MURRAY Ana paula
Synthesis and antiviral activity evaluation of sulfated and acetylated derivatives of 2ß,3a-dihydroxy-5a-cholestane
GARRIDO SANTOS, GUSTAVO; ANA PAULA MURRAY; CARLOS PUJOL; ELSA DAMONTE; MAIER, MARTA SILVIA
Año: 2003 vol. 68 p. 125 - 132
Five new steroid sulfates, sodium 2b,3a-dihydroxy-5a-cholestane 3-sulfate (6), sodium 2b,3a-dihydroxy-5a-cholestane 2-sulfate (7), disodium 2b,3a-dihydroxy-5a-cholestane disulfate (8), sodium 3a-acetoxy-2b-hydroxy-5a-cholestane 2-sulfate (12), and sodium 2b-acetoxy-3a-hydroxy-5a-cholestane 3-sulfate (13), have been synthesized starting from 3b-hydroxy-5a-cholestane (1). The synthetic steroids were completely characterized by 1D and 2D NMR and FAB-MS spectra. Sulfation was performed using triethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The sulfated steroids were comparatively evaluated for their inhibitory effect on the replication of herpes simplex virus type 2 (HSV-2). Compounds 7 and 8 were the most effective in their inhibitory action against HSV-2. The disulfated steroid 8 also proved to be active against DEN-2 and JV.