Efficient Synthesis and Antimicrobial Evaluation of Acyclic Pyrimidine Nucleosides and Their Sulfanyl Analogs

A facile synthetic approach has been proposed for a new series of uracil acyclic nucleosides and their sulfanyl analogs via reaction of pyrimidine derivatives with a number of acyclic halides such as 4-bromobutyl acetate, 2-(bromomethoxy)ethyl acetate, 3-chloropropan-1-ol, epichlorohydrin, allyl bro...

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 58; no. 3; pp. 385 - 393
Main Authors Alkabli, J., Moustafa, A. H.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 01.03.2022
Springer Nature B.V
Subjects
Ampicillin
Analogs
Chemistry
Chemistry and Materials Science
E coli
Epichlorohydrin
Ethyl acetate
Halides
Nucleosides
Organic Chemistry
Potassium carbonate
Pseudomonas aeruginosa
Room temperature
Uracil
antibacterial activity
sulfanyl analogs
pyrimidine-5-carbonitrile
acyclic nucleoside
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Summary:A facile synthetic approach has been proposed for a new series of uracil acyclic nucleosides and their sulfanyl analogs via reaction of pyrimidine derivatives with a number of acyclic halides such as 4-bromobutyl acetate, 2-(bromomethoxy)ethyl acetate, 3-chloropropan-1-ol, epichlorohydrin, allyl bromide, and propargyl bromide). The desired products were obtained in good yields (68–90%) at room temperature in the presence of potassium carbonate. Some of the synthesized compounds showed significant antibacterial activity against Bacillus cereus , Staphylococcus aureus , Escherichia coli , and Pseudomonas aeruginosa (inhibition zone diameter 19–29 mm compared to 21–26 mm for Ampicillin taken as reference drug).
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428022030186