Objective: Arylidene-1, 3-oxazol-5-ones represent potential antibacterial agents. In the present work, a series of 4-substituted benzylidene-2- (phenoxymethyl) oxazol-5(4H)-ones were synthesized and screened for antibacterial activity against Gram-negative bacteria Escherichia coli. To explore plausible mechanisms, synthesized compounds were docked with DNA-Gyrase enzyme. Methods: All the reactants, phenoxy acetyl chloride, acetic anhydride, sodium acetate, substituted aromatic aldehydes, and glycine were triturated in a mortar by mechanical stirring. The antibacterial potentiality of the compounds was screened against E. coli using the disk diffusion method and the activity was recorded as a zone of inhibition. Results: Compound 2d, possessing 3, 4, 5-trimethoxy functionality on benzylidene ring exhibited the highest activity with 19 mm of the zone of inhibition which might be due to its higher interactions with DNA-Gyrase enzyme (ΔG-8.41 kcal/mol). Compounds 2a, 2b, and 2c exhibited moderate activity in the antimicrobial assay as well as in docking study indicating the positive contribution of substitution on benzylidene ring. Conclusion: A series of 4-substituted benzylidene-2-(phenoxymethyl) oxazol-5(4H)-ones were synthesized and evaluated for antibacterial activity. Compounds 2a, 2b, and 2c displayed moderate activity whereas 2d showed maximum zone of inhibition (19 mm). The good activity of these derivatives presumed to be due to the conformational flexibility of phenoxy methylene moiety which can be well accommodated in the target binding site.
A series of novel phenoxy acetyl carboxamides (4a-4g) were synthesized by amidation using phenoxy acetyl hydrazide and various acid chlorides (benzoyl, adamantly carbonyl cinnamoyl, 4-chloro benzoyl chlorides) or bases (piperidine, morpholine & substituted piperidinone) and evaluated for antioxidant and antinociceptive activities. The title compounds were purified by recrystallization using ethanol and characterized by spectral (FTIR, 1H NMR, and Mass) analysis. Compound 4a was effective in scavenging the DPPH radicals (57%) and nitric oxide (NO) radicals (52%) while compound 4e was able to significantly neutralize ABTS cation radicals (58%). However, the radical scavenging ability was lesser compared to the standard antioxidant agents. Among the tested compounds, 4f and 4g elicited good antinociceptive activity in the central and peripheral animal models (25 mg/kg body weight). Compounds 4b and 4f seem to open ATP-sensitive potassium channels (KATP channels), a possible mechanism for their peripheral effects. The carboxamides bind well with the monoglyceride lipase enzyme (MAGL) and established strong interactions at the active site.
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