Structural peculiarities of 6-azacytosine and its derivatives imply intramolecular H-bonds

Samijlenko, S. P.; Alexeeva, I. V.; Palchykivs’ka, L.H; Kondratyuk, I. V.; Stepanyugin, A. V.; Shalamay, A. S.; Hovorun, Dmytro М.

doi:10.1016/s0022-2860(98)00749-2

Cited by 17 publications

(8 citation statements)

References 18 publications

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“…It is assumed that one of the NH 2 -group protons is involved in intramolecular hydrogen binding to the nitrogen atom N -4. [20] This interpretation is consistent with quantum-chemical [18] (e) NaIO 4 , then NaBH 4 . [19] characteristics of 6-azacytidine.…”

Section: Chemistrysupporting

confidence: 82%

Synthesis and Comparative Study of Anti-Adenoviral Activity of 6-Azacytidine and Its Analogues

Alexeeva

Nosach

Palchykovska

et al. 2015

Nucleosides, Nucleotides and Nucleic Acids

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This paper presents the results of synthesis and study of cytotoxicity and the anti-adenoviral activity of new N4-derivatives of 6-azacytidine and its α-L-glycopyranosyl analogues obtained by the simplified one-pot version of the silyl condensation method. The resulting acylated 4-methylmercapto-1,2,4-triazin-3(2Н)-one glycosides then underwent the amination and/or ammonolysis to provide 6-azacytidine glycoside analogues (2-6, 12, 15, 17) and compounds with modifications at both base and sugar fragments (11, 15). The evaluation of cytotoxicity and antiviral activity of new compounds against AdV5 showed high selectivity indexes for N4-methyl-6-azacytidine (2) and N,O-tetraacetyl-6-azacytidine (8). High anti-adenoviral activity of N4-methyl-6-azacytidine as well as very low cytotoxicity may suggest its further investigation as potential compound for the therapy of AdV infection.

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Section: Chemistrysupporting

confidence: 82%

Synthesis and Comparative Study of Anti-Adenoviral Activity of 6-Azacytidine and Its Analogues

Alexeeva

Nosach

Palchykovska

et al. 2015

Nucleosides, Nucleotides and Nucleic Acids

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“…We believe the latter to be due to N 4 -amino proton participation in an intramolecular hydrogen bond [14,15]. This may be the cause of decreasing biological activity of some N 4 -derivatives, as compared with 6-azaCyd (3c, 3g, 3m in Table 2).…”

Section: Some Characteristics Of Synthesized Nucleosidesmentioning

confidence: 99%

N4-amino-acid derivatives of 6-azacytidine: structure-activity relationship.

et al. 2000

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“…As such, 6-azacytosine was investigated in the past using different methods. [1][2][3][4][5][6] None of these studies concerned 6-azacytosine monomers in the gas phase or trapped in low-temperature inert matrices.…”

Section: Introductionmentioning

confidence: 99%

UV-induced transformations of matrix-isolated 6-azacytosine

Lapiński

Reva

Gerega

et al. 2018

The Journal of Chemical Physics

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UV-induced transformations were studied for monomers of 6-azacytosine isolated in low-temperature Ar matrices. In contrast to cytosine, where the amino-hydroxy () tautomer is the lowest-energy form, the amino-oxo () and imino-oxo () isomers of 6-azacytosine were found to be the most stable and most populated. Due to the high relative energy of the tautomer of 6-azacytosine, this form is not populated in low-temperature matrices after their formation and prior to any irradiation. Excitation of 6-azacytosine monomers with UV light from the 328-300 nm range led to structural transformations of and forms. The initially most populated tautomer was observed either to convert, in a phototautomeric reaction, into the product or to undergo photodecarbonylation to yield 4-amino-1,2,3-(2)-triazole. The relative efficiencies of the two processes depend on the wavelength and on the pulsed or continuous-wave character of the UV light used for excitation. For the tautomer of 6-azacytosine, the excitation with UV 328-300 nm light induced the photoconversion of the initially more populated anti isomer into the syn form. This transformation was found to be partially photoreversible.

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Structural peculiarities of 6-azacytosine and its derivatives imply intramolecular H-bonds

Cited by 17 publications

References 18 publications

Synthesis and Comparative Study of Anti-Adenoviral Activity of 6-Azacytidine and Its Analogues

Synthesis and Comparative Study of Anti-Adenoviral Activity of 6-Azacytidine and Its Analogues

N4-amino-acid derivatives of 6-azacytidine: structure-activity relationship.

UV-induced transformations of matrix-isolated 6-azacytosine

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