Browse > Article
http://dx.doi.org/10.5012/bkcs.2012.33.8.2574

Synthesis and Conformation of Novel 3'-Branched Threosyl-5'-Deoxyphosphonic Acid Nucleoside Analogues  

Shen, Guang Huan (BK-21 Project Team, College of Pharmacy, Chosun University)
Kang, Lien (BK-21 Project Team, College of Pharmacy, Chosun University)
Kim, Eun-Ae (BK-21 Project Team, College of Pharmacy, Chosun University)
Lee, Won-Jae (BK-21 Project Team, College of Pharmacy, Chosun University)
Hong, Joon-Hee (BK-21 Project Team, College of Pharmacy, Chosun University)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.8, 2012 , pp. 2574-2580 More about this Journal
Abstract
The discovery that threosyl phosphonate nucleoside (PMDTA, $EC_{50}=2.53{\mu}M$) is a potent anti-HIV agent has led to the synthesis and biological evaluation of 5'-deoxy versions of threosyl phosphonate nucleosides. In the present study, (E)-3'-phosphonoalkenyl and 3'-phosphonoalkyl nucleoside analogues 13, 16, 20 and 23 were synthesized from acetol and tested for anti-HIV activity and cytotoxicity. The adenine analogue 16 was found to exhibit moderate in vitro anti-HIV-1 activity ($EC_{50}=22.2{\mu}M$).
Keywords
Antiviral agent; Threosyl nucleoside phosphonic acid; Conformation analysis;
Citations & Related Records

Times Cited By Web Of Science : 0  (Related Records In Web of Science)
연도 인용수 순위
  • Reference
1 Vorbruggen, H.; Ruh-Pohlenz, C. New York, Handbook of Nucleoside Synthesis; 2001.
2 Montgomery, J.; Hewson, K. J. Med. Chem. 1969, 12, 498.   DOI
3 Tong, G. L.; Ryan, K. J.; Lee, W. W.; Acton, E. M.; Goodman, L. J. Org. Chem. 1967, 32, 859.   DOI
4 Holy, A.; Votruba, I.; Merta, A.; Cerny, J.; Vesely, J.; Vlach, J.; Sediva, K.; Rosenberg, I.; Otmar, M.; Hrebabecky, H.; Travniekb, M.; Vonkac, V.; Snoeck, R.; De Clercq, E. Antiviral Res. 1990, 13, 295.   DOI   ScienceOn
5 Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E. J. Virol. Methods 1988, 20, 309.   DOI   ScienceOn
6 Kempeneers, V.; Froeyen, M.; Vastmans, K.; Herdewijn, P. Chem. Biodivers 2004, 1, 112.   DOI   ScienceOn
7 Secrist, J. A. 3rd; Riggs, R. M.; Comber, R. N.; Montgomery, J. A. Nucleosides, Nucleotides 1992, 11, 947.   DOI   ScienceOn
8 Montgomery, J. A.; Thomas, H. J.; Kisliuk, R. L.; Gaumont, Y. J. Med. Chem. 1979, 22, 109.   DOI
9 Liu, J. L.; Kim, E. A.; Hong, J. H. Nucleosides, Nucleotides & Nucleic Acids 2012, 31, 411.   DOI
10 Wang, W.; Jin, H.; Fuselli, N.; Mansour, T. S. Bioorg. Med. Chem. Lett. 1997, 7, 2567.   DOI
11 Wu, T.; Froeyen, M.; Kempeneers, V.; Pannecouque, C.; Wang, J.; Busson, R.; De Clercq, E.; Herdewijn, P. J. Am. Chem. Soc. 2005, 127, 5056.   DOI   ScienceOn
12 Koh, Y. H.; Shim, J. H.; Wu, J. Z.; Zhong, W.; Hong, Z.; Girardet, J. L. J. Med. Chem. 2005, 48, 2867.   DOI
13 Kim, C. U.; Luh, B. Y.; Misco, P. F.; Bronson, J. J.; Hitchcock, M. J.; Ghazzouli, I.; Martin, J. C. J. Med. Chem. 1990, 33, 1207.   DOI
14 Hong, J. H. Arch. Pharm. Res. 2007, 30, 131.   DOI
15 Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.   DOI
16 Kumamoto, H.; Topalis, D.; Broggi, J.; Pradere, U.; Roy, V.; Berteina-Raboin, S.; Nolan, S. P.; Deville-Bonne, D.; Andrei, G.; Snoeck, R.; Garin, D.; Crance, J.-M.; Agrofoglio, L. A. Tetrahedron 2008, 64, 3517.   DOI   ScienceOn
17 Montagu, A.; Pradere, U.; Roy, V.; Nolan, S. P.; Agrofoglio, L. A. Tetrahedron 2011, 67, 5317.
18 Huang, Q.; Herdewijn, P. J. Org. Chem. 2011, 76, 3742.   DOI   ScienceOn
19 Hockova, D.; Holy, A.; Masojidkova, M.; Keough, D. T.; De Jersey, J.; Guddat, L. W. Bioorg. Med. Chem. 2009, 17, 6218.   DOI   ScienceOn
20 Robins, M. J.; Uznanski, B. Can. J. Chem. 1981, 59, 2608.   DOI
21 Schoning, K.; Scholz, P.; Guntha, S.; Wu, X.; Krishnamurthy, R.; Eschenmoser, A. Science 2000, 5495, 1347.
22 Holy, A. Curr. Pharm. Des. 2003, 9, 2567.
23 De Clercq, E.; Holy, A. Nat. Rev. Drug Discovery 2005, 4, 928.   DOI
24 Vina, D.; Wu, T.; Renders, M.; Laflamme, G.; Herdewijn, P. Tetrahedron 2007, 63, 2634.   DOI   ScienceOn
25 Kempeneers, V.; Vastmans, K.; Rozenski, J.; Herdewijn, P. Nucleic Acids Res. 2003, 31, 6221.   DOI   ScienceOn
26 Chaput, J. C.; Szostak, J. W. J. Am. Chem. Soc. 2003, 125, 9274.   DOI   ScienceOn