Comin M J, Maier M S, Roccatagliata A J, Pujol C A, Damonte E B
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina.
Steroids. 1999 May;64(5):335-40. doi: 10.1016/s0039-128x(99)00016-1.
Disodium 3beta,21-dihydroxypregn-5-en-20-one disulfate (2), sodium 3beta,21-dihydroxypregn-5-en-20-one 3-sulfate (3), sodium 3beta,21-dihydroxypregn-5-en-20-one 21-sulfate (4), and disodium 3beta,6alpha-dihydroxy-5alpha-pregnan-20-one disulfate (6) have been synthesized and completely characterized for the first time from readily available materials. Sulfation was performed using triethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. Selective sulfation of 3beta,21-dihydroxypregn-5-en-20-one rendered sodium 3beta,21-dihydroxypregn-5-en-20-one 3-sulfate (3) as the major compound. The synthetic sulfated steroids as well as natural disulfated polyhydroxysteroids (7-9) isolated by us from the antarctic ophiuroid Astrotoma agassizii and the synthetic derivatives disodium 2beta,3alpha,21-trihydroxy-(20R)-cholesta-5,24-diene 3-acetate, 2,21-disulfate (7a) and 2beta,3alpha,21-trihydroxy-(20R)-cholesta-5,24-diene (7b) were comparatively evaluated for their inhibitory effect on the replication of one DNA (HSV-2) and two RNA (PV-3, JV) viruses. In general, steroids with sulfate groups at C-21 and C-2 or C-3 were the most effective in their inhibitory action against HSV-2 and also proved to be active against PV-3 and JV.
3β,21 - 二羟基孕甾 - 5 - 烯 - 20 - 酮二硫酸二钠（2）、3β,21 - 二羟基孕甾 - 5 - 烯 - 20 - 酮3 - 硫酸酯钠（3）、3β,21 - 二羟基孕甾 - 5 - 烯 - 20 - 酮21 - 硫酸酯钠（4）以及3β,6α - 二羟基 - 5α - 孕烷 - 20 - 酮二硫酸二钠（6）首次由易得原料合成并得到全面表征。使用三乙胺 - 三氧化硫络合物在二甲基甲酰胺中作为硫酸化试剂进行硫酸化反应。3β,21 - 二羟基孕甾 - 5 - 烯 - 20 - 酮的选择性硫酸化使得3β,21 - 二羟基孕甾 - 5 - 烯 - 20 - 酮3 - 硫酸酯钠（3）成为主要化合物。我们从南极蛇尾类动物阿加西氏星蛇尾中分离得到的合成硫酸化甾体以及天然二硫酸化多羟基甾体（7 - 9），以及合成衍生物2β,3α,21 - 三羟基 - (20R) - 胆甾 - 5,24 - 二烯3 - 乙酸酯2,21 - 二硫酸酯（7a）和2β,3α,21 - 三羟基 - (20R) - 胆甾 - 5,24 - 二烯（7b），对它们抑制一种DNA病毒（单纯疱疹病毒2型，HSV - 2）和两种RNA病毒（脊髓灰质炎病毒3型，PV - 3；日本脑炎病毒，JV）复制的效果进行了比较评估。一般来说，在C - 21和C - 2或C - 3处带有硫酸酯基团的甾体对HSV - 2的抑制作用最为有效，并且对PV - 3和JV也具有活性。
