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.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Cyclooxygenase 1 / metabolism
-
Cyclooxygenase 2 Inhibitors / chemical synthesis
-
Cyclooxygenase 2 Inhibitors / pharmacology
-
Cyclooxygenase Inhibitors / chemical synthesis*
-
Cyclooxygenase Inhibitors / pharmacology*
-
Drug Design
-
Indicators and Reagents
-
Indoles / chemical synthesis*
-
Indoles / pharmacology*
-
Magnetic Resonance Spectroscopy
-
Spectrophotometry, Infrared
-
Structure-Activity Relationship
-
Thalidomide / analogs & derivatives*
-
Thalidomide / chemistry*
-
Thalidomide / pharmacology
Substances
-
Cyclooxygenase 2 Inhibitors
-
Cyclooxygenase Inhibitors
-
Indicators and Reagents
-
Indoles
-
Thalidomide
-
Cyclooxygenase 1