Browse > Article
http://dx.doi.org/10.5012/bkcs.2014.35.12.3502

Synthesis and Potent Anti-leukemic Activity of Novel 5'-Norcarbocyclic C-nucleoside Phosphonic Acids  

Kim, Seyeon (BK21-Project Team, College of Pharmacy, Chosun University)
Kim, Eunae (BK21-Project Team, College of Pharmacy, Chosun University)
Oh, Chang-Hyun (Center for Biomaterials, Korea Institute of Science and Technology)
Yoo, Kyung Ho (Chemical Kinomics 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.35, no.12, 2014 , pp. 3502-3508 More about this Journal
Abstract
The first synthetic route to 5'-norcarbocyclic C-nucleoside [7-oxa-7,9-dideazadenosine (furo[3,2-d]pyrimidine) and 9-deazaadenosine (pyrrolo[3,2-d]pyrimidine)] phosphonic acids from commercially available 1,3-dihydroxy cyclopentane was described. The key C-C bond formation from sugar to base precursor was performed using Knoevenagel-type condensation from a ketone derivative. Synthesized C-nucleoside phosphonic acids were tested for anti-HIV activity as well as anti-leukemic activity. Compound 26 showed significant anti-leukemic activity.
Keywords
Antiviral agent; Anti-leukemic agent; C-nucleoside; Knoevenagel reaction;
Citations & Related Records
연도 인용수 순위
  • Reference
1 (b) Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697-7701.   DOI   ScienceOn
2 Hockova, D.; Holy, A.; Masojidkova, M.; Keough, D. T.; De Jersey, J.; Guddat, L. W. Bioorg. Med. Chem. 2009, 17, 6218-6232.   DOI   ScienceOn
3 Lim, M. I.; Klein, R. S. Tetrahedron Lett. 1981, 22, 25-28.   DOI   ScienceOn
4 Kamath, V. P.; Ananth, S.; Bantia, S.; Morris, P. E. J. Med. Chem. 2004, 47, 1322-1324.   DOI
5 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, 295-311.   DOI   ScienceOn
6 Fischer, G. A. Ann. N.Y. Acad. Sci. 1958, 76, 673-680.   DOI
7 Burchenal, J. H.; Chou, T.-C.; Lokye, L.; Smith, R. S.; Watanabe, K. A.; Su, T.-L.; Fox, J. J. Cancer Res. 1982, 42, 2598-2600.
8 (f) Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235-250.   DOI
9 (e) Ariona, O.; Gomez, A. M.; Lopez, J. C.; Plumet, J. Chem. Rev. 2007, 107, 1919-2036.   DOI   ScienceOn
10 (g) Boutureira, O.; Matheu, M. I.; Diazm, Y.; Castillon, S. Chem. Soc. Rev. 2013, 42, 5056-5072.   DOI
11 Stoeckler, J. D.; Cambor, C.; Parks, R. E., Jr. Biochemistry 1980, 19, 102-107.   DOI   ScienceOn
12 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
13 Kim, C. U.; Luh, B. Y.; Martin, J. C. J. Org. Chem. 1991, 56, 2642-2647.   DOI
14 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
15 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
16 (a) De Clercq, E. Biochem. Pharmacol. 2011, 82, 99-109.   DOI
17 Bhattacharya, B. K.; Otter, B. A.; Berens, R. L.; Klein, R. S. Nucleosides Nucleotides 1990, 9, 1021-1043.   DOI
18 (b) Balzarini, J.; Hao, Z.; Herdewijn, P.; Johns, D. G.; De Clercq, E. Proc. Natl. Acad. Sci. USA 1991, 88, 1499-1503.   DOI   ScienceOn
19 Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.   DOI
20 Chun, B. K.; Song, G. Y.; Chu, C. K. J. Org. Chem. 2001, 66, 4852-4858.   DOI   ScienceOn
