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1,2,3-Triazole-[2,5-Bis-O-(tert-butyldimethylsilyl)-.beta.-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO) Analogs: Synthesis and Anti-HIV-1 Activity
Abstract
Several 4- or 5-monosubsituted and 4,5-disubstituted 1,2,3-triazole analogues of the anti-HIV-1 lead compound [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 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 microM). They show a similar resistance spectrum as previously noted for TSAO-T and related derivatives.
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Citations
Cited by
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Bock, V. D., Hiemstra, H., & van Maarseveen, J. H. (2006) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200500483 · Cited by 1,452
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Synthesis and antifungal activity of 1,2,3-triazole containing fluconazole analogues
Aher, N. G., Pore, V. S., Mishra, N. N., Kumar, A., Shukla, P. K., Sharma, A., & Bhat, M. K. (2009) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2008.12.026 · Cited by 328
Metadata
- Authors
- Alvarez, R., Velazquez, S., San-Felix, A., Aquaro, S., Clercq, E. D., Perno, C.-F., Karlsson, A., Balzarini, J., & Camarasa, M. J.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1994-11
- Volume
- 37
- Issue
- 24
- Pages
- 4185-4194
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W1976923865
- Cited by
- 751
- References
- 0
- FWCI
- 3.13
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: 1,2,3-Triazole-[2,5-Bis-O-(tert-butyldimethylsilyl)-.beta.-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO) Analogs: Synthesis and Anti-HIV-1 Activity. https://app.cochat.ai/papers/10.1021/jm00050a015
- The paper
- Alvarez, R., Velazquez, S., San-Felix, A., Aquaro, S., Clercq, E. D., Perno, C.-F., Karlsson, A., Balzarini, J., & Camarasa, M. J. (1994). 1,2,3-Triazole-[2,5-Bis-O-(tert-butyldimethylsilyl)-.beta.-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO) Analogs: Synthesis and Anti-HIV-1 Activity. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm00050a015
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