Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: a new class of antiviral acyclic nucleoside phosphonates.
A new class of acyclic nucleoside phosphonates, the 5-phosphono-pent-2-en-1-yl nucleosides and their hexadecyloxypropyl esters, were synthesized from butyn-1-ol. Only the hexadecyloxypropyl esters showed antiviral activity against herpes simplex virus type 1, in vitro. Hexadecyloxypropyl 1-(5-phosphono-pent-2-en-1-yl)-thymine was the most active and selective compound among the synthesized nucleotides with an EC50 value of 0.90 microM.
Choo
Hyunah
H
Department of Medicine, Division of Infectious Disease, University of California, San Diego, La Jolla, CA 92093-0676, USA.
Beadle
James R
JR
Chong
Youhoon
Y
Trahan
Julissa
J
Hostetler
Karl Y
KY
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D018259:Herpesvirus 1, Human / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D063065:Organophosphonates; D013941:Thymine
D000998:Antiviral Agents; D009705:Nucleosides; D063065:Organophosphonates; D013941:Thymine