info:eu-repo/semantics/article
Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
Fecha
2003-02Registro en:
Garrido Santos, Gustavo A.; Murray, Ana Paula; Pujol, Carlos Alberto; Damonte, Elsa Beatriz; Maier, Marta Silvia; Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane; Elsevier Science Inc; Steroids; 68; 2; 2-2003; 125-132
0039-128X
CONICET Digital
CONICET
Autor
Garrido Santos, Gustavo A.
Murray, Ana Paula
Pujol, Carlos Alberto
Damonte, Elsa Beatriz
Maier, Marta Silvia
Resumen
Five new steroid sulfates, sodium 2β,3α-dihydroxy-5α-cholestane 3-sulfate (6), sodium 2β,3α-dihydroxy-5α-cholestane 2-sulfate (7), disodium 2β,3α-dihydroxy-5α-cholestane disulfate (8), sodium 3α-acetoxy-2β-hydroxy-5α-cholestane 2-sulfate (12), and sodium 2β-acetoxy-3α-hydroxy-5α-cholestane 3-sulfate (13), have been synthesized starting from 3β-hydroxy-5α-cholestane (1). The synthetic steroids were completely characterized by one-dimensional and two-dimensional NMR and FABMS 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.