Synthesis and Antiviral Activity of 1,5-and 1,3-Dialkyl-1,2,4-triazoleC-Nucleosides Derived from 1-(Chloroalkyl)-1-aza-2-azoniaallene Salts
- 1 September 1999
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 18 (9) , 1985-1994
- https://doi.org/10.1080/07328319908044859
Abstract
Reactions of α, α′-dichloroazo compounds 2 with SbCl5 gave 1-(chloroalkyl)-1-aza-2-azoniaallene salts 3 as reactive intermediates. Cycloadditions of 3 with the ribofuranosyl cyanide 4 afforded the β-D-ribofuranosyl-1,2,4-triazolium salts 5, which rearranged spontaneously to salts 6. Hydrolysis of 6 gave the 1,2,4-triazole C-nucleosides 7, which yielded the free nucleosides 8 after deblocking. Analogously, 12 was prepared from the cycloaddition of 4 with the α-chloroazo compound 10 in the presence of SbCl5. Deblocking of 12 with sodium methoxide afforded 13. Compounds 8a,b,e,f and 13 were tested against HIV-1, HIV-2, HSV-1 and HSV-2 and were found to be inactive.Keywords
This publication has 24 references indexed in Scilit:
- Syntheses of C- and N-nucleosides from 1-aza-2-azoniaallene and 1,3-diaza-2-azoniaallene saltsJournal of the Chemical Society, Perkin Transactions 1, 1998
- Synthesis of C-glycosides of biological interestPublished by Springer Nature ,1997
- Nucleophilic C-glycosyl donors for C-glycoside synthesisPublished by Springer Nature ,1997
- Synthetic Studies on the IsomericN-Methyl Derivatives ofC-RibavirinNucleosides and Nucleotides, 1991
- Synthesis and evaluation of 5-amino-1-.beta.-D-ribofuranosyl-1,2,4-triazole-3-carboxamidine and certain related nucleosides as inhibitors of purine nucleoside phosphorylaseJournal of Medicinal Chemistry, 1988
- Synthesis of C-nucleosides by ring transformation of 1,3-oxazine derivatives.CHEMICAL & PHARMACEUTICAL BULLETIN, 1985
- A novel precursor for the synthesis of C-nucleoside analogs. Synthesis of the C-nucleoside analogs of ribavirin, bredinin, and related compoundsThe Journal of Organic Chemistry, 1980
- Synthesis of C-nucleosides. Part 14. 5(3)-Glycosyl-1,2,4-triazole-3(5) carboxamides as analogues of ribavirinJournal of the Chemical Society, Perkin Transactions 1, 1976
- C-Glycosyl nucleosides. I. Synthesis of pseudouridine and related compoundsThe Journal of Organic Chemistry, 1971
- C-nucleosides: aspects of chemistry and mode of actionPublished by Walter de Gruyter GmbH ,1971