Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: A new class of antiviral acyclic nucleoside phosphonates

…, JR Beadle, Y Chong, J Trahan, KY Hostetler

Index: Choo, Hyunah; Beadle, James R.; Chong, Youhoon; Trahan, Julissa; Hostetler, Karl Y. Bioorganic and Medicinal Chemistry, 2007 , vol. 15, # 4 p. 1771 - 1779

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Citation Number: 27

Abstract

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 ...