Hantzsch-like three-component synthesis of bis(1,4-dihydropyridines) and bis(fused-1,4-dihydropyridines) linked to piperazine core via 2-phenoxyethanone linkage: Novel hybrid molecules

Abstract

The molecular hybridization of various compounds with known pharmacological activity is a particularly popular approach for the development of potential drugs with improved pharmacokinetic profiles. In this respect, a novel series of bis(1,4-dihydropyridine-3,5-dicarbonitrile), bis(decahydroacridine), bis(tetrahydrodipyrazolo[3,4-b:4′,3′-e]pyridin), and bis(tetrahydropyrimido[4,5-b]quinoline-2,4,6-trione) derivatives linked to piperazine core via phenoxyethanone linkages were prepared via Hantzsch like reaction of the ((piperazine-1,4-diylbis(2-oxoethane-2,1-diyl))bis(oxy))dibenzaldehydes, with the appropriate active methylene containing reagents. Attempted synthesis of the target products via bis-alkylation of the appropriate phenol with 1,1′-(piperazine-1,4-diyl)bis(2-chloroethan-1-one) in different basic conditions were unsuccessful.

Graphical Abstract

Keywords:

• bis(decahydroacridine)
• bis(1,4-dihydropyridine-3,5-dicarbonitrile)
• bis(tetrahydrodipyrazolo[3,4-b:4′,3′-e]pyridine)
• bis(tetrahydropyrimido[4,5-b]quinolone
• piperazine core