The Controlled Stereospecific Reduction of Cyclopentenyl Cytosine (CPE-C) to Carbodine and Isocarbodine

Pamela L. Russ Laboratory of Medicinal Chemistry, DTP, DCT, National Cancer Institute, NIH, Bethesda, Maryland, 20892

Lajos Hegedus Laboratory of Medicinal Chemistry, DTP, DCT, National Cancer Institute, NIH, Bethesda, Maryland, 20892

James A. Kelley Laboratory of Medicinal Chemistry, DTP, DCT, National Cancer Institute, NIH, Bethesda, Maryland, 20892

Joseph J. Barchi Jr. Laboratory of Medicinal Chemistry, DTP, DCT, National Cancer Institute, NIH, Bethesda, Maryland, 20892

Victor E. Marquez Laboratory of Medicinal Chemistry, DTP, DCT, National Cancer Institute, NIH, Bethesda, Maryland, 20892

Abstract

The preferential cis-addition of hydrogen to either face of the carbocyclic double bond of enantiomerically pure cyclopentenyl cytosine (1) was achieved. The resulting saturated carbocyclic nucleosides carbodine (2) and isocarbodine (3) were evaluated against human influenza virus. Carbodine showed the greater potency against this virus but the activity of isocarbodine was still substantial.

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The Controlled Stereospecific Reduction of Cyclopentenyl Cytosine (CPE-C) to Carbodine and Isocarbodine

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The Controlled Stereospecific Reduction of Cyclopentenyl Cytosine (CPE-C) to Carbodine and Isocarbodine

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