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EnglishSeveral 4- or 5-monosubsituted and 4,5-disubstituted 1,2,3-triazole analogues of the anti-HIV-1 lead com pound [1-[2',5'-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]thymine]-3'-spiro-5''(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO-T) have been prepared and evaluated as inhibitors of HIV-1-induced cytopathicity. These analogues have been prepared by 1,3-diplar cycloaddition of [2,5-bis-O-(tert-butyldimethylsilyl)-beta-D-ribofuranosyl]-3-spiro-5'-(4'-amino- and and 4'-(N-acetylamino)1',2'-oxathiole 2',2'-dioxide) (TSAO) azides to various substituted acetylenes. Several 4- and 5-substituted 1,2,3-triazole-TSAO analogues proved superior to the unsubstituted derivative by 1-2 orders of magnitude. In particular the 5-substituted amido-, (methylamido)-, and (dimethylamido)-1,2,3-triazole derivatives of TSAO were endowed with potent anti-HIV-1 activity (50% effective concentration: 0.056-0.52 mu M). They show a similar resistance spectrum as previously noted for TSAO-T and related derivatives.
ALVAREZ, R., VELAZQUEZ, S., SANFELIX, A., AQUARO, S., DECLERCQ, E., PERNO, C.F., et al. (1994). 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY. JOURNAL OF MEDICINAL CHEMISTRY, 37(24), 4185-4194.
| Tipologia: | Articolo su rivista |
| Citazione: | ALVAREZ, R., VELAZQUEZ, S., SANFELIX, A., AQUARO, S., DECLERCQ, E., PERNO, C.F., et al. (1994). 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY. JOURNAL OF MEDICINAL CHEMISTRY, 37(24), 4185-4194. |
| Altre informazioni significative: | 10 |
| IF: | Con Impact Factor ISI |
| Lingua: | English |
| Settore Scientifico Disciplinare: | Settore MED/07 - Microbiologia e Microbiologia Clinica |
| Revisione (peer review): | Sì, ma tipo non specificato |
| Tipo: | Articolo |
| Rilevanza: | Rilevanza internazionale |
| Stato di pubblicazione: | Pubblicato |
| Data di pubblicazione: | 1994 |
| Titolo: | 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY |
| Autori: | |
| Autori: | ALVAREZ, R; VELAZQUEZ, S; SANFELIX, A; AQUARO, S; DECLERCQ, E; PERNO, CF; KARLSSON, A; BALZARINI, J; CAMARASA, MJ |
| Appare nelle tipologie: | 01 - Articolo su rivista |
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