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

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

Ş. Güniz Küçükgüzel 1,* email, İnci Coşkun 1 email, Sevil Aydın 1 email, Göknur Aktay 2 email, Şule Gürsoy 2 email, Özge Çevik 3,4 email, Özlem Bingöl Özakpınar 3 email, Derya Özsavcı 3 email, Azize Şener 3 email, Neerja Kaushik-Basu 5 email, Amartya Basu 5 email and Tanaji T. Talele 6 email
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; in revised form: 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 2a–e 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 1a–e, 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

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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.

AMA Style

Küçükgüzel ŞG, Coşkun İ, Aydın S, Aktay G, Gürsoy Ş, Çevik Ö, Özakpınar ÖB, Özsavcı D, Şener A, Kaushik-Basu N, Basu A, Talele TT. Synthesis and Characterization of Celecoxib Derivatives as Possible Anti-Inflammatory, Analgesic, Antioxidant, Anticancer and Anti-HCV Agents. Molecules. 2013; 18(3):3595-3614.

Chicago/Turabian Style

Küçükgüzel, Ş. G.; Coşkun, İnci; Aydın, Sevil; Aktay, Göknur; Gürsoy, Şule; Çevik, Özge; Özakpınar, Özlem B.; Özsavcı, Derya; Şener, Azize; Kaushik-Basu, Neerja; Basu, Amartya; Talele, Tanaji T. 2013. "Synthesis and Characterization of Celecoxib Derivatives as Possible Anti-Inflammatory, Analgesic, Antioxidant, Anticancer and Anti-HCV Agents." Molecules 18, no. 3: 3595-3614.

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