Collect. Czech. Chem. Commun. 2000, 65, 1597-1608

Synthesis of Symmetrical Bis-Steroid Pyrazines Connected via D-Rings

Ivan Černý*, Vladimír Pouzar, Miloš Buděšínský and Pavel Drašar

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


Bis-steroid pyrazines fused through rings D of the steroid skeleton were synthesized. Methods for the preparation of the corresponding rings A fused derivatives (cephalostatin type) were checked on simple androstanes and then a symmetrical D fused analogue, 5α-androstano[16'',17''-5',6']pyrazino[2',3'-16,17]-5α-androstane-3β,3''b-diol, was prepared. Partially substituted bis-steroid pyrazines in both series were prepared and their use for the preparation of higher fused compounds was discussed. No significant cytostatic activity was found on parent bis-steroid pyrazines both A and D fused.

Keywords: Steroids; Cephalostatin analogues; Symmetrical bis-steroid pyrazines; NMR spectroscopy; Cytostatic activity.

References: 15 live references.