3IL9). Docking results of these compounds suggested that bispyrazoline 8b demonstrated the lowest binding energy that describes its higher stability into the pocket of E. coli. The excellent inhibitory activity of this bisheterocycle against E. coli FabH may be ascribed on the basis of hydrophobic and van der Waals interactions.

A Compendium of the Most Promising Synthesized Organic Compounds against Several Fusarium oxysporum Species: Synthesis, Antifungal Activity, and Perspectives

“…These bis heterocycles were obtained with yields between 70 to 80%. In vitro antifungal evaluation against F. oxysporum showed that these compounds have moderate activity, bis pyrazoline 62 , which exhibited the best activity (MIC between 16 µg/mL) and their corresponding intermediates bis chalcones [ 94 ].…”

Synthetic and antimicrobial studies of N‐substituted‐pyrazoline‐based new bisheterocycles

“…Owing to the significance of various heterocycles and in continuation of our research program in the synthesis of bioactive bisheterocyclic products, we reported here the synthesis of four series of novel bispyrazolines such as N ‐acetyl 3a‐d , N ‐carbothioamide 4a‐d , N ‐carboxamide 5a‐d , and N ‐phenyl 6a‐d using o/m/p ‐xylene and biphenyl aromatic chain linker. The interest behind the synthesis of these symmetrical novel bispyrazolines was to investigate the effect of N ‐substitution on pyrazoline ring upon their antimicrobial profile.…”

“…It would be highly advantageous here to develop the synthesis of rigid chain-linked new bischalcones by using the ordinary protocols and to investigate their chemical transformations in search of new symmetrical bisheterocycles. [38][39][40][41] Owing to the significance of various heterocycles and in continuation of our research program in the synthesis of bioactive bisheterocyclic products, [42][43][44][45][46] we reported here the synthesis of four series of novel bispyrazolines such as N-acetyl 3a-d, N-carbothioamide 4a-d, N-carboxamide 5a-d, and N-phenyl 6a-d using o/m/p-xylene and biphenyl aromatic chain linker. The interest behind the synthesis of these symmetrical novel bispyrazolines was to investigate the effect of Nsubstitution on pyrazoline ring upon their antimicrobial profile.…”