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

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

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-deoxyuridi...

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Bibliographic Details
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
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Summary: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.
ISSN:1068-1620
1608-330X
DOI:10.1134/S1068162023080010