An efficient alternative route to 3,6-disubstituted-furo[2,3-d]pyrimidin-2- one analogues

Nucleosides, Nucleotides and Nucleic Acids

Volumn 24, Issue 10-12, 2005, Pages 1729-1743

  Janeba, Zlatko ^a,b   Maklad, Noha ^a,c   Robins, Morris J ^a  

^a Brigham Young University   (United States)

^b Moravek Biochemicals Inc   (United States)

^c PFIZER INC   (United States)

Author keywords

5 (Alkyn 1 yl)uracil derivatives; Copper(I) catalyzed cyclizations; Furo 2,3 d pyrimidin 2 ones; Synthesis

Indexed keywords

ANTIVIRUS AGENT; CUPROUS ION; HYDROXYL GROUP; PYRIMIDINONE DERIVATIVE; URACIL DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; SUBSTITUTION REACTION; SYNTHESIS;

CATALYSIS; COPPER; PYRIMIDINONES; URACIL;

EID: 29244460996     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/10810730500265757     Document Type: Article

References (20)

1. Robins, M.J.; Barr, P.J. Nucleic acid related compounds. 31. Smooth and efficient palladium-copper catalyzed coupling of terminal alkynes with 5-iodouracil nucleosides. Tetrahedron Lett. 1981, 22, 421-424.
2. Robins, M.J.; 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. 1983, 48, 1854-1862.
3. De Clercq, E.; Descamps, J.; Balzarini, J.; Giziewicz, J.; Barr, P.J.; Robins, M.J. Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides. J. Med. Chem. 1983, 26, 661-666.
4. McGuigan, C.; Brancale, A.; Barucki, H.; Srinivasan, S.; Jones, G.; Pathirana, R.; Blewett, S.; Alvarez, R.; Yarnold, C.J.; Carangio, A.; Velázquez, S.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Fluorescent bicyclic furo pyrimidine deoxynucleoside analogs as potent and selective inhibitors of VZV and potential future drugs for the treatment of chickenpox and shingles. Drugs of the Fut. 2000, 25, 1151-1161.
5. Balzarini, J.; McGuigan, C. Bicyclic pyrimidine nucleoside analogues (BCNAs) as highly selective and potent inhibitors of varicella-zoster virus replication. J. Antimicrob. Chemother. 2002, 50, 5-9.
6. De Clercq, E. Highly potent and selective inhibition of varicella-zoster virus replication by bicyclic furo[2,3-d]pyrimidine nucleoside analogues. Med. Res. Rev. 2003, 23, 253-274.
7. McGuigan, C.; Barucki, H.; Blewett, S.; Carangio, A.; Erichsen, J.T.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain. J. Med. Chem. 2000, 43, 4993-4997.
8. (a) Miranda, K. Approaches to the synthesis of potential antiviral nucleosides. M.S. Thesis, Brigham Young University, 2001.
9. (b) Robins, M.J.; Miranda, K.; De Clercq, E; Balzarini, J. Unpublished results.
10. McGuigan, C.; Pathirana, R.N.; Snoeck, R.; Andrei, G.; De Clercq, E.; 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. 2004, 47, 1847-1851.
11. Bleackley, R.C.; Jones, A.S.; Walker, R.T. Incorporation of 5-substituted uracil derivatives into nucleic acids-III. Synthesis of 5-substituted uracils derived from 5-acetyluracil. Tetrahedron 1976, 32, 2795-2797.
12. Eger, K.; Jalalian, M.; Schmidt, M. Steric fixation of bromovinyluracil: Synthesis of furo[2,3-d]pyrimidine nucleosides. J. Heterocycl. Chem. 1995, 32, 211-218.
13. Janeba, Z.; Balzarini, J.; Andrei, G.; Snoeck, R.; De Clercq, E.; Robins, M.J. Synthesis and biological evaluation of 5-(alkyn-1-yl)-1-(p- toluenesulfonyl)uracil derivatives. Abstracts of Papers, 229th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 2005; MEDI 435 (manuscript submitted for publication).
14. Balzarini, J.; Sienaert, R.; Liekens, S.; Van Kuilenburg, A.; Carangio, A.; Esnouf, R.; De Clercq, E.; McGuigan, C. Lack of susceptibility of bicyclic nucleoside analogs, highly potent inhibitors of varicella-zoster virus, to the catabolic action of thymidine phosphorylase and dihydropyrimidine dehydrogenase. Mol. Pharmacol. 2002, 61, 1140-1145.
15. Janeba, Z.; Robins, M.J. N-[(2-Hydroxyethoxy)methyl] derivatives of bicyclic furano and pyrrolo pyrimidines and their antiviral evaluation. Antiviral Res. 2004, 62, A64.
16. Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli, F. Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynyipyridines: An easy entry into 2,3-disubstituted furopyridines. Org. Lett. 2002, 4, 2409-2412.
17. Rao, M.S.; Esho, N.; Sergeant C.; Dembinski, R. 5-Endo-dig electrophilic cyclization of α-alkynyl carbonyl compounds: Synthesis of novel bicyclic 5-iodo- and 5-bromofuranopyrimidine nucleosides. J. Org. Chem. 2003, 68, 6788-6790.
18. Petricci, E.; Radi, M.; Corelli, F.; Botta, M. Microwave-enhanced Sonogashira coupling reaction of substituted pyrimidinones and pyrimidine nucleosides. Tetrahedron Lett. 2003, 44, 9181-9184.
19. Robins, M.J.; Vinayak, R.S.; Wood, S.G. Solvent, not palladium oxidation state, is the primary determinant for successful coupling of terminal alkynes with iodo-nucleosides. Tetrahedron Lett. 1990, 31, 3731-3734.
20. Nowak, I.; Robins, M.J. Hydrothermal deamidation of 4-N-acylcytosine nucleoside derivatives: Efficient synthesis of uracil nucleoside esters. Org. Lett. 2005, 7, 4903-4905.