Synthesis, characterization, in vitro antimicrobial, and anthelmintic evaluations of 2-(4-chloro-3-methylphenoxy)-N′-[{5′-(substituted aryl)-furan-2′-yl}-methylidene]-acetohydrazides

Abstract

In the present study, a novel series of 2-(4-chloro-3-methylphenoxy)-N′-[{5′-(substituted aryl)-furan-2′-yl}-methylidene]-acetohydrazides (4a–k) have been designed and synthesized with a new class of p-chloro-m-cresol Schiff bases, derived from the reaction of p-chloro-m-cresol 1, with ethylchloroacetate in anhydrous condition yielded 2-(4-chloro-3-methylphenoxy) acetate 2, which was treated with hydrazine hydrate to yield 2-(4-chloro-3-methylphenoxy) acetohydrazide 3, Further the resultant compound (3) was treated with different aromatic furfural aldehydes to yield Schiff bases (4a–k). All the synthesized compounds were confirmed to their spectral (IR, ¹H NMR, ¹³C NMR, Mass, and CHN analysis) data. The current research also involved for their in vitro antibacterial screening in respect of the zone of inhibition (mm), against Gram-positive bacterial strains, Staphylococcus aureus (ATCC 11633), Bacillus cereus (ATCC 11778), Enterococcus faecalis (ATCC 14506), and Staphylococcus epidermidis (ATCC 155) and Gram-negative bacteria, Escherichia coli (ATCC10536), Salmonella typhi (MTCC 733), Shigella dysenteriae (ATCC 13313), and Klebsiella pneumoniae (ATCC 10031). Among the tested compounds, the most effective compound 4k exhibited very promising antibacterial activity when tested against strains of S. epidermidis, K. pneumoniae. While other compounds displayed moderate to good antibacterial activity. The synthesized Schiff bases also showed significant anthelmintic activity against two species of earthworms (Pheretima posthuma and Perionyx excavates).