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http://dx.doi.org/10.5012/bkcs.2014.35.9.2743

Efficient Synthesis of Novel 4'-Trifluoromethyl-5'-norcarbocyclic Purine Phosphonic Acid Analogs by Using the Ruppert-Prakash Reaction  

Kim, Seyeon (BK-21 Project Team, College of Pharmacy, Chosun University)
Kim, Eunae (BK-21 Project Team, College of Pharmacy, Chosun University)
Yoo, Jin Cheol (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.35, no.9, 2014 , pp. 2743-2748 More about this Journal
Abstract
Novel 4'-trifluoromethyl-5'-norcarbocyclic purine phosphonic acid analogs were efficiently synthesized from commercially available 1,3-dihydroxy cyclopentane (5). Trifluoromethylation was successfully performed by using the Ruppert-Prakash reaction. The purine nucleosidic bases were efficiently coupled by using the Mitsunobu reaction. The synthesized adenosine phosphonic acids analogs 13 and 16 were screened for antiviral activity against human immunodeficiency virus-1 (HIV-1). Adenine derivative 13 exhibited significant anti-HIV-1 activity.
Keywords
Anti-HIV agents; 4'-Branched carbocyclic nucleoside; Phosphonic acid nucleosides;
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1 (b) Fleet, G. W. J.; Son, J. C.; Derome, A. E. Tetrahedron 1988, 44, 625-636.   DOI   ScienceOn
2 (c) Patrick, T.; Ye, W. J. Fluorine Chem. 1998, 90, 53-55.   DOI   ScienceOn
3 (e) McAtee, J. J.; Schinazi, R. F.; Liotta, D. C. J. Org. Chem. 1998, 63, 2161-2167.   DOI   ScienceOn
4 (f) Lee, K.; Choi, Y.; Gullen, E.; Schlueter-Wirtz, S.; Schinazi, R. F.; Cheng, Y. C.; Chu, C. K. J. Med. Chem. 1999, 42, 1320-1328.   DOI   ScienceOn
5 (a) Hertel, L. W.; Kroin, J. S.; Misner, J. W.; Tustin, J. M. J. Org. Chem. 1988, 53, 2406-2409.   DOI
6 (b) Xiang, Y.; Kotra, L. P.; Chu, C. K.; Schinazi, R. F. Bioorg. Med. Chem. Lett. 1995, 5, 743-748.   DOI   ScienceOn
7 (c) Fernandez, R.; Matheu, M. I.; Echarri, R.; Castillon, S. Tetrahedron 1998, 54, 3523-3532.   DOI   ScienceOn
8 (a) Roy, A.; Schneller, S. W. Tetrahedron Lett. 2005, 46, 8913-8915   DOI   ScienceOn
9 (b) Zhang, X.; Qing, F.-L. J. Org. Chem. 2002, 67, 1016-1019   DOI   ScienceOn
10 Boojamra, C. G.; Parrish, J. P.; Sperandio, D.; Gao, Y.; Petrakovsky, O. V.; Lee, S. K.; Markevich, 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, 1739-1746.   DOI   ScienceOn
11 Lian, L. J.; Yoo, J. C.; Hong, J. H. Nucleosides Nucleotides Nucleic Acids 2009, 28, 150-164.   DOI   ScienceOn
12 Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E. J. Virol. Methods 1988, 20, 309-321.   DOI   ScienceOn
13 Kim, C. U.; Luh, B. Y.; Martin, J. C. J. Org. Chem. 1991, 56, 2642-2647.   DOI
14 Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.   DOI
15 Lavaire, S.; Plantier-Royon, R.; Portella, C. J. Carbohydr. Chem. 1996, 15, 361-370.   DOI
16 (a) Singh, R. P.; Shreeve, J. M. Tetrahedron 2000, 56, 7613-7632.   DOI   ScienceOn
