Letters in Drug Design & Discovery

G. Perry
University of Texas
San Antonio, TX
USA
Email: lddd@benthamscience.org

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Synthesis and Biological Activity of Thiazole Dithiocarbamate Derivatives

Author(s): Nalan Gundogdu-Karaburun.

Graphical Abstract:


Abstract:

In this study, we aimed at the synthesis of new 2-((5-substituted-4-methylthiazol-2-yl)amino)-2-oxoethyl 4- substitutedpiperazine-1-carbodithioate derivatives and their antibacterial, antifungal, antioxidant and AChE inhibitory evaluations. A set of fifteen new compounds of 2-((5-substituted-4-methylthiazol-2-yl)amino)-2-oxoethyl 4-substitutedpiperazine- 1-carbodithioate derivatives were synthesised by reacting 2-chloro-N-(5-substituted-4-methylthiazole-2- yl)acetamide derivatives and sodium salts of appropriate N-substitutedpiperazine dithiocarbamic acids in acetone. The chemical structures of the compounds were elucidated by IR, 1H-NMR, 13C-NMR, MS spectral data and elemental analysis. The antibacterial and antifungal activities of the synthesised derivatives were tested against Gram (+), Gram (-) bacteria and yeasts such as Salmonella typhimurium, Staphylococcus epidermidis, Staphylococcus aureus, Escherichia coli, Candida albicans, Candida utilis, Candida tropicalis, Candida krusei and Candida glabrata using a microbroth dilution technique. Antimicrobial results showed that the compounds displayed minimum inhibitory concentrations in the range of 15.62-4000 µg/mL. Antioxidant activity of the synthesised derivatives was measured by scavenging activity against DPPH (2,2-Diphenyl-1-picrylhydrazyl) radical and qualitative ABTS (2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)) free radical scavenging assay and it was found that the compounds showed antioxidant activity. AChE inhibitory activity of the synthesised derivatives was tested against Donepezil for their ability to inhibit acetylcholinesterase (AChE) using a modification of Ellman’s spectrophotometric method. However, no significant inhibitory activity was observed.

Keywords: Thiazole, Dithiocarbamate, Antibacterial activity, Antifungal activity, Antioxidant activity, AChE inhibitory activity.

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Article Details

VOLUME: 11
ISSUE: 6
Year: 2014
Page: [814 - 823]
Pages: 10
DOI: 10.2174/1570180811999140515100911
Price: $58