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: Katarina M Penov Gasi, Srdjan Z Stojanović, Marija N Sakac, Mirjana Popsavin, Suzana Jovanović Santa, Slobodanka M Stanković, Olivera R Klisurić, Nebojsa Andrić, Radmila Kovacević
• Journal: Steroids (Steroids) Vol. 70 Issue 1 Pg. 47-53 (Jan 2005) ISSN: 0039-128X [Print] United States
• PMID: 15610896 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Aromatase Inhibitors
• Lactones
• Steroids

Topics

• Animals
• Aromatase Inhibitors (chemical synthesis, chemistry, pharmacology)
• Female
• Lactones (chemical synthesis, chemistry, pharmacology)
• Magnetic Resonance Spectroscopy
• Mass Spectrometry
• Models, Molecular
• Rats
• Spectrophotometry, Infrared
• Steroids (chemistry)