The tetrahydrofuranylic derivatives of C6 substituted 3,5-dioxo- and 3,5-thioxo-1,2,4-triazines as a structural analogs of azapyrimidine nucleosides
DOI:
https://doi.org/10.7124/bc.000459Abstract
Influence of C6-aminoalkyl-, C6-mercaptoalkyl-substitutes of 3,5-dioxo- and 3,5-thioxo-derivatives 1,2,4-triazines on the process of tetrahydrofuranylation has been studied. This study was conducted in the conditions, similar to the one-step reaction of nucleic bases glycosylation. We discovered significant dependence of the regiospecifity of this reaction from electronic nature of substitutes in the 6-position.References
Vorbr?ggen H. Methods of Nucleoside Synthesis. Nucleoside Analogues. Chemistry, Biolody and Medical Application. Ed. R. T. Walker. New York: Plenum press, 1980. Vol. 26: 35-69.
Vorbruggen H, Benua B. Nucleoside Synthesis. XXIII. The One-Step. One-Pot-Reaction. Chem Ber. 1981. 114: 1280-5.
Alekseeva IV, Pal’chikovskaya LI, Shalamai AS, Ognyanik SS, Morgart NV, Petrusha NA. Synthesis of N1-substituted 6-azacytosines and their biological activity. Pharmaceutical Chemistry Journal. 1994;28(4):227–30.
Ognyanik SS, Tarnavsky SS, Kobylinskaya VI, Alekseeva IV, Shalamai AS. Glycosylation of 5-N-aminoacidic derivatives of 6-azauracyl and 2-thio-6-azauracyl. Ukr Khim Zh. 1988;54(10):1094-8.
Wierenga W, Skulnick HI. Investigations of the mechanism of nucleoside synthesis. I. 13C-NMR studies of dihydro--triazine-SnCl4 complexes. Tetrahedron Lett. 1979;20(38):3631–4.
Cristescu C. as-Triasin-Derivate, die moglieherweise therapeutische Wirkung besitzen, 15. Mitt.: Synthese von neuen blockierten 5-substituten 4-thio-6-azauridinen. Monatsh Chem. 1977; 108(6):1455-9.