Antiandrogenic activity of certain steroid spirolactones

Synthesis of new α-spiroheteryl-fused butanolides

“…While continuing our investigations in the series of 4-alkoxymethylbutanolides [3], we realized the bromination of 4-alkoxymethyl-2-ethoxycarbonylbutanolides 1a,b with bromine in dry carbon tetrachloride at room temperature with the formation of high yields (88-89%) of the corresponding 2-bromo derivatives 2a,b. O ROCH 2 COOEt O Br 2 O ROCH 2 COOEt Br O 1a,b 2a,b 1, 2 a R = Pr, b R = BuSuch compounds can be used as synthons for the synthesis of various spiro-fused butanolide-containing heterocycles, among which highly biologically active compounds [8,9] and also natural compounds of plant origin [10,11] have been found.In fact, in the reaction of equimolar amounts of the bromides 2a,b with thiocarbamide or its monoarylsubstituted derivative in dry acetone under mild conditions (20°C for 1 h, boiling for 1 h) high yields of previously undescribed spiroheteryl-fused butanolides with a new structure, 8 …”

“…Such compounds can be used as synthons for the synthesis of various spiro-fused butanolide-containing heterocycles, among which highly biologically active compounds [8,9] and also natural compounds of plant origin [10,11] have been found.…”

Syntheses based on 8-substituted 3-bromoacetyl-3,8-dimethyl-2,7-dioxaspiro[4,4]nonane-1,6-diones

“…In particular, thiazolyl, benzimidazolyl, and triazolyl derivatives of 4-butanolides exhibit anti-inflammatory, antitumor, cardiovascular activity and a muscle relaxant effect [1]. Especially interesting heterocyclic compounds are those which contain a spiro-linked butanolide moiety and which are a structural unit for various natural substances [2][3][4], since individual representatives of this class are used in medicine for edema, ascites, and nephrotic syndrome [5,6]. From the above we see the importance of studies in the field of spiro-linked heterocyclic butanolides.…”