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
Volume 1 - Issue 2
Muhammad Athar Abbasi1*, Aziz-ur-Rehman1, Sabahat Zahra Siddiqui1, Syed Adnan Ali Shah2,3 and Muhammad
Shahid4
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- 1Department of Chemistry, Government College University, Pakistan
- 2Faculty of Pharmacy, Selangor Darul Ehsan, Malaysia
- 3Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Malaysia
- 4Department of Biochemistry, University of Agriculture, Pakistan
*Corresponding author:
Muhammad Athar Abbasi, aDepartment of Chemistry, Government College University, Lahore-54000, Pakistan
Received: January 16, 2018; Published: February 01, 2018
DOI: 10.32474/AOICS.2018.01.000108
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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.
Keywords: Tri-Heterocyclic; 1H-NMR; 13C-NMR; EI-MS; Hemolytic Activity; Enzyme Inhibition; Antibacterial; Antifungal activity.
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