Synthesis and anti-aromatase activity of some new steroidal D-lactones.
Starting from D-seco derivatives of 5-androstene 1-3, the D-homo lactones, 4 and 5, were synthesized. By the Oppenauer oxidation and/or by dehydration of 4 and 5 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or 2,3,5,6-tetrachloro-1,4-benzoquinone (chloranil), the corresponding D-lactones 6-12 were obtained. The structures of 6 and 10 were unambiguously proved by the appropriate X-ray structural analysis. Anti-aromatase assay showed that tested compounds possess inhibition potency, however, two to four times smaller (IC50 from 0.2 to 0.7 microM, respectively) in comparison to aminoglutethimide (AG).
Gasi
Katarina M Penov
KM
Department of Chemistry, Faculty of Sciences, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 3, Serbia and Montenegro, Yugoslavia. sazvon@eunet.yu
Stojanović
Srdjan Z
SZ
Sakac
Marija N
MN
Popsavin
Mirjana
M
Santa
Suzana Jovanović
SJ
Stanković
Slobodanka M
SM
Klisurić
Olivera R
OR
Andrić
Nebojsa
N
Kovacević
Radmila
R
D000818:Animals; D047072:Aromatase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005260:Female; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D051381:Rats; D013055:Spectrophotometry, Infrared; D013256:Steroids / Q000737:chemistry*
D047072:Aromatase Inhibitors; D007783:Lactones; D013256:Steroids