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Molecules 2018, 23(8), 1859; https://doi.org/10.3390/molecules23081859

Design and Synthesis of New Benzophenone Derivatives with In Vivo Anti-Inflammatory Activity through Dual Inhibition of Edema and Neutrophil Recruitment

1
Chemistry Institute, Federal University of Alfenas, UNIFAL-MG, Alfenas 37130-001, Minas Gerais, Brazil
2
Department of Industrial Pharmacy, Federal University of Santa Maria, UFSM, Santa Maria 97105-900, Rio Grande do Sul, Brazil
3
Center of Biological Sciences and Health, Federal University of Western Bahia, UFOB, Barreiras 47808-021, Bahia, Brazil
4
Department of Chemistry, Federal University of Viçosa, UFV, Viçosa 36570-900, Minas Gerais, Brazil
*
Author to whom correspondence should be addressed.
Received: 7 November 2017 / Revised: 28 November 2017 / Accepted: 29 November 2017 / Published: 26 July 2018
(This article belongs to the Special Issue Anti-inflammatory Agents)
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Abstract

A series of novel benzophenone derivatives containing a thiazole heterocyclic nucleus were designed by molecular hybridization. Molecular docking studies have demonstrated the inhibitory potential of the designed compounds against cyclooxygenase (COX) isoenzymes. These compounds were synthesized, characterized, and evaluated for their anti-inflammatory properties by the croton oil-induced ear edema assay to examine their effect on both prostaglandin (PG) production and neutrophils recruitment. The thiazole derivatives displayed a potent effect in terms of reducing ear edema. The analysis suggested that the presence of 4-phenyl-2-hydrazinothiazole and the absence of C4′-OCH3 on the benzophenone derivative structure are strongly related to the inhibition of PG production. In addition, the derivatives 2e, 3a and 3c concomitantly inhibit PG production and neutrophil recruitment, which may be a mechanism of action better than of common NSAIDs due to their inability to inhibit the neutrophil recruitment. Thus, these compounds can be considered as potential lead compounds toward the development of new anti-inflammatory drugs with an innovating mechanism of action. View Full-Text
Keywords: hydrazinothiazole; tiosemicarbazone; molecular docking; structure activity relationship; ear edema hydrazinothiazole; tiosemicarbazone; molecular docking; structure activity relationship; ear edema
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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. (CC BY 4.0).

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Januario, J.P.; de Souza, T.B.; Lavorato, S.N.; Maiolini, T.C.S.; Domingos, O.S.; Baldim, J.L.; Folquitto, L.R.S.; Soares, M.G.; Chagas-Paula, D.A.; Dias, D.F.; dos Santos, M.H. Design and Synthesis of New Benzophenone Derivatives with In Vivo Anti-Inflammatory Activity through Dual Inhibition of Edema and Neutrophil Recruitment. Molecules 2018, 23, 1859.

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