Synthesis and antiherpetic activity of (Z)- and (E)-9-(3-phosphonomethoxyprop-1-en-yl)adenines

The isomeric (Z)- and (E)-9-(3-phosphonomethoxyprop-1-en-yl)adenines were synthesized. The stereoselectivity of double bond formation was studied by variation of sulfonyl groups. The resulting phosphonates exhibited a moderate antiherpetic activity in a culture of Vero cells infected with herpes simplex type 1 virus. The Z-isomer was shown to be a more effective inhibitor of virus reproduction in the case of both wild and acyclovir-resistant strains.