Synthesis of new 1,2,3-triazolo-nucleoside analogues with 2-propargylamino pyrimidines via click reactions

Ay E.

Nucleosides, Nucleotides and Nucleic Acids, cilt.42, sa.3, ss.191-205, 2023 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 42 Sayı: 3
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1080/15257770.2022.2118317
  • Dergi Adı: Nucleosides, Nucleotides and Nucleic Acids
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, BIOSIS, Chemical Abstracts Core, Chimica, MEDLINE
  • Sayfa Sayıları: ss.191-205
  • Anahtar Kelimeler: Click reaction, nucleoside analogues, 2-propargylamino pyrimidine, 1, 2, 3-triazolo-nucleoside, 1, 2, 3-triazole
  • Manisa Celal Bayar Üniversitesi Adresli: Evet

Özet

In this study, it was reported that twelve nucleoside analogues were synthesized by click reactions. The reactions were carried out between the azide derivatives of D-glucopyranose, D-galactopyranose, D-ribofuranose and 2-propargylamino pyrimidine derivatives (5 and 7) that are synthesized via a different route for the first time. In the first step, N-propargyl guanidine was obtained with the reaction of 1H-pyrazole-1-carboxamidine hydrochloride and propargyl amine, then condensation of N-propargyl guanidine and β-diketone (4 and 6) resulted in 2-propargylamino pyrimidines (5 and 7) for the first time in good yields (85%). Finally, click reactions were performed with azidosugars (8a-8f) and 2-propargylamino pyrimidine derivatives and produced twelve new nucleoside analogues in good yields. (9a-9f, 10a-10f, 65-73% yields). The chemical structures of the new derivatives were elucidated spectroscopic techniques, such as FT-IR, 1H NMR, 19F NMR, 13C NMR and TOF-ESI-MS.