Browse > Article
http://dx.doi.org/10.5012/bkcs.2010.31.9.2473

Synthesis and Antiviral Evaluation of 1'-Branched-5'-Norcarbocyclic Adenosine Phosphonic Acid Analogues  

Oh, Chang-Hyun (Medicinal Chemistry Research Center, Korea Institute of Science and Technology)
Yoo, Kyung-Ho (Medicinal Chemistry Research Center, Korea Institute of Science and Technology)
Hong, Joon-Hee (BK21 Project Team, College of Pharmacy, Chosun University)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.9, 2010 , pp. 2473-2478 More about this Journal
Abstract
Novel 1'-methyl-5'-norcarbocyclic adenosine phosphonic acid analogues were synthesized using an acyclic stereoselective route from commercially available 3,3-diethoxy-propan-1-ol 4. The synthesized nucleoside phosphonate 19 and phosphonic acid 21 were subjected to antiviral screening against various viruses.
Keywords
Antiviral agent; 1'-Branched nucleoside; 5'-Nornucleoside; Phosphonic acid nucleoside;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
1 Boojamra, C. G.; Mackman, R. L.; Markevitch, D. Y.; Prasad, V.; Ray, A. S.; Douglas, J.; Grant, D.; Kim, C. U.; Cihlar, T. Bioorg. Med. Chem. Lett. 2008, 18, 1120.   DOI
2 Mackman, R. L.; Lin, K. Y.; Boojamra, C. G.; Hui, H.; Douglas, J.; Grant, D.; Petrakovsky, O.; Prasad, V.; Ray, A. S.; Cihlar, T. Bioorg. Med. Chem. Lett. 2008, 18, 1116.   DOI
3 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
4 Kadota, I.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6597.   DOI
5 Kim, A.; Hong, J. H. Arch. Pharm. 2005, 338, 522.   DOI
6 Kim, A.; Hong, J. H. Bull. Korean Chem. Soc. 2006, 27, 976.   DOI
7 Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235.
8 Phillion, D. P.; Andrew, S. S. Tetrahedron Lett. 1986, 27, 1477.   DOI   ScienceOn
9 Xu, Y.; Flavin, M. T. Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697.   DOI   ScienceOn
10 Boojamra, C. G.; Parrish, J. P.; Sperandio, D.; Gao, Y.; Petrakovsky, O. V.; Lee, S. K.; Markevitch, D. Y.; Vela, J. E.; Laflamme, G.; Chen, J. M.; Ray, A. S.; Barron, A. C.; Sparacino, M. L.; Desai, M. C. Kim, C. U.; Cihlar, T.; Mackman, R. L. Bioorg. Med. Chem. 2009, 17, 1739.   DOI   ScienceOn
11 Koh, Y. H.; Shim, J. H.; Wu, J. Z.; Zhong, W.; Hong, Z.; Girardet, J. L. J. Med. Chem. 2005, 48, 2867.   DOI
12 Trost, B. M.; Kuo, G. H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621.   DOI
13 Hockova, D.; Holy, A.; Masojídková, M.; Keough, D. T.; de Jersey, J.; Guddat, L. W. Bioorg. Med. Chem. 2009, 17, 6218.   DOI   ScienceOn
14 Lian, L. J.; Yoo, J. C.; Hong, J. H. Nucleosides Nucleotides Nucleic Acids 2009, 28, 150.   DOI   ScienceOn
15 Haraguchi, K.; Kubota, Y.; Tanaka, H. J. Org. Chem. 2004, 69, 1831.   DOI
