Synthesis of novel 1, 2, 3-triazolyl nucleoside analogues bearing uracil, 6-methyluracil, 3, 6-dimethyluracil, thymine, and quinazoline-2, 4-dione moieties. Issue 47 (21st November 2019)

• Record Type: Journal Article
• Authors: Andreeva, Olga V.; Belenok, Maya G.; Saifina, Liliya F.; Shulaeva, Marina M.; Dobrynin, Alexey B.; Sharipova, Radmila R.; Voloshina, Alexandra D.; Saifina, Alina F.; Gubaidullin, Aidar T.; Khairutdinov, Bulat I.; Zuev, Yuriy F.; Semenov, Vyacheslav E.; Kataev, Vladimir E.
• Is Part Of: Tetrahedron letters. Volume 60:Issue 47(2019)
• Publication Date: 2019-11-21
• Subjects: Nucleoside analogues -- 1, 2, 3-Triazole -- Uracil -- Click chemistry; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151276
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A series of novel 1, 2, 3-triazolyl pyrimidine nucleoside analogues was synthesized. The pyrimidine moiety was connected to a triazolyl ring by a linker of variable length. The obtained compounds differ in the nature of pyrimidine moiety and the linker length. All obtained compounds were non-cytotoxic in relation to the normal human cell lines. Abstract: A series of novel 1, 2, 3-triazolyl nucleoside analogues was synthesized via the CuAAC reaction of N 1-alkynyl uracil, 6-methyluracil, 3, 6-dimethyl uracil, thymine and quinazolin-2, 4-dione with protected azido β- d -ribofuranose. The obtained compounds differ in both the nature of the pyrimidine-2, 4-dione fragment and the length of the polymethylene linker connecting it with the β- d -ribofuranosyl-1, 2, 3-triazol-4-yl moiety. The 1, 2, 3-triazolyl nucleoside analogues were evaluated for their cytotoxicity in vitro .