Abstract
Several new compounds containing cyclohexenone, pyrimidine, thiopyrimidine, aminopyrimidine ring fused to steroidal moiety were synthesized as androgenic anabolic and antiinflammatory agents. Condensation of urea, thiourea and guanidine hydrochloride with arylmethylene 1 gave the corresponding pyrimidine derivatives 3-5, respectively. Oxidation with Moffatt reagent (DMSO/DCC/TFA) afforded the oxidized compounds 6-8, respectively. Also compound 2 reacted with urea, thiourea and guanidine hydrochloride to give the corresponding pyrimidine derivatives 9a-c, respectively, which were subjected to Moffat, Oppenauer and modified Oppenauer oxidation to give compounds 10a-c, 11a-c and 12a-c respectively. Compounds 1 or 2 were condensed with cyanoguanidine hydrochloride to give corresponding 13a-d and 14, respectively. Also, compounds 1 or 2 were condensed with ethyl acetoacetate or acetyl acetone to give compounds 15a-i and 16a-b, respectively, which were treated with p-toluene sulfonyl chloride to give compounds 17a-d and 18a,b respectively. Compounds 15 were oxidized (Moffatt) to afford compound 19a-d which were treated with dichlorodicyanoquinone (DDQ) to yield compounds 20a-d, respectively, Compounds 16 were converted to compounds 21 and 22 by oxidation and compound 22 treated with chloranil to yield compounds 23. The pharmacological screening showed that many of these compounds exhibited good androgenic, anabolic and anti inflammatory activity.