17 (b) Stahly, G. P.; Bell, D. R. J. Org. Chem. 1989, 54, 2873-2877.   DOI
18 (c) Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393-395.   DOI
19 (d) Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757-786.   DOI   ScienceOn
20 (b) Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701.   DOI   ScienceOn
21 (a) Tanaka, M.; Norimine, Y.; Fujita, T.; Suemune, H.; Sakai, K. J. Org. Chem. 1996, 61, 6952-6957.   DOI   ScienceOn
22 (b) Liu, L. J.; Kim, S. W.; Lee, W.; Hong, J. H. Bull. Korean Chem. Soc. 2009, 30, 2989-2992.   DOI   ScienceOn
23 Chong, Y. H.; Gumina, G.; Chu, C. K. Tetrahedron: Asymmetry 2000, 11, 4853-4875.   DOI   ScienceOn
24 Hockova, D.; Holy, A.; Masojidkova, M.; Keough, D. T.; De Jersey, J.; Guddat, L. W. Bioorg. Med. Chem. 2009, 17, 6218-6232.   DOI   ScienceOn
25 (c) Jeannot, F.; Mathe, C.; Gosselin, G. Nucleosides Nucleotides Nucleic Acids 2001, 20, 755-758.   DOI   ScienceOn
26 Robins, M. J.; Uznanski, B. Can. J. Chem. 1981, 59, 2608-2611.   DOI
27 Montgomery, J.; Hewson, K. J. Med. Chem. 1969, 12, 498-504.   DOI
28 Tong, G. L.; Ryan, K. J.; Lee, W. W.; Acton, E. M. Goodman, L. J. Org. Chem. 1967, 32, 859-862.   DOI
29 (d) Jeannot, F.; Gosselin, G.; Standring, D.; Bryant, M.; Sommadossi, J.-P.; Loi, A. G.; Colla, P. L.; Mathe, C. Bioorg. Med. Chem. 2002, 10, 3153-3161.   DOI   ScienceOn
30 (e) Serafinowski, P. J.; Brown, C. A. Tetrahedron 2000, 56, 333-339.   DOI   ScienceOn
31 Miethchen, R. J. Fluorine Chem. 2004, 125, 895-901.   DOI   ScienceOn
32 Coderre, J. A.; Santi, D. V.; Matsuda, A.; Watanabe, K. A.; Fox, J. J. J. Med. Chem. 1983, 26, 1149-1152.   DOI
33 Hudlicky, M.; Pavlath, A. E., Eds.; Chemistry of Organic Fluorine Compounds II; American Chemical Society: Washington, DC, 1995.
34 Kozak, J.; Johnson, C. R. Nucleosides Nucleotides 1998, 17, 2221-2239.   DOI   ScienceOn
35 Wu, T.; Froeyen, M.; Kempeneers, V.; Pannecouque, C.; Wang, J.; Busson, R.; De Clercq, E.; Herdewijn, P. J. Am. Chem. Soc. 2005, 127, 5056-5065.   DOI   ScienceOn
36 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, 1207-1213.   DOI
37 (g) Lee, K. C.; Choi, Y.; Hong, J. H.; Schinazi, R. F.; Chu, C. K. Nucleosides Nucleotides 1999, 18, 537-540.   DOI
38 (b) 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, 1120-1123.   DOI   ScienceOn
39 (c) Cihlar, T.; Ray, A. S.; Boojamra, C. G.; Zhang, L.; Hui, H.; Laflamme, G.; Vela, J. E.; Grant, D.; Chen, J.; Myrick, F.; White, K. L.; Gao, Y.; Lin, K. Y.; Douglas, J. L.; Parkin, N. T.; Carey, A.; Pakdaman, R.; Mackman, R. L. Antimicrob. Agents Chemother. 2008, 52, 655-665.   DOI   ScienceOn
40 (a) Okabe, M.; Sun, R.; Zenchoff, G. B. J. Org. Chem. 1991, 56, 4392-4397.   DOI
41 (a) 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, 648-654.   DOI   ScienceOn
42 (a) Phillion, D. P.; Andrew, S. S. Tetrahedron Lett. 1986, 27, 1477-1480.   DOI   ScienceOn
43 Li, N.-S.; Tang, X.-Q.; Piccirilli, J. A. Org. Lett. 2001, 3, 1025-1028.   DOI   ScienceOn