Aryl furano pyrimidines: The most potent and selective anti-VZV agents reported to date

Antiviral Research

Volumn 71, Issue 2-3 SPEC. ISS., 2006, Pages 149-153

  McGuigan, Christopher ^a   Balzarini, Jan ^b  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Bicyclic nucleoside analogue; Shingles; Varicella zoster virus

Indexed keywords

ANTIVIRUS AGENT; BICYCLIC NUCLEOSIDE DERIVATIVE; CARBOHYDRATE; FURANOPYRIMIDINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PYRIMIDINE DERIVATIVE; THYMIDINE KINASE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; CONTROLLED STUDY; DRUG SELECTIVITY; DRUG TARGETING; NONHUMAN; PRIORITY JOURNAL; SHORT SURVEY; STRUCTURE ACTIVITY RELATION; VARICELLA ZOSTER VIRUS;

ANTIVIRAL AGENTS; FURANS; HERPESVIRUS 3, HUMAN; HUMANS; MICROBIAL SENSITIVITY TESTS; PYRIMIDINE NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN HERPESVIRUS 3;

EID: 33747152824     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.antiviral.2006.04.001     Document Type: Short Survey

References (27)

1. Andrei G., Sienaert R., McGuigan C., De Clercq E., Balzarini J., and Snoeck R. Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides. Antimicrob. Agents Chemother. 49 (2005) 1081-1086
2. Angell A., McGuigan C., Sevillano L.G., Snoeck R., Andrei G., De Clercq E., and Balzarini J. Bicyclic anti-VZV nucleosides: thieno analogues bearing an alkylphenyl side chain have reduced antiviral activity. BioOrg. Med. Chem. Lett. 14 (2004) 2397-2399
3. Balzarini J., Sienaert R., Liekens S., Van Kuilenburg A., Carangio A., Esnouf R., De Clercq E., and McGuigan C. Lack of susceptibility of the highly potent inhibitors of varicella-zoster virus, bicyclic nucleoside analogues (BCNAs), to the catabolic action of thymidine phosphorylase and dihydropyrimidine dehydrogenase. Mol. Pharmacol. 61 (2002) 1140-1145
4. Balzarini J., and McGuigan C. Chemotherapy of varicella-zoster virus by a novel class of highly specific anti-VZV bicyclic pyrimidine nucleosides. Biochim. Biophys. Acta 1587 (2002) 287-295
5. Bidet O., McGuigan C., Snoeck R., Andrei G., De Clercq E., and Balzarini J. Non-nucleoside structures retain full anti-HCMV potency of the dideoxy furanopyrimidine family. Antivir. Chem. Chemother. 15 (2004) 329-332
6. Brancale A., Srinivasan S., McGuigan C., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Synthesis and anti-varicella zoster virus activity of some novel bicyclic nucleoside inhibitors: effect of enhanced aqueous solubility. Antivir. Chem Chemother. 11 (2000) 383-393
7. Brancale A., McGuigan C., Algain B., Savy P., Benhida R., Fourrey R.-L., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Bicyclic anti-VZV nucleosides: thieno analogues retain full antiviral activity. BioOrg. Med. Chem. Lett. 11 (2001) 2507-2510
8. Crisp G.T., and Flynn B.L. Palladium-catalyzed coupling of terminal alkynes with 5-(trifluorometh anesulfonyloxy) pyrimidine. J. Org. Chem. 58 (1993) 6114-6133
9. Kumar R., Knaus E.E., and Wiebe L.I. Synthesis and biological evaluation of 5-(1-alkoxy-2-haloethyl)-2′-deoxyuridines and related uracil analogs. Heterocycl. Chem. 28 (1991) 1917-1925
10. Kumar R., Wiebe L.I., and Knaus E.E. Synthesis of 5-(1-azi-dovinyl) and 5-[2-(1-azi-dovinyl) and 5-[2-(1-azirinyl)] analogs of 2′-deoxyuridine. Can. J. Chem. 74 (1996) 1609-1615
11. Luoni G., McGuigan C., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Bicyclic nucleoside inhibitors of varicella-zoster virus: 5-chloro and 3-chloro derivatives. Nucleos. Nucleot. Nucl. Acids 22 (2003) 931-933
12. Luoni G., McGuigan C., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Bicyclic nucleoside inhibitors of varicella-zoster virus modified on the sugar moiety: 3′ and 5′ derivatives. Antivir. Chem. Chemother. 15 (2004) 333-341
