Synthesis and Bioactivity of Novel Tri-Heterocyclic Molecules: {4-[3-({[5-(Substituted)-1,3,4-Oxadiazol-2-Yl]Sulfanyl}Methyl) Benzoyl]-1-Piperazinyl}(2-Furyl)Methanones
Journal Title: Archives of Organic and Inorganic Chemical Sciences - Year 2018, Vol 1, Issue 2
Abstract
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.
Authors and Affiliations
Muhammad Athar Abbasi, Aziz ur Rehman, Sabahat Zahra Siddiqui, Syed Adnan Ali Shah
Keywords
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- EP ID EP576744
- DOI 10.32474/AOICS.2018.01.000108
- Views 81
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