title: Synthesis and anti-aromatase activity of some new steroidal D-lactones.
abstract: 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).
authors.affiliation: Department of Chemistry, Faculty of Sciences, University of Novi Sad, 21000 Novi Sad, Trg Dositeja Obradovića 3, Serbia and Montenegro, Yugoslavia. sazvon@eunet.yu
authors.forename: Katarina M Penov
authors.initials: KM
authors.lastname: Gasi
authors.forename: Srdjan Z
authors.initials: SZ
authors.lastname: Stojanović
authors.forename: Marija N
authors.initials: MN
authors.lastname: Sakac
authors.forename: Mirjana
authors.initials: M
authors.lastname: Popsavin
authors.forename: Suzana Jovanović
authors.initials: SJ
authors.lastname: Santa
authors.forename: Slobodanka M
authors.initials: SM
authors.lastname: Stanković
authors.forename: Olivera R
authors.initials: OR
authors.lastname: Klisurić
authors.forename: Nebojsa
authors.initials: N
authors.lastname: Andrić
authors.forename: Radmila
authors.initials: R
authors.lastname: Kovacević
mesh_terms: 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*
chemical_list: D047072:Aromatase Inhibitors; D007783:Lactones; D013256:Steroids