Synthesis and antiviral activities of novel 2′,4′- or 3′,4′-doubly branched carbocyclic nucleosides as potential antiviral agents

Archiv der Pharmazie

Volumn 337, Issue 8, 2004, Pages 457-463

  Oh, Chang Hyun ^a   Hong, Joon Hee ^b  

^a Korea Institute of Science and Technology   (South Korea)

^b Chosun University   (South Korea)

Author keywords

3,3 sigmatropic rearrangement; Carbocyclic nucleosides; Horner Wadsworth Emmons reaction, Antiviral agents

Indexed keywords

1 [4 (HYDROXYMETHYL) 4 PHENYL 3 METHYLCYCLOPENT 2 EN 1 YL]CYTOSINE; 1 [4,4' BIS(HYDROXYMETHYL) 2 METHYLCYCLOPENT 2 EN 1 YL]CYTOSINE; 9 [4 (HYDROXYMETHYL) 4 PHENYL 3 METHYLCYCLOPENT 2 EN 1 YL]ADENINE; 9 [4,4' BIS(HYDROXYMETHYL) 2 METHYLCYCLOPENT 2 EN 1 YL]ADENINE; ADENINE; CARBOCYCLIC NUCLEOSIDE; CARBON; CYTOSINE; GANCICLOVIR; KETONE DERIVATIVE; METHYL GROUP; PALLADIUM; PROPIONIC ACID DERIVATIVE; RIBAVIRIN; TRIETHYL 2 PHOSPHONOPROPIONATE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CATALYST; CONTROLLED STUDY; CYCLIZATION; DRUG SCREENING; DRUG SYNTHESIS; GRIGNARD REACTION; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HORNER WADSWORTH EMMONS REACTION; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; METHODOLOGY; NONHUMAN; PRIORITY JOURNAL;

ANTIVIRAL AGENTS; CELL LINE; CELL SURVIVAL; CYCLIC GMP; HUMANS; INDICATORS AND REAGENTS; NUCLEOSIDES; VIRUSES;

EID: 4544348663     PISSN: 03656233     EISSN: None     Source Type: Journal    
DOI: 10.1002/ardp.200400875     Document Type: Article

References (26)

1. A. D. Borthwick, K. Biggadike, Tetrahedron 1992, 48, 571-623.
2. L. Agrofoglio, E. Suhas, A. Farese, R. Condom, S. Challand, R. A. Earl, R. Guedj, Tetrahedron 1994, 50, 10611-10670.
3. M. T. Crimmins, Tetrahedron 1998, 54, 9229-9272.
4. S. M. Daluge, S. S. Good, M. B. Faletto, W. H. Miller, M. H. StClair, L. R. Boone, M. Tisdale, N. R. Parry, J. E. Reardon, R. E. Dornsife, D. R. Averett, T. A. Krenitsky, Antimicrob. Agents Chemother. 1997, 41, 1082-1093.
5. S. Levine, D. Hernandez, G. Yamanaka, S. Zhang, R. Rose, S. Weinheimer, R. J. Colonno, Antimicrob. Agents Chemother. 2002, 46, 2525-2532.
6. W. A. Slusarchyk, M. G. Young, G. S. Bissacchi, D. R. Hockstein, R. Zahler, Tetrahedron Lett. 1989, 30, 6453-6456.
7. A. D. Borthwick, B. Kirk, K. Biggadike, A. Exall, S. Butt, S. Roberts, D. Knight, J., Ryan, D. Coates, J. Med. Chem. 1991, 34, 907-914.
8. P. M. Price, R. Banerjee, G. Acs, Proc. Natl. Acad. Sci. USA 1989, 86, 8541-8544.
9. S. Hayashi, D. W. Norbeck, W. Rosenbrook, R. L. Fine, M. Matsukura, J. J. Plattner, S. Broder, H. Mitsuya, Antimicrob. Agents Chemother. 1990, 34, 287-294.
10. R. Vince, M. Hua, J. Med. Chem. 1990, 33, 17-21.
11. P. Herdewijn, E. De Clercq, J. Balzarini, H. Vanderhaeghe, J. Med. Chem. 1985, 28, 550-555.
12. J. L. Palmer, R. H. Abeles, J. Biol. Chem. 1979, 254, 1217-1226.
13. P. M. Ueland, Pharmacol. Rev 1982, 34, 223-253.
14. J. L. Hoffman, Arch. Biochem. Biophys. 1980, 205, 132-135.
15. S. Helland, P. M. Ueland, Can. Res. 1982, 42, 1130-1136.
16. J. H. Hong, O. H. Ko, Bull. Kor. Chem. Soc. 2003, 24, 1289-1292.
17. J. H. Hong, Arch. Pharm. Res. 2003, 26, 1109-1116.
18. J. H. Hong, O. H. Ko, Bull. Kor. Chem. Soc. 2003, 24, 1284-1288.
19. O. H. Ko, J. H. Hong, Tetrahedron Lett. 2002, 43, 6399-6402.
20. For a review of RCM, see: R. H. Grubbs, S. Chang, Tetrahedron 1988, 54, 4413-4450.
21. M. E. Maier, Angew. Chem. Int. Ed. 2000, 38, 2073-2077.
22. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29.
23. M. T. Crimmins, B. W. King, W. J. Zuercher, A. L. Choy, J. Org. Chem. 2000, 65, 8499-8500.
24. J. H. Hong, M. J. Shim, B. O. Ro, O. H. Ko, J. Org. Chem. 2002, 67, 6837-6840.
25. R. Snoeck, T. Sakuma, E. De Clercq, I. Rosenberg, A. Holy, Antimicrob. Agents Chemother. 1988, 32, 1839-1844.
26. J. Neyts, R. Snoeck, D. Schols, B. Himpens, E. De Clercq, J. Virol. Methods 1991, 35, 27-38.