Synthesis and antimicrobial, acetylcholinesterase and butyrylcholinesterase inhibitory activities of novel ester and hydrazide derivatives of 3 (2H)-pyridazinone

Abstract

In the current study, some novel ethyl 6- [(substituted-phenylpiperazine]-3(2H)-pyridazinone-2-yl propionate III and 6-[(substituted-phenylpiperazine]-3(2H)-pyridazinone-2-yl propionohydrazide IV derivatives were synthesized as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors. The structures of these new pyridazinone derivatives were confirmed by their IR, 1H-NMR spectra and elementary analysis. 6-Substituted-3(2H)-pyridazinone-2-yl propionate IIIa-e derivatives showed significant inhibitory activity against AChE and BChE. 6-[4-(3-Trifluoromethylphenyl)piperazine]-3(2H)-pyridazinone-2-yl propionate IIIe has been found to be the most active compound in terms of inhibition of either AChE or BChE. Compound IIIe exhibited inhibitory activity close to that of galantamine (CAS 357-70-0) and did not show any selectivity between the two enzymes. Also the antimicrobial activities of III and IV derivatives have been evaluated. All III and IV derivatives exhibited poor antibacterial activities but moderate antifungal activities.

Synthesis of novel 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(substituted/-nonsubstituted benzal)hydrazone derivatives and acetylcholinesterase and butyrylcholinesterase inhibitory activities in vitro

“…The physicaland spectralp ropertiesof 3-chloro-6-substitutedpyridazine I werei naccordancewiththe literature [13,14].Thereforewecarried out the next stepsof the reaction without anyfurtheranalysis. [15 -20].Ten of the 6-substituted-3(2 H )-pyridazinone-2-acetyl-2-(substituted/nonsubstituted benzal)hydrazone V derivativesw erereported for the first time in thiss tudy.Compounds Va, Vh and Vj weresynthesized in our previous study [20].…”

Diverse chemical and biological potentials of various pyridazine and pyridazinone derivatives

“…Compound IIIe exhibited inhibitory activity close to that of galantamine (CAS 357-70-0) and did not show any selectivity between the two enzymes. All derivatives exhibited poor antibacterial activities but moderate antifungal activities (Ozçelik at al., 2010). The SAR and modeling of a series of 5-substituted-Naryl pyridazinone based p38alpha inhibitors are described.…”

Efficient Synthesis, Antimicrobial, Antioxidant Assessments and Geometric Optimization Calculations of Azoles‐ Incorporating Quinoline Moiety

“…Hydrazides have been described as useful key compound to synthesize various heterocyclic compounds . Hydrazides are reported to have different and rich biological properties . Hydrazones are used in electrophotography, due to their relatively simple synthesis, low molecular weight, and aperture‐conveying properties .…”