Browse > Article

Synthesis and Antiviral Activity of Novel C-Methyl Branched Cyclopropyl Nucleosides  

Kwak, Eun-Yee (College of Pharmacy, Chonnam National University)
Hong, Joon-Hee (College of Pharmacy, Chosun University)
Park, Young-Jak (College of Natural Science, Sookmyung Women′s University)
Choi, Bo-Gil (College of Pharmacy, Chonnam National University)
Publication Information
Archives of Pharmacal Research / v.26, no.9, 2003 , pp. 679-685 More about this Journal
Abstract
A series of novel cyclopropyl nucleosides was synthesized using the highly stereoselective Simmons-Smith reaction starting from 1,2:5,6-di-Ο-isopropylidene-D-mannitol. The structural assignments of these nucleosides were determined by NMR studies and X-ray crystallography. All the synthesized nucleosides were assayed against several viruses.
Keywords
Cyclopropyl nucleoside; Antiviral agent; Simmons-Smith cyclopropanation;
Citations & Related Records

Times Cited By Web Of Science : 3  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
  • Reference
1 Iwayama, S., Ono, N., Ohmura, Y., Suzuki, K., Aoki, M., Nakazawa, H., Oikawa, M., Kata, T., Okunishi, M., Nishiyama, Y., and Yamanishi, K., Antiherpesvirus activities of (1'S, 2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'yl]methyl] guanine. Antimicrob. Agents Chemother., 42, 1666-1670 (1998)   PUBMED
2 Jeon, G. S. and Nair, V., New isomeric analogues of anti-HIV active azidonucleosides. Tetrahedron, 52, 12643-12650 (1996)   DOI   ScienceOn
3 Dienstag, J. L., Perrillo, R. P., Schiff, E. R., Bartholomew, M., Vicary, C., and Rubin, M. A., Preliminary trial of lamivudine for chronic hepatitis B infection. New Engl. J. Med., 333, 1657-1661 (1995)   DOI   ScienceOn
4 Furman, P. A., Fyfe, J. A., St. Clair, M. H., Weinhold, K., Rideout, J. L., Freeman, G. A., Lehrman, S. N., Bolognesi, D. P., Broder, S., Mitsuya, H., and Barry, D. W., Phosphorylation of 3'-azido-3'-deoxythymine and selective interaction of the 5'-triphosphate with human immunodeficiency virus reverse transcriptase. Proc. Natl. Acad. Sci. U.S.A., 83, 8333-8337 (1986)   DOI   PUBMED   ScienceOn
5 Sekiyama, T., Hatsuya, S., Tanaka, Y., Uchiyama, M., Ono, N., Iwayama, S., Oikawa, M., Suzuki, K., Okunishi, M., and Tsuji, T., Synthesis and antiviral activity of novel acyclic nucleosides: discovery of cyclopropyl nucleoside with potent inhibitory activity against herpesviruses. J. Med. Chem., 41, 1284-1298 (1998)   DOI   ScienceOn
6 Yarchoan, R., Perno, C. F., Thomas, R. V., Klecker, R. W., Allain, J.-P., Wills, R. J., McAtee, N., Fischl, M. A., Dubinsky, R., McNeely, M. C., Mitsuya, H., Lawley, T. J., Safai, B., Myers, C. E., Pluda, J. M., Leuther, M., Collins, J. M., and Broder, S., Phase 1 studies of 2',3'-dideoxycytidine in severe human immunodeficiency virus infection as a single agent and alternating with zidovudine (AZT). Lancet, 1, 76-81 (1998)
7 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 Krenitsky, T. A., 1592U89, A novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity. Antimicrob. Agents Chemother., 41, 1082-1093 (1997)   PUBMED
