The synthesis in excellent yields of 2,3-dihydro-6-mercapto-1,3,5-triphenyl-2-thioxo-4(3H)-pyrimidinone 3 and 5-ethoxycarbonyl-2,3-dihydro-6-mercapto-1,3-diphenyl-2-thioxo-4(3H)-pyrimidinone 4 by reaction of Me phenylacetate or di-Et malonate, resp., with Ph isothiocyanate (3 molar equivalents) and sodium hydride (2 molar equivalents) in DMF soln. is described. Acylation of 3 and 4 with acyl chlorides gave, generally in satisfactory yields, 6-acylthio derivs. Some of the above compds. showed a platelet antiaggregating activity in vitro superior or comparable to that of acetylsalicylic acid, as well as remarkable antiinflammatory, antiarrhythmic, local anesthetic and antihyperlipidemic activities in rats and in mice. Weak anticonvulsant and hypoglycemic activities were also detected.
5-Substituted 2,3-dihydro-6-mercapto-1,3-diphenyl-2-thioxo-4(3H)-pyrimidinones and their 6-(acylthio) derivatives with platelet antiaggregating, antiinflammatory, antiarrhythmic, antihyperlipidemic and other activities.
RANISE, ANGELO;BRUNO, OLGA;BONDAVALLI, FRANCESCO;SCHENONE, SILVIA;
1994-01-01
Abstract
The synthesis in excellent yields of 2,3-dihydro-6-mercapto-1,3,5-triphenyl-2-thioxo-4(3H)-pyrimidinone 3 and 5-ethoxycarbonyl-2,3-dihydro-6-mercapto-1,3-diphenyl-2-thioxo-4(3H)-pyrimidinone 4 by reaction of Me phenylacetate or di-Et malonate, resp., with Ph isothiocyanate (3 molar equivalents) and sodium hydride (2 molar equivalents) in DMF soln. is described. Acylation of 3 and 4 with acyl chlorides gave, generally in satisfactory yields, 6-acylthio derivs. Some of the above compds. showed a platelet antiaggregating activity in vitro superior or comparable to that of acetylsalicylic acid, as well as remarkable antiinflammatory, antiarrhythmic, local anesthetic and antihyperlipidemic activities in rats and in mice. Weak anticonvulsant and hypoglycemic activities were also detected.
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