Bicyclic nucleoside inhibitors of varicella-zoster virus (VZV): The effect of a terminal halogen substitution in the side-chain

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 11, 2000, Pages 1215-1217

  Brancale, Andrea ^a   McGuigan, Christopher ^a   Andrei, Graciela ^b   Snoeck, Robert ^b   De Clercq, Erik ^b   Balzarini, Jan ^b  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ACICLOVIR; HALOGEN; NUCLEOSIDE ANALOG;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL MODIFICATION; DRUG DESIGN; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS; VARICELLA ZOSTER VIRUS; VIRUS INFECTION;

ANTIVIRAL AGENTS; HALOGENS; HERPESVIRUS 3, HUMAN; NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA; DNA VIRUSES; HUMAN HERPESVIRUS 3;

EID: 0034608469     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00193-1     Document Type: Article

References (9)

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4. 4, filtered and the solvent removed in vacuo, yielding to the product 2b as a colourless oil in quantitative yield.
5. Danishefsky S., Berman E.M., Ciufolini M., Etheredge S.J., Segmuller B.E. J. Am. Chem. Soc. 107:1985;3891.
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7. - form) was added and the mixture was stirred for 30 min. The resin was then filtered, washed with methanol and the combined filtrate was evaporated to dryness. The crude product was purified by silica gel column chromatography using ethyl acetate as eluent. The appropriate fractions were combined and the solvent removed in vacuo to yield 4b as a white solid (540 mg, 58% yield).
8. Preparation of 5b: to a stirred solution of 4b (200 mg) in methanol:triethylamine (7:3) (20 mL), at room temperature under a nitrogen atmosphere, was added copper (I) iodide (20 mg). The reaction mixture was then heated to reflux and stirred for 4 h. The solvent was removed in vacuo and the crude product purified by silica column chromatography, using an initial eluent of ethyl acetate, followed by an eluent of ethyl acetate:methanol (9:1). The appropriate fractions were combined and the solvent removed in vacuo yielding the pure product 5b (140 mg, 70% yield).
9. 5Na requires 435.1663).