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Trends in Applied Sciences Research
  Year: 2011 | Volume: 6 | Issue: 1 | Page No.: 19-33
DOI: 10.3923/tasr.2011.19.33
 
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Regioselective Glycosylation: Synthesis, Characterization and Biological Evaluation of New Acyclo C-nucleosides Bearing 5-(substituted) -1,3,4-oxadiazole-2-thione, 5-(substituted) -4-amino-1,2,4-triazole-3-thiol and 5-(substituted) -1,2,4-triazole-3-thiones Moieties

Mohamed Belkadi and Adil A. Othman

Abstract:
A several carboxylic acid derivatives 1a-b were used as starting materials to prepare an open chain C-nucleosides analogue, which exhibit distinguished antitumor and antiviral activities. Consequently, various analogues of C-nucleosides analogues have been synthesized to improve its chemotherapeutic index, including modification of the sugar ring as well as modification of the heterocyclic ring. In this study, subsequently after esterification, the compounds 2a-b were converted to acid hydrazides 3a-b by treatment with hydrazine hydrate. Moreover, the reaction of hydrazides with carbon disulfide in the presence of KOH afforded the 5-(5'-hydroxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl) -3H-[1,3,4] oxadia zole -2-thione 4a-b. In parallel, the treatment of same hydrazides with ammonium thiocyanate in dry benzene under reflux produced [5’- (3-mercapto-1H-1,2,4-triazol-5-yl)-2,2,2’,2’-tetra methyl-4,4’-bi-1,3-dioxol-5-yl]methanol 9a-b. The intermediates and the final products were fully characterized with IR, MS, 1H-NMR and elemental analysis all synthesized compounds were found to have appreciable effects in antibacterial activity against some pathogenic bacteria that causes infectious diseases.
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How to cite this article:

Mohamed Belkadi and Adil A. Othman, 2011. Regioselective Glycosylation: Synthesis, Characterization and Biological Evaluation of New Acyclo C-nucleosides Bearing 5-(substituted) -1,3,4-oxadiazole-2-thione, 5-(substituted) -4-amino-1,2,4-triazole-3-thiol and 5-(substituted) -1,2,4-triazole-3-thiones Moieties. Trends in Applied Sciences Research, 6: 19-33.

DOI: 10.3923/tasr.2011.19.33

URL: https://scialert.net/abstract/?doi=tasr.2011.19.33

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