One-pot click synthesis of 1,2,3-triazole-embedded unsaturated uracil derivatives and hybrids of 1,5- and 2,5-disubstituted tetrazoles and pyrimidines

• Published in: Tetrahedron letters Vol. 56; no. 10; pp. 1222 - 1228
• Main Authors: Krištafor, Svjetlana, Bistrović, Andrea, Plavec, Janez, Makuc, Damjan, Martinović, Tamara, Kraljević Pavelić, Sandra, Raić-Malić, Silvana
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 04.03.2015; Elsevier
• Subjects: 1,2,3-Triazoles; 1,5- and 2,5-disubstituted tetrazoles; Antitumor activity; Chemistry; Chemistry, Organic; Click chemistry; One-pot; Physical Sciences; Science & Technology; 1,2,3-Triazoles; One-pot; Antitumor activity; 1,5- and 2,5-disubstituted tetrazoles; Click chemistry; 1,5-and 2,5-disubstituted tetrazoles; DESIGN; ACID; AZIDES; ANALOGS; CATALYZED SYNTHESIS; NUCLEOTIDE; NUCLEOSIDE; 1,3-DIPOLAR CYCLOADDITION; BIOLOGICAL EVALUATION; CHEMISTRY
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2015.01.152

[Display omitted] Novel conformationally restricted pyrimidine derivatives with a 1,2,3-triazolyl scaffold bound via Z- and E-2-butenyl spacers were prepared by Cu(I)-catalyzed click chemistry via a one-pot, multi-step reaction under microwave irradiation, while 1,5- and 2,5-disubstituted tetrazoles were synthesized by convenient, environmentally friendly click synthesis and subsequently by N-alkylation of 5-substituted 1H-tetrazoles. Among all the tested compounds, the N-1,N-3-disubstituted olefinic uracil derivative showed the highest antiproliferative effects.