3 years ago
Synthesis, conformational study and antiviral activity of l-like neplanocin derivatives
The l -like enantiomer of 9-(trans-2′, trans-3′-dihydroxycyclopent-4′-enyl)-3-deazaadenine (DHCDA) (1 ), its 3-deaza-3-bromo derivative (3 ), and the conformational restricted methanocarba (MC) nucleoside analogues (2 and 4 ) were synthesized. X-ray crystal structures showed the L isomer MC analogue 4 adopts a similar North-like locked conformation as conventional D-MC nucleosides, while the DHCDA analogue 3 preferred south-like conformer. Compounds 1 and 4 showed potent antiviral activity against norovirus, while compound 2 and 3 were less potent or inactive. The conformational behavior of “sugar” puckering (north/south) and nucleobase orientation (syn /anti) may contribute to the antiviral activity differences. For compound 3 , antiviral activity was also found against Ebola virus.
Publisher URL: www.sciencedirect.com/science
DOI: S0960894X17307977
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