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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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_0039128X_v68_n2_p125_GarridoSantos |
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todo:paper_0039128X_v68_n2_p125_GarridoSantos2023-10-03T14:49:26Z Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane Garrido Santos, G.A. Murray, A.P. Pujol, C.A. Damonte, E.B. Maier, M.S. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_0039128X_v68_n2_p125_GarridoSantos |
| institution |
Universidad de Buenos Aires |
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I-28 |
| repository_str |
R-134 |
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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 Garrido Santos, G.A. Murray, A.P. Pujol, C.A. Damonte, E.B. Maier, M.S. 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. |
| format |
JOUR |
| author |
Garrido Santos, G.A. Murray, A.P. Pujol, C.A. Damonte, E.B. Maier, M.S. |
| author_facet |
Garrido Santos, G.A. Murray, A.P. Pujol, C.A. Damonte, E.B. Maier, M.S. |
| author_sort |
Garrido Santos, G.A. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_0039128X_v68_n2_p125_GarridoSantos |
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