6-Methyl-5-azacytidine - Synthesis, conformational properties and biological activity. A comparison of molecular conformation with 5- azacytidine

Article abstract of DOI:10.1080/07328319708002528

The title compound was prepared by the isocyanate procedure and the trimethylsilyl method. The measurement of ¹H NMR spectrum of 6-methyl-5- azacytidine (1) revealed a preference of γ(t) (46%) rotamer around C(5')- C(4') bond, a predominance of N conformation of the ribose ring (K(eq) 0.33) and a preference of syn conformation around the C-N glycosyl bond. An analogous measurement of 5-azacytidine has shown a preference of γ⁺ (60%) rotamer around the C(5')-C(4') bond, a predominance of N conformation of the fibose ring (K(eq) 0.41) and a preference of anti conformation around the C- N glycosyl bond 6-Methyl-5-azacytidine (1) inhibits the growth of bacteria E coli to the extent of 85% at 4000 μM concentration and the growth of LoVo/L, a human colon carcinoma cell line, to the extent of 30% at 100 μM concentration but did not inhibit L1210 cells at ≤ 100 μM concentration 6- Methyl-5-azacytidine (1) exhibited no in vitro antiviral activity at ≤ 1 μM concentration.

Full text of DOI:10.1080/07328319708002528

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6-Methyl-5-Azacytidine-Synthesis,
Conformational Properties and Biological
Activity. A Comparison of Molecular
Conformation with 5-Azacytidine
Naeem B. Hanna a , Jaroslav Zajíček a & Alois Pískala a
a Institute of Organic Chemistry and Biochemistry, Academy of
Sciences of the Czech Republic , 166 10 Prague 6, The Czech
Republic
Published online: 20 Aug 2006.
To cite this article: Naeem B. Hanna , Jaroslav Zajíček & Alois Pískala (1997) 6-Methyl-5-Azacytidine-
Synthesis, Conformational Properties and Biological Activity. A Comparison of Molecular Conformation
with 5-Azacytidine, Nucleosides and Nucleotides, 16:1-2, 129-144, DOI: 10.1080/07328319708002528
To link to this article: http://dx.doi.org/10.1080/07328319708002528
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