Based on the potent anti-HIV activity of l-2′,3′-dideoxycytidine (l-ddC), l-2′,3′-dideoxy-4′-selenonucleosides (l-4′-Se-ddNs) have been synthesized from natural chiral template, l-glutamic acid, using Pummerer-type condensation as a key step. All synthesized compounds were assayed for anti-HIV-1 activity, but none of them did show any significant antiviral activity up to 100 μM, probably due to conformational differences between l-ddC and l-4′-Se-ddC, induced by the bulky selenium atom, which might play an important role in phosphorylation by cellular kinase.
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Acknowledgements This research was supported by grants from Mid-career Research Program (2016R1A2B3010164) and Basic Science Research Program (2018R1D1A1A02085459) of the National Research Foundation (NRF), Korea. Antiviral assay by C.-K. Lee (KRICT) is greatly appreciated.
© 2019, The Pharmaceutical Society of Korea.
- Pummerer-type condensation