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2β,3α-二羟基-5α-胆甾烷的硫酸化和乙酰化衍生物的合成及其抗病毒活性

Synthesis and antiviral activity of sulfated and acetylated derivatives of 2beta,3alpha-dihydroxy-5alpha-cholestane.

作者信息

Santos Gustavo A Garrido, Murray Ana P, Pujol Carlos A, Damonte Elsa B, Maier Marta S

机构信息

Departamento de Qui;mica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Argentina.

出版信息

Steroids. 2003 Feb;68(2):125-32. doi: 10.1016/s0039-128x(02)00166-6.

DOI:10.1016/s0039-128x(02)00166-6
PMID:12606002
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7157925/
Abstract

Five new steroid sulfates, sodium 2beta,3alpha-dihydroxy-5alpha-cholestane 3-sulfate (6), sodium 2beta,3alpha-dihydroxy-5alpha-cholestane 2-sulfate (7), disodium 2beta,3alpha-dihydroxy-5alpha-cholestane disulfate (8), sodium 3alpha-acetoxy-2beta-hydroxy-5alpha-cholestane 2-sulfate (12), and sodium 2beta-acetoxy-3alpha-hydroxy-5alpha-cholestane 3-sulfate (13), have been synthesized starting from 3beta-hydroxy-5alpha-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.

摘要

从3β-羟基-5α-胆甾烷（1）出发，合成了五种新的甾体硫酸盐，即2β,3α-二羟基-5α-胆甾烷3-硫酸盐钠盐（6）、2β,3α-二羟基-5α-胆甾烷2-硫酸盐钠盐（7）、2β,3α-二羟基-5α-胆甾烷二硫酸盐二钠盐（8）、3α-乙酰氧基-2β-羟基-5α-胆甾烷2-硫酸盐钠盐（12）和2β-乙酰氧基-3α-羟基-5α-胆甾烷3-硫酸盐钠盐（13）。通过一维和二维核磁共振光谱以及快原子轰击质谱对合成的甾体进行了全面表征。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剂进行硫酸化反应。对硫酸化甾体对单纯疱疹病毒2型（HSV-2）复制的抑制作用进行了比较评估。化合物7和8对HSV-2的抑制作用最为有效。二硫酸化甾体8对登革热病毒2型（DEN-2）和日本脑炎病毒（JV）也有活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/a894f5eddfb1/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/516bb9833101/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/fd31a005db1d/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/85f43bfd4f9b/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/683c4ade670b/sc3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/bb95502095da/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/a894f5eddfb1/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/516bb9833101/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/fd31a005db1d/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/85f43bfd4f9b/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/683c4ade670b/sc3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/bb95502095da/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a2b3/7157925/a894f5eddfb1/gr3.jpg

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