13. Luoni G., McGuigan C., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Bicyclic nucleoside inhibitors of varicella-zoster virus: the effect of branching in the p-alkylphenyl side-chain. BioOrg. Med. Chem. Lett. 15 (2005) 3791-3796
14. McGuigan C., Yarnold C.J., Jones G., Velázquez S., Barucki H., Brancale A., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Potent and selective inhibition of varicella-zoster virus (VZV) by nucleoside analogues with an unusual bicyclic base. J. Med. Chem. 42 (1999) 4479-4484
15. McGuigan C., Barucki H., Blewett S., Carangio A., Erichsen J.T., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Highly potent and selective inhibition of varicella-zoster virus by bicyclic furo pyrimidine nucleosides bearing an aryl side chain. J. Med. Chem. 43 (2000) 4993-4997
16. McGuigan C., Barucki H., Brancale A., Blewett S., Carangio A., Jones G., Pathirana R., Srinivasan S., Velázquez S., Yarnold C.J., Alvarez R., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Fluorescent bicyclic furo pyrimidine deoxynucleoside analogues as potent and selective inhibitors of VZV and potential future drugs for the treatment of chickenpox and shingles. Drugs Future 25 (2000) 1151-1161
17. McGuigan C., Pathirana R.N., Jones G., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Anti-varicella-zoster virus bicyclic nucleosides: replacement of furo by pyrro base reduces antiviral potency. Antivir. Chem. Chemother. 11 (2000) 343-348
18. 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 A., Snoeck R., De Clercq E., and Balzarini J. Furano pyrimidines as novel potent and selective anti-VZV agents. Antivir. Chem. Chemother. 12 (2001) 77-89
19. McGuigan C., Blewett S., Siccardi D., Erichsen J.T., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Alkyloxyphenyl furano pyrimidines as potent and selective anti-VZV agents with enhanced water solubility. Antivir. Chem. Chemother. 13 (2002) 91-99
20. McGuigan C., Jukes A., Blewett S., Barucki H., Erichsen J.T., Andrei G., Snoeck R., De Clercq E., and Balzarini J. Halophenyl furanopyrimidines as potent and selective anti-VZV Agents. Antivir. Chem. Chemother. 14 (2003) 165-170
21. McGuigan C., Carangio A., Snoeck R., Andrei G., De Clercq E., and Balzarini J. Synthesis and antiviral evaluation of some 3′-fluoro bicyclic nucleoside analogues. Nucleos. Nucleot. 23 (2004) 1-5
22. McGuigan C., Pathirana R.N., Snoeck R., Andrei G., De Clercq E., and Balzarini J. Discovery of a new family of inhibitors of human cytomegalovirus (HCMV) based upon lipophilic alkyl furano pyrimidine dideoxy nucleosides: action via a novel non-nucleosidic mechanism. J. Med. Chem. 47 (2004) 1847-1851
23. Robins M.J., and Barr P.J. Nucleic-Acid related-compounds. 31. Smooth and efficient palladium copper catalyzed coupling of terminal alkynes with 5-iodouracil nucleosides. Tetrahedron Lett. 22 (1981) 421-424
24. Robins M.J., and Barr P.J. Nucleic-acid related-compounds. 39. Efficient conversion of 5-iodo to 5-alkynyl and derived 5-substituted uracil bases and nucleosides. J. Org. Chem. 48 (1983) 1854-1862
25. Robins M.J., Vinayak R.S., and Wood S.G. Nucleic-acid related-compounds. 59. Solvent, not paddadium oxidation-state, is the primary determinant for successful coupling of terminal alkynes with iodo nucleosides. Tetrahedron Lett. 31 (1990) 3731-3734
26. Sienaert R., Naesens L., Brancale A., De Clercq E., McGuigan C., and Balzarini J. Specific recognition of the bicyclic pyrimidine nucleoside analogs, a new class of highly potent and selective inhibitors of varicella-zoster virus (VZV), by the VZV-encoded thymidine kinase. Mol. Pharmacol. 61 (2002) 249-254
27. Sienaert R., Andrei G., Snoeck R., De Clercq E., McGuigan C., and Balzarini J. Inactivity of the bicyclic pyrimidine nucleoside analogues against simian varicella virus (SVV) does not correlate with their substrate activity for SVV-encoded thymidine kinase. Biochem. Biophys. Res. Commun. 315 (2004) 877-883