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Arzneimittelforschung 2011; 61(3): 186-190
DOI: 10.1055/s-0031-1296187
Analgesics · Anti-inflammatories · Antiphlogistics · Antirheumatic Drugs
Editio Cantor Verlag Aulendorf (Germany)

Synthesis and screening of cyclooxygenase inhibitory activity of some 1,3-dioxoisoindoline derivatives

Murat Çizmecioğlu
1   Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University Bornova, Izmir, Turkey
,
Varol Pabuççuoğlu
1   Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University Bornova, Izmir, Turkey
,
Petek Ballar
2   Department of Biochemistry, Faculty of Pharmacy, Ege University Bornova, Izmir, Turkey
,
Aysun Pabuççuoğlu
2   Department of Biochemistry, Faculty of Pharmacy, Ege University Bornova, Izmir, Turkey
,
Zeynep Soyer
1   Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ege University Bornova, Izmir, Turkey
› Author Affiliations
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Publication History

Publication Date:
28 November 2011 (online)

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Abstract

In this study, 15 compounds bearing N,N-phthaloylacetamide structure designed by the molecular simplification approach based on thalidomide structure were synthesized and evaluated for inhibitory potencies against cyclooxgenase (COX) isoenzymes, namely COX-1 and COX-2. The results suggested that the N,N-phthaloylacetamide structure, as a primary amide, has inhibitory activity against cyclooxygenase isoenzymes with a higher COX-1 selectivity. The conversion of the primary amide to secondary or tertiary derivatives lowered the potency but favored the COX-2 selectivity thus yielding the compounds with stronger COX-2 inhibiting activity.

Key words

Anti-inflammatories - Cyclooxygenase - 1,3-Dioxoisoindolines, inhibitory activity, synthesis - Thalidomide derivatives
 

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