The preparation and chemical properties of 3-acyl-5-arylidene-4-hydroxy-2,5-dihydro-2-oxothiophens, a new class of immunosuppressive agent
- 1 January 1968
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- Vol. 12, 1501-1505
- https://doi.org/10.1039/j39680001501
Abstract
The title compounds, which act as immunosuppressive agents by interference with the cell line responsible for antibody synthesis, have been prepared by the condensation of aromatic aldehydes with 3-acetyl-2,5-dihydro-4-hydroxy-2-oxothiophen. Immunosuppressive activity was greatly influenced by substituents in the benzene ring. The corresponding 3-acyl-2,5-dihydro-4-hydroxy-2-oxo-5-p-tolylazothiophens were inactive. The condensation products of 3-acetyl-5-arylidene-2,5-dihydro-4-hydroxy-2-oxothiophens with primary aliphatic or aromatic amines have been shown to be 3-(1-alkyl- or aryl-aminoethylidene)-5-arylidene-2,4-dioxotetrahydrothiophens. 3-Acetyl-5-p-fluorobenzylidene-2,5-dihydro-4-hydroxy-2-oxothiophen has been shown to isomerize in alkali or daylight to 1-acetyl-4-p-fluorophenyl-2-hydroxy-5-oxo-3-thiocyclopentene.Keywords
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