Collect. Czech. Chem. Commun. 2000, 65, 1597-1608
https://doi.org/10.1135/cccc20001597

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

Abstract

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.