Chemistry and Anti-HIV Activity of 2′-β-Fluoro-2′,3′-dideoxyguanosine

Harry Ford Jr. Laboratory of Medicinal Chemistry, Developmental Therapeutics Program, 9000 Rockville Pike, Building 37, Room 5C-02, Bethesda, MD, 20892

John S. Driscoll Laboratory of Medicinal Chemistry, Developmental Therapeutics Program, 9000 Rockville Pike, Building 37, Room 5C-02, Bethesda, MD, 20892

Maqbool Siddiqui Laboratory of Medicinal Chemistry, Developmental Therapeutics Program, 9000 Rockville Pike, Building 37, Room 5C-02, Bethesda, MD, 20892

James A. Kelley Laboratory of Medicinal Chemistry, Developmental Therapeutics Program, 9000 Rockville Pike, Building 37, Room 5C-02, Bethesda, MD, 20892

Hioraki Mitsuya Experimental Retrovirology Section, Medicine Branch, Clinical Oncology Program, Division of Cancer Treatment, National Cancer Institute, National Institutes of Health, 9000 Rockville Pike, Building 37, Room 5C-02, Bethesda, MD, 20892

Takuma Shirasaka Experimental Retrovirology Section, Medicine Branch, Clinical Oncology Program, Division of Cancer Treatment, National Cancer Institute, National Institutes of Health, 9000 Rockville Pike, Building 37, Room 5C-02, Bethesda, MD, 20892

David G. Johns Laboratory of Medicinal Chemistry, Developmental Therapeutics Program, 9000 Rockville Pike, Building 37, Room 5C-02, Bethesda, MD, 20892

Victor E. Marquez Laboratory of Medicinal Chemistry, Developmental Therapeutics Program, 9000 Rockville Pike, Building 37, Room 5C-02, Bethesda, MD, 20892

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Abstract

The 2′-β-fluoro analogue of 2′,3′-dideoxyguanosine has been prepared by two synthetic routes. This compound and two analogues have anti-HIV activity in at least two of three host cell systems used (ATH8, CEM, PBL). These compounds, as well as their ddGuo parents, have been characterized with regard to their acid-stabilities, octanol-water partition coefficients, and enzyme substrate properties for adenosine deaminase and purine nucleoside phosphorylase. F-ddGuo analogues are less potent but more stable than their non-fluorinated parent compounds.

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Chemistry and Anti-HIV Activity of 2′-β-Fluoro-2′,3′-dideoxyguanosine

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Chemistry and Anti-HIV Activity of 2′-β-Fluoro-2′,3′-dideoxyguanosine

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