Synthesis and biological activity on IBD virus of diverse heterocyclic systems derived from 2-cyano-N'-((2-oxo-1,2-dihydroquinolin-3-yl)methylene)acetohydrazide

Abstract

A 2-cyano-N'-((2-oxo-1,2-dihydroquinolin-3-yl)methylene)ethanohydrazide (3) was synthesized in 87% yield via condensation of 3-formyl-2-oxoquinoline (1) with 2-cyanoethanohydrazide (2). The titled compound was then treated with some electrophilic reagents to construct some novel quinoline-based heterocyclic systems, for example, pyrazole, thiazoline, pyridine, pyrimidine, chromene, and thiophene derivatives. The behavior of the titled compound toward hydrazine and phenylhydrazine was examined. Seven substances were screened for their in vitro antiviral activity against infectious bursal disease virus (IBDV) in specific pathogen-free (SPF) chicken embryos and evaluation of immune-boosting properties of these substances in SPF chicks. The antiviral results disclosed that compounds 5a and 17 exhibited the most potency as compared to the reference drug, ribavirin. Therefore, they are considered as promising antiviral additives in vaccine production of IBVD vaccine to increase the immune stimulant.

Graphical Abstract

Keywords:

• Chromene
• IBD virus
• pyrimidine
• quinoline
• thiophene

Disclosure statement

The authors declare no conflict of interest.