8 Lin, T. S., Luo, M. Z., Liu, M. C., Pai, S. B., Dutschman, G. E., and Cheng, Y.-C., Synthesis and biological evaluation of 2',3'-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV). J. Med. Chem., 37, 798-803 (1994)   DOI   ScienceOn
9 Chu, C. K., Ma, T. W., Shanmuganathan, K., Wang, C.-G., Xiang, Y.-J., Pai, S. B., Yao, G.-Q., Sommadossi, J.-P., and Cheng, Y.-C., Use of 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil as a novel antiviral agent for hepatitis B virus and Epstein-Barr virus. Antimicrob. Agents Chemother., 39, 979-981(1995)   DOI   PUBMED   ScienceOn
10 Schinazi, R. F., Chu, C. K., Peck, A., McMillan, A., Mathis, R. Cannon, D., Jeong, L. S., Beach, J. W., Choi, W. B., Yeola, S., and Liotta, D. C., Activities of the four optical isomers of 2',3'-dideoxy-3'-thiacytidine (BCH-189) against human immunodeficiency virus type-1 in human lymphocytes. Antimicrob. Agents Chemother., 36, 672-676 (1992)   DOI   PUBMED   ScienceOn
11 Hukuyama, Y., Hirono, M., and Kodama, M., Total synthesis of (+)-bicyclohumulenone. Chemistry Letter, 167-170 (1992)
12 Hong, J. H., Gao, M. Y., Choi, Y., Cheng, Y. C., Schinazi, R. F., and Chu, C. K., Synthesis of novel 3'-C-methyl-apionucleosides: an asymmetric construction of a quaternary carbon by Claisen rearrangement. Carbohydr. Res., 328, 37-48 (2000)   DOI   ScienceOn
13 Lin, T.-S., Schinazi, R. F., and Prusoff, W. H., Potent and selective in vitro activity of 3'-deoxythymidin-2-ene (3'-deoxy-2',3'-didehydrothymidine) against human immunodeficiency virus. Biochem. Pharmacol., 36, 2713-2718 (1987)   DOI   PUBMED   ScienceOn
14 Qiu, Y. L., Ksebati, M. B., Ptak, R. G., Fan, B. Y., Breitenbach, J. M., Lin, J. S., Cheng, Y. C., Kern, E. R., Drach, J. C., and Zemlicka, J., (Z)- and (E)-2-[(Hydroxymethyl)cyclopropylidene] methyladenine and guanine. New nucleoside analogues with a broad-spectrum antiviral activity. J. Med. Chem., 41, 10-23 (1998)   DOI   ScienceOn
15 Hossain, N., Rozenski, J., De Clercq, E., and Herdewjn, P., Synthesis and antiviral activity of acyclic analogues of 1,5-anhydrohexitol nucleosides using Mitsunobu reaction. Tetrahedron, 52, 13655-13670 (1996)   DOI   ScienceOn
16 Kjellberg, J. and Johansson, N. G., Characterization of $N^7$ and $N^9$ alkylated analogues by $^1H-$ and $^{13}C$-NMR. Tetrahedron, 42, 6541-6544 (1986)   DOI   ScienceOn
17 Arimilli, M. N., Kim, C. U., Dougherty, J., Mulato, A., Oliyai, R., Shaw, J. P., Cundy, K. C., and Bischofberger, N., Synthesis, in vitro biological evaluation and oral bioavailability of 9-[2-[(phosphonomethoxy)propyl]adenine (PMPA) prodrugs. Antivir. Chem. Chemother., 8, 557-564 (1997)   DOI
18 Morikawa, T., Sasaki, H., Mori, K., Shiro, M., and Taguchi, T., Simmons-Smith reaction of fluoroallyl alcohol derivatives. Chem. Pharm. Bull., 40, 3189-3193 (1992)   DOI   ScienceOn
19 Yarchoan, R., Mitsuya, H., Thomas, R. V., Pluda, J. M., Hartman, N. R., Perno, C. F., Marczyk, K. S., Allain, J.-P., Johns, D. G., and Broder, S., In vivo activity against HIV and favorable toxicity profile of 2',3'-dideoxyinosine. Science, 245, 412-415 (1989)   DOI   PUBMED   ScienceOn