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Arzneimittelforschung 2008; 58(8): 398-404
DOI: 10.1055/s-0031-1296527
Analgesics · Anti-inflammatories · Antiphlogistics · Antirheumatic Drugs
Editio Cantor Verlag Aulendorf (Germany)

Synthesis and Evaluation of Analgesic, Anti-Inflammatory and Antioxidant Activities of New 6-Acyl-3-alkyl-5-methyl-2(3H) -benzoxazolones

Meric Koksal
1   Yeditepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Istanbul, Turkey
,
Nesrin Gokhan Kelekci
2   Hacettepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara, Turkey
,
Guldem Olguner Mercanoglu
3   Yeditepe University, Faculty of Pharmacy, Department of Pharmacology, Istanbul, Turkey
,
Hakki Erdogan
2   Hacettepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Ankara, Turkey
› Author Affiliations
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Publication History

Publication Date:
15 December 2011 (online)

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Abstract

A new series of 6-acyl-3-alkyl-5-methyl-2(3H)-benzoxazolones have been obtained starting from 5-methyl-2(3H)-benzoxazolone. All the compounds have been characterized by IR, 1H-NMR and mass spectroscopy. The new compounds were screened for analgesic and anti-inflammatory activities and ulcerogenic effect. The in vitro antioxidant capacity of the synthesized compounds were tested by the nitric oxide radical scavenging assay. Most of the compounds showed antiinflammatory activity. Among them, 3-[4-(4-fluorophenyl)piperazinomethyl]-6-(3-chlorobenzoyl)-5-methyl-2(3H)-benzoxazolone (3j) was found more potent than the reference drug indometacin (CAS 53-86-1) with 41.66% decrease in edema. Compared with the control, some of the compounds exhibited analgesic effects. Similar to the anti-inflammatory activity results, compound 3j showed the highest analgesic profile with 48.56% inhibition. No active hemorragic focus was observed in the microscopic evaluation in the ulcerogenic effect studies of the tested compounds. 6-(3-Chlorobenzoyl)-5-methyl-2(3H)-benzoxazolone (2b) and 3-[4-(4-fluorophenyl-piperazino)methyl]-6-(3-chlorobenzoyl)-5-methyl-2(3H)-benzoxazolone (3j) showed nearly maximum antioxidant activity compared to ascorbic acid (CAS 50-81-7) with IC50 values of 27.6 and 30.1 μg/mL, respectively.

Key words

Analgesics - Anti-inflammatories - Antioxidants - 2 (3H) -Benzoxazolones, - N-alkylation
 

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