Novel 3′-[4-fluoroaryl-(1,2,3-triazol-1-yl)]-3′-deoxythymidine analogues: Design, synthesis, characterization and their potential as anticancer agents

Abstract

Novel 3′-[4-fluoroaryl-(1,2,3-triazol-1-yl)]-3′-deoxythymidine analogues (7a-l) were developed by the Cu alkyne-azide cycloaddition (CuAAC) reaction. The obtained lead compounds were confirmed by using ¹H NMR, ¹³C NMR, 2 D NMR, HRMS and their anticancer activities were screened against Huh-7 liver cancer cells and U87MG human glioblastoma cells. Among the synthesized fluorinated 1,2,3-triazolyl nucleosides, three compounds (7i, 7a-b) demonstrated promising anti-proliferative against Huh-7 and U87MG cell lines. Significantly, compound 7i has displayed remarkable promising anticancer activity with IC₅₀ value in the micromole range (22.41–24.92 µM) and (18.12–21.36 µM) against Huh-7 cancer cells and U87MG glioblastoma cells, respectively.

Keywords:

• 1,2,3-Triazole
• fluorinated 1,2,3-trizolyl nucleosides
• CuAAC reaction
• cytotoxity
• anticancer activity

Acknowledgments

The authors pay sincere thanks to Department of Chemistry, Institute of Integrated & Honors Studies (IIHS), Kurukshetra University, Kurukshetra, for providing laboratory facilities. SAIF, Panjab University, Chandigarh is thanked for recording the NMR and Mass spectra.

Disclosure statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Additional information

Funding

The authors are thankful to Council of Scientific and Industrial Research (CSIR), New Delhi, for awarding Fellowship (JRF) to Mr. Ankit.