Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
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...
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2003
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v68_n2_p125_GarridoSantos http://hdl.handle.net/20.500.12110/paper_0039128X_v68_n2_p125_GarridoSantos |
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paper:paper_0039128X_v68_n2_p125_GarridoSantos2023-06-08T15:03:17Z Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane Antiviral activity Sulfated steroids Synthesis antivirus agent cholestane derivative disodium 2beta,3alpha dihydroxy 5alpha cholestane disulfate n,n dimethylformamide sodium 2beta acetoxy 3alpha hydroxy 5alpha cholestane 3 sulfate sodium 2beta,3alpha dihydroxy 5alpha cholestane 2 sulfate sodium 2beta,3alpha dihydroxy 5alpha cholestane 3 sulfate sodium 3alpha acetoxy 2beta hydroxy 5alpha cholestane 2 sulfate steroid sulfur derivative unclassified drug acetylation animal cell antiviral activity article controlled study Dengue virus drug efficacy drug screening drug synthesis Herpes simplex virus 2 Junin virus nonhuman nuclear magnetic resonance spectroscopy sulfation virus inhibition virus replication Human herpesvirus 2 Simplexvirus 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. © 2002 Elsevier Science Inc. All rights reserved. 2003 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v68_n2_p125_GarridoSantos http://hdl.handle.net/20.500.12110/paper_0039128X_v68_n2_p125_GarridoSantos |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Antiviral activity Sulfated steroids Synthesis antivirus agent cholestane derivative disodium 2beta,3alpha dihydroxy 5alpha cholestane disulfate n,n dimethylformamide sodium 2beta acetoxy 3alpha hydroxy 5alpha cholestane 3 sulfate sodium 2beta,3alpha dihydroxy 5alpha cholestane 2 sulfate sodium 2beta,3alpha dihydroxy 5alpha cholestane 3 sulfate sodium 3alpha acetoxy 2beta hydroxy 5alpha cholestane 2 sulfate steroid sulfur derivative unclassified drug acetylation animal cell antiviral activity article controlled study Dengue virus drug efficacy drug screening drug synthesis Herpes simplex virus 2 Junin virus nonhuman nuclear magnetic resonance spectroscopy sulfation virus inhibition virus replication Human herpesvirus 2 Simplexvirus |
| spellingShingle |
Antiviral activity Sulfated steroids Synthesis antivirus agent cholestane derivative disodium 2beta,3alpha dihydroxy 5alpha cholestane disulfate n,n dimethylformamide sodium 2beta acetoxy 3alpha hydroxy 5alpha cholestane 3 sulfate sodium 2beta,3alpha dihydroxy 5alpha cholestane 2 sulfate sodium 2beta,3alpha dihydroxy 5alpha cholestane 3 sulfate sodium 3alpha acetoxy 2beta hydroxy 5alpha cholestane 2 sulfate steroid sulfur derivative unclassified drug acetylation animal cell antiviral activity article controlled study Dengue virus drug efficacy drug screening drug synthesis Herpes simplex virus 2 Junin virus nonhuman nuclear magnetic resonance spectroscopy sulfation virus inhibition virus replication Human herpesvirus 2 Simplexvirus Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane |
| topic_facet |
Antiviral activity Sulfated steroids Synthesis antivirus agent cholestane derivative disodium 2beta,3alpha dihydroxy 5alpha cholestane disulfate n,n dimethylformamide sodium 2beta acetoxy 3alpha hydroxy 5alpha cholestane 3 sulfate sodium 2beta,3alpha dihydroxy 5alpha cholestane 2 sulfate sodium 2beta,3alpha dihydroxy 5alpha cholestane 3 sulfate sodium 3alpha acetoxy 2beta hydroxy 5alpha cholestane 2 sulfate steroid sulfur derivative unclassified drug acetylation animal cell antiviral activity article controlled study Dengue virus drug efficacy drug screening drug synthesis Herpes simplex virus 2 Junin virus nonhuman nuclear magnetic resonance spectroscopy sulfation virus inhibition virus replication Human herpesvirus 2 Simplexvirus |
| description |
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. © 2002 Elsevier Science Inc. All rights reserved. |
| title |
Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane |
| title_short |
Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane |
| title_full |
Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane |
| title_fullStr |
Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane |
| title_full_unstemmed |
Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane |
| title_sort |
synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane |
| publishDate |
2003 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v68_n2_p125_GarridoSantos http://hdl.handle.net/20.500.12110/paper_0039128X_v68_n2_p125_GarridoSantos |
| _version_ |
1768543410037194752 |