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Synthesis and anti-inflammatory activity of steroidal 17-yl-.ALPHA.-oxothiocarboxamides and related compounds.
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1979
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Steroidal 17-Yl-.alpha.-oxothiocarboxamidesPharmacotherapyInflammationMolecular PharmacologyMedicinal ChemistryCotton Pellet TestSteroid MetabolismCarrageenin Edema TestOxysterolAllergyBiochemistryChronic InflammationPharmacological AgentPharmacologyInflammatory DiseaseWillgerodt-kindler ReactionAnti-inflammatoryNatural SciencesMedicineDrug Discovery
The Willgerodt-Kindler reaction of 21-chloro-20-ketosteroids (5) or sodium 21-thiosulfate derivatives of 20-ketosteroids (6) with sulfur in secondary amines gave the corresponding steroidal α-oxothiocarboxamides (3) in good yields. Among these compounds (3), 11β, 17α-dihydroxy-21-morpholinopregna-1, 4-diene-3, 20-dione-21-thione (3a) and 11β, 17α-dihydroxy-21-morpholinopregn-4-ene-3, 20-dione-21-thione (3b) showed potent anti-inflammatory activities comparable to or a little less than those of the parent compounds, prednisolone and hydrocortisone, respectively, in the carrageenin edema test in rats. 3a also showed potent activity in the granuloma pouch test in rats but much less activity in the cotton pellet test in rats. These results suggest that 3a might be more active against acute or subacute inflammation than against chronic inflammation.