Synthesis and biological activity of modified (2'-5')triadenylates containing 2'-terminal 2',3'-dideoxy-3'-fluoroadenosine derivatives

Article abstract of DOI:10.1002/hlca.19980810538

Some new (2'-5')triadenylates 13-16, containing at the 2'-terminal end 3'-fluoro-2',3'-dideoxyadenosine derivatives, have been synthesized by the phosphotriester method. The selectively blocked nucleosides 2, 4, 5, and 7 were synthesized from the corresponding unprotected 'nucleosides 1, 3, and 6. The synthesized trimers 13 and 14 were 4- and 8-fold, respectively, more stable towards phosphodiesterase from Crotalus durissus than the natural trimer 17. In comparison to trimer 17 the new compounds 13-15 inhibit HIV-1 reverse transcriptase (RT) activity, and 15 and 16 the HIV-1 induced syncytia formation 2-3 fold whereas none of 13-16 can improve RNase L activity.