Halay Erkan, Ay Emriye, Şalva Emine, Ay Kadir, Karayıldırım Tamer
a Scientific Analysis Technological Application and Research Center , Uşak University , Uşak , Turkey.
b Department of Food Technology, Şebinkarahisar School of Applied Sciences , Giresun University , Giresun , Turkey.
Nucleosides Nucleotides Nucleic Acids. 2017 Sep 2;36(9):598-619. doi: 10.1080/15257770.2017.1346258.
With the aim to create a library of compounds with potential bioactivities by combining special characteristics of two important groups such as nucleobases and carbohydrates, twenty 1,4-disubstituted-triazole nucleosides were synthesized in good yields (80-94%) using the copper catalyzed 'Click' reaction between azido-modified pento- or hexopyranoses and alkyne-bearing pyrimidine or purine nucleobases. Structural elucidation was made with the assistance of spectroscopic techniques such as FTIR, 1D-, 2D-NMR, and ESI-TOFMS. All the synthesized triazole nucleosides were evaluated for their cytotoxic activity against three human cancer cell lines (MDA-MB-231, Hep3B, PC-3) by using the MTT assay. Particularly, compounds 3a and 1b were identified as potential hits against Hep3B cell.
为了通过结合核碱基和碳水化合物这两个重要基团的特殊性质来创建一个具有潜在生物活性的化合物库，利用叠氮基修饰的戊糖或己糖与含炔基的嘧啶或嘌呤核碱基之间的铜催化“点击”反应，以良好的产率（80 - 94%）合成了20种1,4 - 二取代 - 三唑核苷。借助FTIR、一维和二维NMR以及ESI - TOFMS等光谱技术进行结构解析。通过MTT法评估了所有合成的三唑核苷对三种人类癌细胞系（MDA - MB - 231、Hep3B、PC - 3）的细胞毒性活性。特别地，化合物3a和1b被鉴定为对Hep3B细胞有潜在活性的化合物。
