Synthesis and Bioactivity of Novel Tri-Heterocyclic Molecules: {4-[3-({[5-(Substituted)-1,3,4-Oxadiazol-2-Yl] SulfanyljMethyl) Benzoyl] -1 -Piperazinyl} (2-Furyl)Methanones (AOICS) - Lupine Publishers
In the presented investigation, some novel tri-heterocyclic
benzamides, 8a-g, were synthesized in several steps. First, the
electrophilic benzamide,
{4-[3-(chloromethyl)benzoyl]-1-piperazinyl}(2-furyl) methanone (3), was
synthesized by the reaction of 2- Furoyl-1-piperazine (1) and
3-chloromethylbenzoyl chloride (2). In second series of steps, different
carboxylic acids, 4a-g, were refluxed with ethanol and conc. sulfuric
acid to form esters, 5a-g. These esters were further refluxed with N2H4.H2O
in methanol solution to acquire acid respective hydrazides, 6a-g. These
hydrazides were cyclized by refluxing with KOH, ethanol and CS2
into corresponding 1,3,4-oxadiazoles, 7a-g. In the final step, the
electrophile, 3, was coupled with synthesized 1,3,4-oxadiazoles, 7a-g,
in acetonitrile and potassium carbonate to acquire the targeted
tri-heterocyclic molecules, 8a-g. The structural characterization of
these novel compounds 8a-g was done by IR, 1H-NMR, 13C-NMR
and EI-MS spectral data. These synthesized molecules were subjected to
antibacterial and enzyme inhibitory and cytotoxicity evaluation. Among
the series, 8b exhibit good enzyme inhibition whereas 8c exhibited good
antibacterial and antifungal potential against B. subtilis, E. coli and A. flavus
strains, respectively. Most of the molecules possessed moderate
cytotoxicity and hence these can be utilized as possible therapeutic
agents.
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