Tropical Journal of Pharmaceutical Research

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Research Article

Antinociceptive Activity of Thymoquinone and its Structural Analogues: A Structure-Activity Relationship Study

Damião P de Sousa^1*, Franklin FF Nóbrega², Camila CMP Santos², Rubens B Benedito², Ygor W Vieira³, Marciana P Uliana³, Timothy J Brocksom³ and Reinaldo N de Almeida²

¹Laboratório de Química de Produtos Naturais e Sintéticos Bioativos (LAPROBIO), Departamento de Fisiologia, Universidade Federal de Sergipe, CEP 49100-000, São Cristóvão, Sergipe, ²Laboratório de Tecnologia Farmacêutica/Universidade Federal da Paraíba, Caixa Postal 5009, CEP 58051–970, João Pessoa, Paraíba, ³Laboratório de Química Bio-Orgânica, Departamento de Química, Universidade Federal de São Carlos, Caixa Postal 676, 13565-905 São Carlos, SP, Brazil..

*For correspondence: Email: damiao_desousa@yahoo.com.br

Received: 9 October 2011 Revised accepted: 19 June 2012

Tropical Journal of Pharmaceutical Research, August 2012; 11(4): 605-610

http://dx.doi.org/10.4314/tjpr.v11i4.11

Abstract

Purpose: To investigate the structural features that influence the antinociceptive activity of thymoquinone and their structural analogues.

Methods: The quinones were prepared by an oxidation procedure using molecular oxygen and catalysis with [Co^II(salen)] from the respective phenols. The antinociceptive activity of para-benzoquinones (10 mg/kg, ip) was evaluated using formalin test in mice. Vehicle (5 % Tween 80) or morphine (10 mg/kg) were used as control group and standard drug, respectively. The amount of time spent licking the injected paw was considered as the nociceptive response.

Results: Among the compounds tested, five para-benzoquinones showed antinociceptive activity. The 2-isopropyl-para-benzoquinone presented the highest potency in first and second phases and produced a near-maximal inhibition (p < 0.001) in the formalin test, similar to morphine (p < 0.001).

Conclusion: Our experimental results show that by appropriate structural modification of para-benzoquinones it may be possible to develop novel analgesic drugs.

Keywords: Quinones, Antinociceptive activity, Analgesic, Central nervous system, Structure-activity relationship, Medicinal plant.