[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2005.26.11.1767

Simple Synthesis of Novel 1',4'-Dimethyl Branched Carbovir Analogues

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

Publication Information

Bulletin of the Korean Chemical Society / v.26, no.11, 2005 , pp. 1767-1770 More about this Journal

Abstract

Novel 1',4'-dimethyl branched carbocyclic nucleosides were synthesized from acetol. The 4'-methyl group was installed via a Claisen rearrangement reaction, and the carbonyl addition of methylmagnesium bromide was used to introduce the 1'-methyl group. The coupling of nucleosidic bases and desilylation was used to produce a series of novel nucleosides.

Keywords

Antiviral agents; Branched nucleoside; Carbocyclic nucleoside;

Citations & Related Records

Times Cited By KSCI : 1 (Citation Analysis)
Times Cited By Web Of Science : 10 (Related Records In Web of Science)
Times Cited By SCOPUS : 10

1	Youssefyeh, R. D.; Verheyden, J. H. P.; Moffatt, J. G. J. Org. Chem. 1979, 44, 1301 DOI
2	Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.; Earl, R. A. Tetrahedron 1994, 50, 10611 DOI ScienceOn
3	Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 5710 DOI ScienceOn
4	Herdewijn, P.; De Clercq, E.; Balzarini, J.; Vanderhaeghe, H. J. Med. Chem. 1985, 28, 550 DOI
5	Vince, R.; Hua, M.; Brownell, J.; Daluge, S.; Lee, F. C.; Shannon, W. M.; Lavelle, G. C.; Qualls, J.; Weisolw, O. S.; Kiser, R. Biochem. Biophys. Res. Commun. 1988, 156, 1046 DOI ScienceOn
6	Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 174 DOI
7	Vince, R. Nucleic Acids Symp. Ser. 1991, 25, 193
8	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.; Krenisky, T. A. Antimicrob. Agents Chemother. 1997, 41, 1082
9	Parker, W. B.; Cheng, Y. C. J. NIH, Res. 1994, 6, 57
10	Chatis, P. A.; Crumpacker, C. S. Antimicrob. Agents Chemother. 1992, 36, 1589 DOI ScienceOn
11	Dias, E. L.; Nguyun, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887 DOI ScienceOn
12	Jenny, T. F.; Horlacher, J.; Previsani, N.; Benner, S. Helv. Chim. Acta 1992, 75, 1944 DOI
13	Wachmeister, J.; Classon, B.; Samuelsson, B. Tetrahedron 1995, 51, 2029 DOI ScienceOn
14	Roy, A.; Schneller, S. W. J. Org. Chem. 2003, 68, 9269 DOI ScienceOn
15	Daiz, Y.; Bravo, F.; Castillon, S. J. Org. Chem. 1999, 64, 6508 DOI ScienceOn
16	Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 1004 DOI ScienceOn
17	Hong, J. H.; Ko, O. H. Bull. Korean Chem. Soc. 2003, 24, 1284 DOI ScienceOn

12	Hua Li. (2008) Nucleosides, Nucleotides and Nucleic Acids Novel Synthesis and Anti-HIV Activity of 4′-Branched Exomethylene Carbocyclic Nucleosides Using a Ring-Closing Metathesis of Triene / 27 (12) , 1238
4	Lian Jin Liu. (2009) Nucleosides, Nucleotides and Nucleic Acids -Nucleosides / 28 (4) , 303
14	Aihong Kim. (2005) Chem Inform Simple Synthesis of Novel 1′,4′-Dimethyl Branched Carbovir Analogues. / 37 (14) , None
10	(2007) Bulletin of the Korean Chemical Society Stereoselective Synthesis of a Novel Cyclohexene Version of Carbovir / 28 (10) , 1645
23	Yoann Aubin. (2007) Tetrahedron Chemoenzymatic synthesis of novel adenosine carbanucleoside analogues containing a locked 3′-methyl-2′,3′-β-oxirane-fused system / 63 (23) , 5050
10	(2008) Bulletin of the Korean Chemical Society Synthesis of Methyl-substituted Bicyclic Carbanucleoside Analogs as Potential Antiherpetic Agents / 29 (10) , 1977
4	(2005) Bulletin of the Korean Chemical Society Synthesis of Novel Mercaptophenyl Carbocyclic C-Nucleoside Analogue Using Sequential [3,3]-Sigmatropic Rearrangement and Ring-closing Metathesis / 29 (4) , 847
12	(2005) Chemical reviews Synthesis of Cyclopentitols by Ring-Closing Approaches / 109 (12) , 6809

1	/ Synlett
2	/ Tetrahedron
3	/ Bulletin of the Korean Chemical Society
4	/ Nucleosides, Nucleotides and Nucleic Acids
5	/ Synlett
6	/ Bulletin of the Korean Chemical Society
7	/ Chemical Reviews
8	/ Bulletin of the Korean Chemical Society
9	/ Nucleosides, Nucleotides and Nucleic Acids
10	/ Chemical Reviews

1	Stereoselective Synthesis of a Novel Cyclohexene Version of Carbovir / [Li, Hua;Hong, Joon-Hee;] / Bulletin of the Korean Chemical Society
2	Synthesis of Methyl-substituted Bicyclic Carbanucleoside Analogs as Potential Antiherpetic Agents / [Kim, Kyung-Ran;Park, Ah-Young;Lee, Hyung-Rock;Kang, Jin-Ah;Kim, Won-Hee;Chun, Pu-Soon;Bae, Jang-Ho;Jeong, Lak-Shin;Moon, Hyung-Ryong;] / Bulletin of the Korean Chemical Society
3	Synthesis of Novel Mercaptophenyl Carbocyclic C-Nucleoside Analogue Using Sequential [3,3]-Sigmatropic Rearrangement and Ring-closing Metathesis / [Li, Hua;Hong, Joon-Hee;] / Bulletin of the Korean Chemical Society