Affiliation:
1. Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain
2. Departamento de Farmacología, Universidad de Alcalá, 28871 Alcalá de Henares, Madrid, Spain
3. Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000 Leuven, Belgium
Abstract
Several 5- N-alkyl and 5- N,N-dialkylcarbamoyl substituted analogues of the anti-human immunodeficiency virus (HIV) type 1 lead compound[1-[2‘,5’-bis- O-( tert-butyldimethylsilyl)-β-D-ribofuranosyl]-5-( N,N-dimethylcarbamoyl)-1,2,3-triazole]-3‘-spiro-5“-(4”-amino-1“,2”-oxathiole-2“,2”-dioxide) have been prepared and evaluated as inhibitors of HIV-1 replication. A new regiospecific synthetic procedure is described. The compounds were prepared by cycloaddition of the appropriate glycosylazide to 2-oxo-alkylidentriphenyl-phosphoranes, followed by treatment with primary or secondary amines, to yield, exclusively, 5-substituted 1,2,3-triazole-TSAO analogues. Several 5-substituted 1,2,3-triazole-TSAO derivatives proved to be potent inhibitors of HIV-1 replication with higher antiviral selectivity than that of the parent TSAO prototype.
Cited by
249 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献
1. Design, Synthesis, Computational, and In Vitro Cytotoxic Potential of Novel 5,7,8,9-Tetrahydrotetrazolo[5,1-b]quinazolines Analogs;Russian Journal of Bioorganic Chemistry;2024-04
2. An efficient synthesis of 4,5-disubstituted 1,2,3-triazoles by three-component reaction between sodium azide, ethyl cyanoacetate or malonitrile and arylglyoxals;Synthetic Communications;2024-02-11
3. Synthesis of azepines, diazepines, triazepines, oxepines, oxazepines, and thiapines;Synthesis of 6- and 7-Membered Heterocycles;2024
4. Hybrid pyrazoline-triazole fluorescent dyes: Synthesis, photophysics, electrochemical, and antioxidative activity;Journal of Photochemistry and Photobiology A: Chemistry;2023-10
5. Organocatalytic [3+2] Cycloaddition Reaction: Synthesis of Fully Decorated Sulfonyl 1,2,3‐Triazoles as Potent EGFR Targeting Anticancer Agents**;ChemistrySelect;2023-09-07