Literature DB >> 27526659

New pyrazole derivative 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole: synthesis and assessment of some biological activities.

Lanussy Porfiro de Oliveira1, Daiany Priscilla Bueno da Silva1, Iziara Ferreira Florentino1, James Oluwagbamigbe Fajemiroye1, Thiago Sardinha de Oliveira2, Renato Ivan de Ávila Marcelino3, Francine Pazini4, Luciano Morais Lião5, Paulo César Ghedini2, Soraia Santana de Moura3, Marize Campos Valadares3, Verônica Vale de Carvalho5, Boniek Gontijo Vaz5, Ricardo Menegatti4, Elson Alves Costa1.   

Abstract

The molecular modification and synthesis of compounds is vital to discovering drugs with desirable pharmacological and toxicity profiles. In response to pyrazole compounds' antipyretic, analgesic, and anti-inflammatory effects, this study sought to evaluate the analgesic, anti-inflammatory, and vasorelaxant effects, as well as the mechanisms of action, of a new pyrazole derivative, 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole. During the acetic acid-induced abdominal writhing test, treatments with 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole reduced abdominal writhing, while during the formalin test, 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole reduced licking times in response to both neurogenic pain and inflammatory pain, all without demonstrating any antinociceptive effects, as revealed during the tail flick test. 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole also reduced carrageenan-induced paw edema and cell migration during the carrageenan-induced pleurisy test. As demonstrated by the model of the isolated organ, 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole exhibits a vasorelaxant effect attenuated by Nω-nitro-l-arginine methyl ester, 1H-[1,2,4]oxadiazolo[4,3-alpha]quinoxalin-1-one, tetraethylammonium or glibenclamide. 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole also blocked CaCl2 -induced contraction in a dose-dependent manner. Suggesting a safe toxicity profile, 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole reduced the viability of 3T3 cells at higher concentrations and was orally tolerated, despite signs of toxicity in doses of 2000 mg/kg. Lastly, the compounds' analgesic activity might be attributed to the involvement of the NO/cGMP pathway and K+ channels observed in the vasorelaxant effect.
© 2016 John Wiley & Sons A/S.

Entities:  

Keywords:  NO/cGMP pathway; anti-inflammatory effect; antinociceptive effect; pyrazole derivatives; vasorelaxant effect

Mesh:

Substances:

Year:  2016        PMID: 27526659     DOI: 10.1111/cbdd.12838

Source DB:  PubMed          Journal:  Chem Biol Drug Des        ISSN: 1747-0277            Impact factor:   2.817


  2 in total

1.  Molecular docking and pharmacological/toxicological assessment of a new compound designed from celecoxib and paracetamol by molecular hybridization.

Authors:  Daiany P B da Silva; Iziara F Florentino; Dayane M da Silva; Roberta C Lino; Carina S Cardoso; Lorrane K S Moreira; Géssica A Vasconcelos; Daniela C Vinhal; Anna C D Cardoso; Bianca Villavicencio; Hugo Verli; Boniek G Vaz; Luciano M Lião; Luiz C da Cunha; Ricardo Menegatti; Elson A Costa
Journal:  Inflammopharmacology       Date:  2018-07-23       Impact factor: 4.473

Review 2.  Heterocyclic Compounds: Pharmacology of Pyrazole Analogs From Rational Structural Considerations.

Authors:  Rafael Fernades Costa; Larissa Córdova Turones; Keilah Valéria Naves Cavalcante; Ismael Aureliano Rosa Júnior; Carlos Henrique Xavier; Lucimar Pinheiro Rosseto; Hamilton Barbosa Napolitano; Patrícia Ferreira da Silva Castro; Marcos Luiz Ferreira Neto; Gustavo Mota Galvão; Ricardo Menegatti; Gustavo Rodrigues Pedrino; Elson Alves Costa; José Luis Rodrigues Martins; James Oluwagbamigbe Fajemiroye
Journal:  Front Pharmacol       Date:  2021-05-10       Impact factor: 5.810

  2 in total

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