[KSCI] Korea Science Citation Index Service

Synthesis and Antiviral Activity of Novel Anomeric Branched Carbocyclic Nucleosides

Kim, Ai-Hong (College of Pharmacy, Chosun University)
Hong, Joon-Hee (College of Pharmacy, Chosun University)

Publication Information

Archives of Pharmacal Research / v.28, no.10, 2005 , pp. 1105-1110 More about this Journal

Abstract

Novel anomeric branched carbocyclic nucleosides were synthesized from 1,3-dihydroxy acetone. 4'-Hydroxymethyl was installed by [3,3]-sigmatropic rearrangement reaction and 1'-methyl group was introduced by carbonyl addition of methylmagnesium bromide. The coupling of nucleosidic bases and desilylation afforded a series of novel nucleosides. The synthesized compounds $16{\~}19$ were evaluated for their antiviral activity against HIV-1, HSV-1, HSV-2, and EMCV. Compounds 16 and 19 exhibit toxicity non-related to any anti-HIV-1 activity.

Keywords

Antiviral agents; Anomeric branched carbocyclic nucleoside; [3,3]-Sigmatropic rearrangement;

Citations & Related Records

Times Cited By Web Of Science : 1 (Related Records In Web of Science)
Times Cited By SCOPUS : 1

Reference
Cited By SCOPUS

1	Daluge, S. M., Good, S. S., Faletto, M. B., Miller, W. H., St Clair, M. H., Boone, L. R., Tisdale, M., Parry, N. R., Reardon, J. E., Dornsife, R. E., Averett, D. R., and Krenisky, T. A., 1592U89, A novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity. Antimicrob. Agents Chemother., 41, 1082-1093 (1997)
2	Herdewijn, P., De Clercq, E., Balzarini, J., and Vanderhaeghe, H., Synthesis and antiviral activity of the carbocyclic analogues of (E)-5-(2-halovinyl)-2'-deoxyuridine and (E)-5-(2-halovinyl)-2'-deoxycytidines. J. Med. Chem., 28, 550-555 (1985) DOI PUBMED
3	Jeon, G. S. and Nair, V., New isomeric analogues of anti-HIV active azidonucleosides. Tetrahedron, 52, 12643-12650 (1996) DOI ScienceOn
4	Youssefyeh, R. D., Verheyden, J. H. P., and Moffatt, J. G., 4'-Substituted nucleosides. Hydroxymethylation of nucleoside 5'-aldehyde. J. Org. Chem., 44, 1301-1309 (1979) DOI
5	Daiz, Y., Bravo, F., and Castillon, S., Synthesis of purine and pyrimidine isodideoxynucleosides from (S)-glycydol using iodoetherification as key step. synthesis of (S, S)-iso-ddA. J. Org. Chem., 64, 6508-6511 (1999) DOI ScienceOn
6	Parker, W: B. and Cheng, Y. C., Mitochondrial toxicity of antiviral nucleoside analogues. J. NIH Res., 6, 57-61 (1994)
7	Borthwick, A. D. and Biggadike, K., Synthesis of chiral carbocyclic nucleoside. Tetrahedron, 48, 571-623 (1992) DOI ScienceOn
8	Schwab, P., Grubbs, R. H., and Ziller, J. W., Synthesis and application of $$RuCl_2(=CHR$ : The influence of the alkylidene moiety on metathesis activity. J. Am. Chem. Soc., 118, 100-110 (1996) DOI ScienceOn
9	Agrofoglio, L., Suhas, E., Farese, A., Condom, R., Challand, S., and Earl, R. A., Synthesis of carbocyclic nucleosides. Tetrahedron, 50, 10611-10670 (1994) DOI ScienceOn
10	Chatis, P. A. and Crumpacker, C. S., Resistance of herpesvirus to antiviral drugs. Antimicrob. Agents Chemother., 36, 1589-1595 (1992) DOI ScienceOn
11	Wachmeister, J., Classon, B., and Samuelsson, B., Synthesis of 2' ,3'-dideoxycyclo-2'-pentenyl-3'-C-hydroxymethyl carbo-cyclic nucleoside analogues as potential anti-viral agents. Tetrahedron, 51, 2029-2038 (1995) DOI ScienceOn
12	Dias, E. L., Nguyun, S. T., and Grubbs, R. H., Well-defined Ruthenium olefin metathesis catalysts: Mechanism and activity. J. Am. Chem. Soc., 119, 3887-3897 (1997) DOI ScienceOn
13	Kitano, K., Miura, S., Ohrui, H., and Meguro, H., Synthesis of 4'-C-fluoromethylnucleosides as potential antineoplastic agents. Tetrahedron, 53, 13315-13322 (1997) DOI ScienceOn
14	Ko, O. H. and Hong, J. H., Efficient synthesis of novel carbo-cyclic nucleosides via sequential Claisen rearrangement and ring-closing metathesis. Tetrahedron Lett., 43, 6399-6402 (2002) DOI ScienceOn
15	Jenny, T. F., Horlacher, J., Previsani, N., and Benner, S., Carbocyclic analogs of nucleosides. Part 2. Synthesis of 2',3'-dideoxy-5'-homonucleoside analogs. Helv. Chim. Acta, 75, 1944-1954 (1992) DOI
16	Roy, A. and Schneller, S. W., 4'-, 1'-Methyl SUbstituted 5'-norcarbanucleosides. J. Org. Chem., 68, 9269-9273 (2003) DOI ScienceOn