Synthesis and Anti-inflammatory Activity of Steroidal 17-Yl-α-Oxothiocarboxamides and Related Compounds

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,...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 27; no. 6; pp. 1352 - 1359
Main Authors OBAYASHI, MIKIHIKO, KUZUNA, SEIJI, NOGUCHI, SHUNSAKU
Format Journal Article
LanguageEnglish
Published The Pharmaceutical Society of Japan 1979
Subjects
anti-inflammatory activity
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Summary: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.27.1352