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Int. J. Mol. Sci. 2014, 15(4), 5821-5837; doi:10.3390/ijms15045821
Article

Pharmacological Evaluation and Preparation of Nonsteroidal Anti-Inflammatory Drugs Containing an N-Acyl Hydrazone Subunit

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Received: 24 December 2013; in revised form: 14 February 2014 / Accepted: 18 March 2014 / Published: 4 April 2014
(This article belongs to the Section Molecular Recognition)
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Abstract: A series of anti-inflammatory derivatives containing an N-acyl hydrazone subunit (4ae) were synthesized and characterized. Docking studies were performed that suggest that compounds 4ae bind to cyclooxygenase (COX)-1 and COX-2 isoforms, but with higher affinity for COX-2. The compounds display similar anti-inflammatory activities in vivo, although compound 4c is the most effective compound for inhibiting rat paw edema, with a reduction in the extent of inflammation of 35.9% and 52.8% at 2 and 4 h, respectively. The anti-inflammatory activity of N-acyl hydrazone derivatives was inferior to their respective parent drugs, except for compound 4c after 5 h. Ulcerogenic studies revealed that compounds 4ae are less gastrotoxic than the respective parent drug. Compounds 4be demonstrated mucosal damage comparable to celecoxib. The in vivo analgesic activities of the compounds are higher than the respective parent drug for compounds 4ab and 4de. Compound 4a was more active than dipyrone in reducing acetic-acid-induced abdominal constrictions. Our results indicate that compounds 4ae are anti-inflammatory and analgesic compounds with reduced gastrotoxicity compared to their respective parent non-steroidal anti-inflammatory drugs.
Keywords: anti-inflammatory; analgesic; hydrazone; molecular hybridization; non-steroidal anti-inflammatory; NSAID; docking; molecular modeling; COX anti-inflammatory; analgesic; hydrazone; molecular hybridization; non-steroidal anti-inflammatory; NSAID; docking; molecular modeling; COX
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

de Melo, T.R.F.; Chelucci, R.C.; Pires, M.E.L.; Dutra, L.A.; Barbieri, K.P.; Bosquesi, P.L.; Trossini, G.H.G.; Chung, M.C.; dos Santos, J.L. Pharmacological Evaluation and Preparation of Nonsteroidal Anti-Inflammatory Drugs Containing an N-Acyl Hydrazone Subunit. Int. J. Mol. Sci. 2014, 15, 5821-5837.

AMA Style

de Melo TRF, Chelucci RC, Pires MEL, Dutra LA, Barbieri KP, Bosquesi PL, Trossini GHG, Chung MC, dos Santos JL. Pharmacological Evaluation and Preparation of Nonsteroidal Anti-Inflammatory Drugs Containing an N-Acyl Hydrazone Subunit. International Journal of Molecular Sciences. 2014; 15(4):5821-5837.

Chicago/Turabian Style

de Melo, Thais R.F.; Chelucci, Rafael C.; Pires, Maria E.L.; Dutra, Luiz A.; Barbieri, Karina P.; Bosquesi, Priscila L.; Trossini, Gustavo H.G.; Chung, Man C.; dos Santos, Jean L. 2014. "Pharmacological Evaluation and Preparation of Nonsteroidal Anti-Inflammatory Drugs Containing an N-Acyl Hydrazone Subunit." Int. J. Mol. Sci. 15, no. 4: 5821-5837.



Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert