ORIGINAL ARTICLE
Year : 2012  |  Volume : 11  |  Issue : 1  |  Page : 22-30

Potent anti-inflammatory and analgesic activities of new derivatives of chalcone, pyridine, pyrazole, and isoxazole incorporated into 5,6,7,8-tetrahydronaphthalene


1 Applied Organic Chemistry Department, National Research Centre, Cairo, Egypt
2 Pharmacology Department, Faculty of Veterinary Medicine, Cairo University, Giza, Egypt

Correspondence Address:
Nehal A. Hamdy
Applied Organic Chemistry Department, National Research Centre, Dokki, 12622 Cairo
Egypt
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Source of Support: None, Conflict of Interest: None


DOI: 10.7123/01.EPJ.0000416046.32749.90

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Objective

Synthesis of new series of 5,6,7,8-tetrahydronaphthalene derivatives conjugated with chalcone, pyridine, pyrazole and isoxazole functionalities hoping to circumvent the unwanted ulcerogenic and other side effects of the already used nonsteroidal anti-inflammatory drugs.

Background

Most currently used nonsteroidal anti-inflammatory drugs (NSAIDs) suffer from limitation in their therapeutic uses, since they cause gastrointestinal and renal side effects related to inhibition of cyclooxygenase1 (Cox1) in tissues where prostaglandins exert physiological effects.

Methodology

Reaction of 2-acetyl tetralin (1) with some aromatic aldehydes in the presence of malononitrile yielded 2-amino-3-cyanopyridine derivatives 2a–c. Condensation of compound 1 with aromatic aldehydes afforded the chalcone derivatives 3a–c. Then, compound 3a reacted with hydrazine hydrate or phenyl hydrazine and yielded pyrazoline derivatives 4 or 5, respectively. Also, the reaction of compound 3c with hydroxylamine hydrochloride afforded the isoxazole derivative 6. Anti-inflammatory properties of the synthesized compounds were evaluated in vivo utilizing formalin induced paw edema method in rats, analgesic activities were tested via both hot plate and writhing methods.

Results

Derivatives 2c and 3c revealed promising results when the anti-inflammatory, analgesic, and ulcerogenic activities of the synthesized compounds were evaluated. All of the compounds induced significant central and peripheral analgesia. The derivatives 2a, 2c, 3a, 3b, 3c, 5, and 6 showed higher activity than the standard ibuprofen.



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