Browse > Article

Synthesis of Novel 1,4-Disubstituted Nucleosides as Potential antitumor Agents  

Kim, Ai-Hong (BK21-Project Team, College of Pharmacy, Chosun University)
Ko, Ok-Hyun (BK21-Project Team, College of Pharmacy, Chosun University)
Hong, Joon-Hee (BK21-Project Team, College of Pharmacy, Chosun University)
Publication Information
YAKHAK HOEJI / v.51, no.2, 2007 , pp. 103-107 More about this Journal
Abstract
In these study novel 1,4-disubstituted carbocyclic nucleoside analogues were synthesized as potential antiviral agents. The coupling reaction of the alcohol 8${\alpha}$ with natural bases using Mitsunobu reaction afforded the target nucleosides 13, 14. The synthesized compounds were evaluated for their antiviral activity against various viruses such as HIV-1, HSV-1, HSV-2 and HCMV. Cytosine derivative 13 exhibited moderate antiviral activity against HIV-1 (EC$_{50}$=16.4 ${\mu}$M).
Keywords
disubstituted carbocyclic nucleoside synthesis; antiviral agents; Mitsunobu reaction;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Herdewijn, P., De Clercq, E., Balzarini, J. and Vanderhaeghe, H. : J. Med. Chem. 28, 550 (1985)
2 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 (1997)
3 Tanaka, M., Norimine, Y., Fujita, T., Suemune, H. and Sakai, K. : Chemoenzymatic synthesis of antiviral carbocyclic nucleosides: Asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl) cyclopentenes using rhizopusdelemar lipase. J. Org. Chem. 61, 6952 (1996)
4 홍준희 : Ring-closing metathesis반응을 이용한 새로운 4-메칠 아데닌 및 유라실 카보사이클릭 뉴크레오사이드의 합성. 약학회지 47, 271 (2003)
5 Kim, A. and Hong, J. H. : Synthesis and anti-HCMV activity of novel 2,3,4-trimethyl branched carbocyclic nucleosides. Nucleosides, Nucleotides & Nucleic Acids 24, 63 (2005)   DOI   ScienceOn
6 Helland, S. and Ueland, P. M. : Inactivation of Sadenosylhomocysteine hydrolase by 9-${\beta}$-D-arabinofuranosyladenine in intact cells. Can Res. 42, 1130 (1982)
7 Agrofoglio, L., Suhas, E., Fares, A., Condom, R., Challand, S. and Earl, R. A. : Synthesis of carbocyclic nucleosides. Tetrahedron 50, 10611 (1994)
8 Roy, A. and Schneller, S. W. : 4'- and 1'-methyl-substituted 5'-norcarbanucleosides. J. Org. Chem. 68, 9269 (2003)   DOI   ScienceOn
9 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 (1999)
10 Borthwick, A. D. and Biggadike, K. : Synthesis of chiral carbocyclic nucleosides. Tetrahedron 48, 571 (1992)
11 Oh, C. H. and Hong, J. H. : Synthesis of novel 4'$\alpha$-phenyl and 5'$\alpha$--methyl branched carbocyclic nucleosides. Bull. Korean Chem. Soc. 26, 1520 (2005)   DOI
12 Wachmeister, J., Classon, B. and Samuelsson, B., Kvarnstrom, I. : Synthesis of 2',3'-dideoxycyclo-2'-pentenyl-3'- C-hydroxymethyl carbocyclic nucleoside analogues as potential anti-viral agents. Tetrahdron 51, 2029 (1995)