Discovery of a new template for anticancer agents: 2′-deoxy-2′- fluoro-4′-selenoarabinofuranosyl-cytosine (2′-F-4′-seleno-ara- C)

Journal of Medicinal Chemistry

Volumn 52, Issue 17, 2009, Pages 5303-5306

  Lak, Shin Jeong ^a   Tosh, Dilip K ^a   Won, Jun Choi ^a   Sang, Kook Lee ^a   Kang, You Jin ^a   Choi, Sun ^a   Jin, Hee Lee ^a   Lee, Hankil ^a   Hyuk, Woo Lee ^a   Hea, Ok Kim ^a  

^a Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXY 2' FLUORO 4' SELENOARABINOFURANOSYLCYTOSINE; 4' SELENONUCLEOSIDE DERIVATIVE; ANTINEOPLASTIC AGENT; CYTARABINE; CYTOSINE DERIVATIVE; DIETHYLAMINOSULFUR TRIFLUORIDE; REAGENT; SELENIUM; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CELL LINE; CONFORMATION; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINATION; HUMAN; HUMAN CELL; NUCLEAR OVERHAUSER EFFECT;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CYTARABINE; CYTOSINE; DRUG DISCOVERY; HALOGENATION; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOSELENIUM COMPOUNDS;

EID: 69949094546     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900852b     Document Type: Article

References (14)

1. Ellison, R. R.; Holland, J. F.; Weil, M.; Jacquillat, C.; Boiron, M.; Bernard, J.; Sawitsky, A.; Rosner, F.; Gussoff, B.; Silver, R. T.; Karanas, A.; Cutter, J.; Spurr, C. L.; Hayes, D. M.; Blom, J.; Leone, L. A.; Haurani, F.; Kyle, R.; Hutchison, J. L.; Forcier, R. J.; Moon, J. H. Arabinosyl cytosine: a useful agent in the treatment of acute leukemia adults. Blood 1968, 32, 507-523.
2. Watanabe, K. A.; Reichman, U.; Hirota, K.; Lopez, C.; Fox, J. J. Nucleosides. 110. Synthesis and antiherpes virus activity of some 2′-fluoro-2′-deoxyarabinofuranosylpyrimidine nucleosides. J. Med. Chem. 1979, 22, 21-24.
3. Miura, S.; Yoshimura, Y.; Endo, M.; Machida, H.; Matsuda, A.; Tanaka, M.; Sasaki, T. Antitumor activity of a novel orally effective nucleoside, 1-(2-deoxy-2-fluoro-4-thio-beta-D-arabinofuranosyl) cytosine. Cancer Lett. 1998, 129, 103-110. (Pubitemid 28375244)
4. Yoshimura, Y.; Kitano, K.; Yamada, K.; Satoh, H.; Watanabe, M.; Miura, S.; Sakata, S.; Sasaki, T.; Maysuda, A. A novel synthesis of 2′-modified 2′-deoxy-4′-thiocytidine from D-glucose. J. Org. Chem. 1997, 62, 3140-3152.
5. Jeong, L. S.; Nicklaus, M. C.; George, C.; Marquez, V. E. Unanticipated retention of configuration in the DAST fluorination of deoxy-4′- thiopyrimidine nucleosides with "UP" hydroxyl groups. Tetrahedron Lett. 1994, 35, 7569-7572.
6. 3-MEM anhydronucleosides. Tetrahedron Lett. 1994, 35, 7573-7576.
7. Jeong, L. S.; Moon, H. R.; Yoo, S. J.; Lee, S. N.; