Synthesis and biological evaluation of carboacyclic nucleosides with (Z) and (E)-9-[4,4-bis(hydroxymethyl)]-2-butenyl side chain

Ye Tang; Ramaiah Muthyala; Robert Vince

doi:10.1016/j.bmc.2006.05.029

Synthesis and biological evaluation of carboacyclic nucleosides with (Z) and (E)-9-[4,4-bis(hydroxymethyl)]-2-butenyl side chain

Bioorg Med Chem. 2006 Sep 1;14(17):5866-75. doi: 10.1016/j.bmc.2006.05.029. Epub 2006 Jun 8.

Authors

Ye Tang¹, Ramaiah Muthyala, Robert Vince

Affiliation

¹ Center for Drug Design, Academic Health Center and Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis, MN 55455, USA.

PMID: 16759867
DOI: 10.1016/j.bmc.2006.05.029

Abstract

A series of carboacyclic nucleosides with (Z) and (E)-9-[4,4-bis(hydroxy-methyl)]-2-butenyl side chains were synthesized as ring open analogs of cyclohexene nucleosides 1 and bioisosteres of ganciclovir 3. The (E)-isomers were obtained to compare the side chain geometry effect on antiviral activity.

MeSH terms

Animals
Antiviral Agents / chemical synthesis*
Antiviral Agents / chemistry
Antiviral Agents / pharmacology*
Chlorocebus aethiops
Ganciclovir / chemistry
Ganciclovir / pharmacology
Herpesvirus 1, Human / drug effects
Herpesvirus 2, Human / drug effects
Molecular Structure
Purine Nucleosides / chemical synthesis
Purine Nucleosides / chemistry*
Purine Nucleosides / pharmacology*
Vero Cells

Substances

Antiviral Agents
Purine Nucleosides
Ganciclovir