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A series of 2'-deoxy-4'-thioribo purine nucleosides was prepared by trans-N-deoxyribosylase-catalyzed reaction of 2'-deoxy-4'-thiouridine with a variety of purine bases. This synthetic procedure is an improvement over methods previously used to prepare purine 4'-thio nucleosides. The compounds were tested against hepatitis B virus (HBV), human cytomegalovirus (HCMV), herpes simplex virus (HSV-1 and HSV-2), varicella zoster virus (VZV), and human immunodeficiency virus (HIV-1). Cytotoxicity was determined in a number of cell lines. Several compounds were extremely potent against HBV and HCMV and had moderate to severe cytotoxicity in vitro. The lead compound from the series, 2-amino-6-(cyclopropylamino)purine 2'-deoxy-4'-thioriboside, was the most potent and selective agent against HCMV and HBV replication in vitro; however, this analogue was nephrotoxic when tested in vivo.
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N A Van Draanen, and
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N A Van Draanen, and
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Chemical biology & drug design,
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N A Van Draanen, and
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Nucleosides, nucleotides & nucleic acids,
N A Van Draanen, and
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G Szczech, and
G W Koszalka
September 1991,
Journal of medicinal chemistry,
N A Van Draanen, and
G A Freeman, and
S A Short, and
R Harvey, and
R Jansen, and
G Szczech, and
G W Koszalka
January 1999,
Nucleosides & nucleotides,
N A Van Draanen, and
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R Jansen, and
G Szczech, and
G W Koszalka
March 1999,
Bioorganic & medicinal chemistry,
N A Van Draanen, and
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G Szczech, and
G W Koszalka
July 2000,
Bioorganic & medicinal chemistry,