16 Nakajima, M.; Itoi, K.; Takamatsu, Y. Y.; Kinoshita, T.; Okazaki, T.; Kawakubo, K.; Shindo, M.; Honma, T.; Tohjigamor, M.; Haneishi, T. J. Antibiot. 1991, 44, 293.   DOI
17 Mio, S.; Sano, H.; Shindo, M.; Honma, T.; Sugai, S. Agri. Biol. Chem. 1991, 55, 1105.   DOI
18 Mahmood, K.; Vasella, A.; Bernet, B. Helv. Chem. Acta 1991, 74, 1555.   DOI
19 Elliot, R. D.; Niwas, S.; Riordan, J. M.; Montgomery, J. A.; Secrist, J. A., III. Nucleosides Nucleotides 1992, 11, 97.   DOI
20 Faivre-Buet, V.; Grouiller, A.; Descotes, G. Nucleosides Nucleotides 1992, 11, 1651.   DOI
21 Uteza, V.; Chen, G.-H.; Tuoi, J. L. Q.; Descotes, G.; Fenet, B.; Grouiller, A. Tetrahedron 1993, 49, 8579.   DOI
22 Kodama, T.; Shuto, S.; Nomura, M.; Matsuda, A. Chem. Eur. J. 2001, 7, 2332.   DOI
23 Mackman, R. L.; Boojamra, C. G.; Prasad, V.; Zhang, L.; Lin, K. Y.; Petrakovsky, O.; Babusis, D.; Chen, J.; Douglas, J.; Grant, D.; Hui, H. C.; Kim, C. U.; Markevitch, D. Y.; Vela, J.; Ray, A.; Cihlar, T. Bioorg. Med. Chem. Lett. 2007, 17, 6785.   DOI
24 Ray, A. S.; Vela, J. E.; Boojamra, C. G.; Zhang, L.; Hui, H.; Callebaut, C.; Stray, K.; Lin, K. Y.; Gao, Y.; Mackman, R. L.; Cihlar, T. Antimicrob. Agents Chemother. 2008, 52, 648.   DOI   ScienceOn
25 Mackman, R. L.; Boojamra, C. G.; Prasad, V.; Zhang, L.; Lin, K. Y.; Petrakovsky, O.; Babusis, D.; Chen, J.; Douglas, J.; Grant, D.; Hui, H. C.; Kim, C. U.; Markevitch, D. Y.; Vela, J.; Ray, A.; Cihlar, T. Bioorg. Med. Chem. Lett. 2007, 17, 6785.   DOI
26 Matsuda, A.; Nakajima, Y.; Azuma, A.; Tanaka, M.; Sasaki, T. J. Med. Chem. 1991, 34, 2917.   DOI
27 Ray, A. S.; Vela, J. E.; Boojamra, C. G.; Zhang, L.; Hui, H.; Callebaut, C.; Stray, K.; Lin, K. Y.; Gao, Y.; Mackman, R. L.; Cihlar, T. Antimicrob. Agents Chemother. 2008, 52, 648.   DOI   ScienceOn
28 Takenuki, K.; Matsuda, A.; Ueda, T.; Sasaki, T.; Fujii, A.; Yamagami, K. J. Med. Chem. 1988, 31, 1063.   DOI
29 Yamagami, K.; Fujii, A.; Arita, M.; Okumoto, T.; Sakata, S.; Matsuda, A.; Ueda, T.; Sasaki, T. Cancer Res. 1991, 51, 2319.
30 Azuma, A.; Nakajima, Y.; Nishizono, N.; Minakawa, N.; Suzuki, M.; Hanaoka, K.; Kobayashi, T.; Tanaka, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1993, 36, 4183.   DOI
31 Hattori, H.; Tanaka, M.; Fukushima, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1996, 39, 5005.   DOI
32 Hattori, H.; Nozawa, E.; Iino, T.; Yoshimura, Y.; Shuto, S.; Shimamoto, Y.; Nomura, M.; Fukushima, M.; Tanaka, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1998, 41, 2892.   DOI
33 Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385.   DOI
34 Yuntsen, H.; Ohkuma, K.; Ishii, Y. J. Antibiot. 1956, 9A, 195.
35 Nomura, M.; Shuto, S.; Tanaka, M.; Sasaki, T.; Mori, S.; Shigeta, S.; Matsuda, A. J. Med. Chem. 1999, 42, 2901.   DOI