Synthesis and pharmacological screening of some
new pyrimidine and cyclohexenone fused steroidal
derivatives
Research Area:
Faculty of Science
Type of
Publication:
Article
Authors:

AEE Amr

MM Abdulla
Year:
2002
Journal:
INDIAN JOURNAL OF
HETEROCYCLIC CHEMISTRY
Volume:
12
Number:
2
Pages:
129-134
Month:
OCT-DEC
ISSN:
0971-1627
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.