New bispyrazoline derivatives built around aliphatic chains: Synthesis, characterization and antimicrobial studies

Abstract

The bispyrazolines 3a-3h built around the alkyl chains of varying lengths have been synthesized from the cyclization reactions of bischalcones with phenyl hydrazine. The bischalcones 2a-2h were obtained from the Claisen-Schmidt reactions of acetophenone with various bisaldehydes 1a-1h. The intermediate bischalcones and final bisheterocyclic compounds have been characterized by means of IR, 1 H-NMR, 13 C-NMR, Mass (ESI) and elemental analysis. The antibacterial and antifungal activities of the synthesized compounds were also evaluated against the Klubsellia pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Bacillius subtilis and Aspergillius janus, Aspergillus niger and Pencillium glabrum, respectively. The antimicrobial behaviour of the bispyrazolines 3a-3h is found to be dependent on the length of internal spacer unit.

Synthesis and Biological Evaluation of Novel Bischalcone Derivatives as Carbonic Anhydrase Inhibitors

“…In the current study, we report the synthesis of bischalcone derivatives containing a methoxy group (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). We determined the inhibitory effects of these compounds on two a-CA isozymes, hCA I and hCA II.…”

“…Examples of these transformations are formed by joining two chalcone moieties together with different linkages such as bi‐aryl, di‐aryl ether, methylene, the carbon chains of varying lengths, Mannich base, etc. using Suzuki–Miyaura , Mannich , Ullmann , and Williamson reactions. Synthetic bischalcone bearing piperazine Mannich base linkage, which is ( E )‐1‐(4‐(4‐(5‐cinnamoyl‐2‐hydroxybenzyl)piperazin‐1‐yl)phenyl)‐3‐phenylprop‐2‐en‐1‐one ( IV ), showed inhibition of nitric oxide (NO) production in microglial cells and for in vitro anticancer activity.…”

Synthesis, Antimicrobial Studies, and Docking Simulations of New Bis(4,5‐dihydropyrazole) Derivatives

“…Chalcones are key synthones as their cyclocondensation reactions lead to the generation of many exotic heterocyclics, useful in the construction of novel antimicrobial products . Among these pyrazolines, five membered nitrogen‐containing heterocyclic compounds have attracted immense interest among the synthetic organic chemists owing to their broad biological spectrum in terms of antimicrobial, antitumor, antidepressant, MAO‐B inhibitors, anti‐amoebic, cyclooxygenase (COX‐2) inhibitors, immunosuppressive, and anti‐inflammatory agents . Many pyrazoline derivatives like antipyrene, morazone, famprofazone, and ramifonazone are employed as leading non‐steroidal anti‐inflammatory drugs .…”

Synthesis and Antimicrobial Evaluations of New 5‐aryl Linked Bispyrazolines

“…Bispyrazolines are the molecules which are formed by linking two pyrazoline moieties together through the carbon chain of varying lengths. In view of these observations and in continuation of our research program on the synthesis of five membered bisheterocyclics [24][25][26][27][28], we report herein the syntheses of new symmetrical bispyrazolines 4(a-g) built around the aliphatic linkers, which have been found to possess an interesting profile of antimicrobial properties.…”