21 Rao, K. V. B.; Ren, W.-Y.; Burchenal, J. H.; Klein, R. S. Nucleosides Nucleotides 1986, 5, 539-569.   DOI
22 (a) Phillion, D. P.; Andrew, S. S. Tetrahedron Lett. 1986, 27, 1477-1480.   DOI   ScienceOn
23 (b) Zimmerman, T. P.; Deeprose, R. D.; Wolberg, G.; Stopford, C. R.; Duncan, G. S.; Miller, W. H.; Miller, R. L.; Lim, M. I.; Ren, W. Y.; Klein, R. S. Biochem. Pharmacol. 1983, 32, 1211-1217.   DOI   ScienceOn
24 (a) Tam, S. Y.-K.; Klein, R. S.; Wempen, I.; Fox, J. J. J. Org. Chem. 1979, 44, 4547-4553.   DOI
25 (b) Tam, S. Y.-K.; Hwang, J. S.; De Las Heras, F. G.; Klein, R. S.; Fox, J. J. J. Heterocycl. Chem. 1976, 13, 1305-1308.   DOI
26 (a) Fissekis, J. D.; Creegan, B. M. J. Org. Chem. 1967, 32, 3595-3603.   DOI
27 (b) Katagiri, N.; Haneda, T.; Kaneko, C. Chem. Pharm. Bull. 1986, 34, 4875-4878.   DOI
28 (c) Katagiri, N.; Haneda, T.; Hayasaka, E.; Watanabe, N.; Kaneko, C. J. Org. Chem. 1988, 53, 226-227.   DOI
29 (d) Lee, C. H.; Kim, J. Y.; Kim, W. J.; Kim, Y. H. Heterocycles 1990, 31, 211-214.   DOI
30 (f) Coockson, R. C.; Dufield, P. J.; Scopes, D. I. C. J. Chem. Soc., Perkin Trans. 1 1986, 393-398.
31 (g) Takahashi, T.; Kotsubo, H.; Koizumi, T. Tetrahedron: Asymmetry 1991, 2, 1035-1040.   DOI   ScienceOn
32 (h) Zhou, J.; Yang, M.; Schnell, S. W. Tetrahedron Lett. 2004, 45, 8233-8234.   DOI   ScienceOn
33 Zhou, J.; Yang, M.; Akdag, A.; Wang, H.; Schneller, S. W. Tetrahedron 2008, 64, 433-438.   DOI
34 (a) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571-623.   DOI   ScienceOn
35 (b) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768.   DOI
36 (c) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670.   DOI   ScienceOn
37 (d) Crimmins, M. T. Tetrahedron 1998, 54, 9229-9272.   DOI   ScienceOn
38 (c) Liang, C.; Ma, T.; Cooperwood, J. S.; Du, J.; Chu, C. K. Carbohydr. Res. 1997, 303, 33-38.   DOI   ScienceOn
39 (a) Shaban, M. A. E.; Nasr, A. Z. Adv. Heterocycl. Chem. 1997, 68, 223-432.   DOI
40 (b) Shaban, M. A. E. Adv. Heterocycl. Chem. 1997, 70, 163-337.   DOI
41 (d) Zhou, J.; Yang, M.; Akdag, A.; Wang, H.; Schneller, S. W. Tetrahedron 2008, 64, 433-438.   DOI
42 Buchenal, J. H.; Ciovacco, K.; Kalaher, K.; O'Toole, T.; Kiefner, R.; Dowing, M. D.; Chu, C. K.; Watanabe, K. A.; Wempen, I.; Fox, J. J. Cancer Res. 1976, 36, 1520-1523.
43 (b) Srivastava, P. C.; Pickering, M. V.; Allen, L. B.; Streeter, D. C.; Campbell, M. T.; Witkowski, J. T.; Sidwell, R. W.; Robins, R. K. J. Med. Chem. 1977, 20, 256-262.   DOI
44 Srivastava, P. C.; Robins, R. K. J. Med. Chem. 1983, 26, 445-448.   DOI
45 (a) Fuertes, M.; Garcia-Lopez, M. T.; Garcia-Munoz, G.; Stud, M. J. Org. Chem. 1976, 41, 4074-4077.   DOI
46 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
47 Koh, Y. H.; Shim, J. H.; Wu, J. Z.; Zhong, W.; Hong, Z.; Girardet, J. L. J. Med. Chem. 2005, 48, 2867-2875.   DOI   ScienceOn
48 (e) Katagiri, N.; Tomura, M.; Haneda, T.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1987, 19, 1422-1423.
49 (a) Chu, C. Y.; Zuckerman, L. B.; Sato, S.; Crabtree, G. W.; Bogden, A. E.; Lim, M. I.; Klein, R. S. Biochem. Pharmacol. 1984, 33, 1229-1234.   DOI   ScienceOn