Alkyloxyphenyl furano pyrimidines as potent and selective anti-VZV agents with enhanced water solubility

Antiviral Chemistry and Chemotherapy

Volumn 13, Issue 2, 2002, Pages 91-99

  McGuigan, Christopher ^a   Blewett, Sally ^a   Siccardi, Dario ^a   Erichsen, Jonathan T ^b   Andrei, Graciela ^c   Snoek, Robert ^c   De Clercq, Erik ^c   Balzarini, Jan ^c  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Furanopyrimidines; Nucleosides; VZV

Indexed keywords

3 (2' DEOXY BETA DEXTRO RIBOFURANOSYL) 6 (4 N ETHOXYPHENYL) 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; 3 (2' DEOXY BETA DEXTRO RIBOFURANOSYL) 6 (4 N HEPTOXYPHENYL) 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; 3 (2' DEOXY BETA DEXTRO RIBOFURANOSYL) 6 (4 N HEXOXYPHENYL) 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; 3 (2' DEOXY BETA DEXTRO RIBOFURANOSYL) 6 (4 N METHOXYPHENYL) 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; 3 (2' DEOXY BETA DEXTRO RIBOFURANOSYL) 6 (4 N PENTOXYPHENYL) 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; 3 (2' DEOXY BETA DEXTRO RIBOFURANOSYL) 6 (4 N PROPOXYPHENYL) 2,3 DIHYDROFURO[2,3 D]PYRIMIDIN 2 ONE; ACICLOVIR; ANTIVIRUS AGENT; FURAN DERIVATIVE; FURANOPYRIMIDINE DERIVATIVE; PHENOL DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYCLIZATION; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SOLUBILITY; DRUG SYNTHESIS; EMBRYO; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HYDROPHILICITY; LIPOPHILICITY; LUNG FIBROBLAST; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; VACCINIA VIRUS; VARICELLA ZOSTER VIRUS; VIRUS INHIBITION;

EID: 0013163559     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632020201300203     Document Type: Article

References (8)

1. Brancale A, McGuigan C, Andrei G, Snoeck R, De Clercq E & Balzarini J (2000a) Bicyclic nucleoside inhibitors of varicella-zoster virus (VZV): the effect of a terminal halogen substitution in the side chain. Bioorganic & Medicinal Chemistry Letters 10:1215-1217.
2. Brancale A, Srinivasan S, McGuigan C, Andrei G, Snoeck R, De Clercq E & Balzarini J (2000b) Synthesis and anti-VZV activity of some novel bicyclic nucleoside inhibitors: Ether and glycol analogues with enhanced water solubility have reduced antiviral potency. Antiviral Chemistry & Chemotherapy 11:383-393.
3. De Clercq E, Descamps J, De Somer P, Barr PJ, Jones AS & Walker RT (1979) (E)-5-(2-Bromovinyl)-2′-deoxyuridine. A potent and selective antiherpes agent. Proceedings of the National Academy of Sciences USA 76:2947-2951.
4. De Clercq E, Holy A, Rosenberg I, Sakuma T, Balzarini J & Maudgal PC (1986) A novel selective broad-spectrum anti-DNA virus agent. Nature 324:464-467.
5. McGuigan C, Yarnold CJ, Jones G, Velázquez S, Barucki H, Brancale A, Andrei G, Snoeck R, De Clercq E & Balzarini J (1999) Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base. Journal of Medicinal Chemistry 42:4479-4484.
6. McGuigan C, Barucki H, Blewett S, Erichsen TT, Carangio A, Andrei G, Snoeck R, De Clercq E & Balzarini J (2000) Highly potent and selective inhibition of varicella-zoster virus (VZV) by bicyclic furo pyrimidine nucleosides bearing an aryl side-chain. Journal of Medicinal Chemistry 43:4993-4997.
7. McGuigan C, Brancale A, Barucki H, Srinivasan S, Jones G, Pathirana R, Carangio A, Blewett S, Luoni G, Bidet O, Jukes A, Jarvis C, Andrei G, Snoeck R, De Clercq E & Balzarini J (2001) Furano pyrimidines as novel potent and selective anti-VZV agents. Antiviral Chemistry & Chemotherapy 12:77-89.
8. Srinivasan S, McGuigan C, Andrei G, Snoeck R, De Clercq E & Balzarini J (2001) Bicyclic nuceoside inhibitors of varicella-zoster virus (VZV): the effect of terminal unsaturation in the side-chain. Bioorganic & Medicinal Chemistry Letters 11:391-393.