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Molecules 2013, 18(3), 3595-3614; doi:10.3390/molecules18033595

Synthesis and Characterization of Celecoxib Derivatives as Possible Anti-Inflammatory, Analgesic, Antioxidant, Anticancer and Anti-HCV Agents

1
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Marmara University, Haydarpaşa, 34668 İstanbul, Turkey
2
Department of Pharmacology, Faculty of Pharmacy, Inonu University, 44280 Malatya, Turkey
3
Department of Biochemistry, Faculty of Pharmacy, Marmara University, Haydarpaşa, 34668 İstanbul, Turkey
4
Department of Biochemistry, Faculty of Pharmacy, Cumhuriyet University, 58140 Sivas, Turkey
5
Department of Biochemistry and Molecular Biology, UMDNJ-New Jersey Medical School, 185 South Orange Avenue, Newark, NJ 07103, USA
6
Department of Pharmaceutical Sciences, College of Pharmacy and Allied Health Professions, St. John’s University, Jamaica, NY 11439, USA
This work was partly presented at the ISTE-C, P.988-993, İstanbul, Turkey, 7–9 December 2012.
*
Author to whom correspondence should be addressed.
Received: 31 January 2013 / Revised: 12 February 2013 / Accepted: 10 March 2013 / Published: 21 March 2013
(This article belongs to the Special Issue Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry)
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Abstract

A series of novel N-(3-substituted aryl/alkyl-4-oxo-1,3-thiazolidin-2-ylidene)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamides 2ae were synthesized by the addition of ethyl a-bromoacetate and anhydrous sodium acetate in dry ethanol to N-(substituted aryl/alkylcarbamothioyl)-4-[5-(4-methylphenyl)-3-(trifluoro-methyl)-1H-pyrazol-1-yl]benzene sulfonamides 1ae, which were synthesized by the reaction of alkyl/aryl isothiocyanates with celecoxib. The structures of the isolated products were determined by spectral methods and their anti-inflammatory, analgesic, antioxidant, anticancer and anti-HCV NS5B RNA-dependent RNA polymerase (RdRp) activities evaluated. The compounds were also tested for gastric toxicity and selected compound 1a was screened for its anticancer activity against 60 human tumor cell lines. These investigations revealed that compound 1a exhibited anti-inflammatory and analgesic activities and further did not cause tissue damage in liver, kidney, colon and brain compared to untreated controls or celecoxib. Compounds 1c and 1d displayed modest inhibition of HCV NS5B RdRp activity. In conclusion, N-(ethylcarbamothioyl)-4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (1a) may have the potential to be developed into a therapeutic agent.
Keywords: anti-inflammatory; anticancer; celecoxib; hepatitis C NS5B; sulfonylthiourea anti-inflammatory; anticancer; celecoxib; hepatitis C NS5B; sulfonylthiourea
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Küçükgüzel, Ş.G.; Coşkun, İ.; Aydın, S.; Aktay, G.; Gürsoy, Ş.; Çevik, Ö.; Özakpınar, Ö.B.; Özsavcı, D.; Şener, A.; Kaushik-Basu, N.; Basu, A.; Talele, T.T. Synthesis and Characterization of Celecoxib Derivatives as Possible Anti-Inflammatory, Analgesic, Antioxidant, Anticancer and Anti-HCV Agents. Molecules 2013, 18, 3595-3614.

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