5-Alkyloxymethyl Derivatives of 2ʹ-Deoxyuridine Bearing 2,4-Dinitrophenyl and Dansyl Groups: Synthesis and Antibacterial Activity

• Published in: Russian journal of bioorganic chemistry Vol. 49; no. Suppl 1; pp. S1 - S7
• Main Authors: Makarov, D. A., Oskolsky, I. A., Jasko, M. V., Solyev, P. N., Vasilyeva, B. F., Demiankova, M. V., Efremenkova, O. V., Kochetkov, S. N., Alexandrova, L. A.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-12-2023; Springer Nature B.V
• Subjects: Ammonia; Aqueous solutions; Biochemistry; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; Esters; Glycine; Life Sciences; Organic Chemistry; 5-dimethylaminonaphthalene-1-sulfonyl groups; antibacterial activity; nucleosides; bromosuccinimide; dinitrophenyl; condensation; azobisisobutyronitrile; hydroxysuccinimide
• ISSN: 1068-1620; 1608-330X
• DOI: 10.1134/S1068162023080010

Condensation of 3ʹ,5ʹ-di-
O
-acetyl-5-bromomethyl-2ʹ-deoxyuridine with 6-trifluoroacetylaminohexan1-ol yielded 5-(6-trifluoroacetylaminohexyl-1-oxymethyl)-3ʹ,5ʹ-di-
O
-acetyl-2ʹ-deoxyuridine. Its deblocking with an aqueous alcoholic solution of ammonia gave 5-(6-aminohexyl-1-oxymethyl)-2ʹ-deoxyuridine, and condensation with triazole and 2-chlorophenyl phosphorodichloridate followed by treatment with an aqueous solution of ammonia led to the formation of 5-(6-aminohexyl-1-oxymethyl)-2ʹ-deoxycytidine. The interaction of the obtained compounds with 2,4-dinitrofluorobenzene or
N
-hydroxysuccinimide esters of
N
-2,4-dinitrophenylaminohexanoic acid or 5-dimethylaminonaphthalene-1-sulfonyl glycine was used to synthesize DNP- and DNS-derivatives of 2ʹ-deoxyuridine as well as 5-(6-DNP-aminohexanoylaminohexyl-1-oxymethyl)-2ʹ-deoxycytidine. DNP derivatives of 2ʹ-deoxyuridine were shown to inhibit the growth of
Micrococcus luteus.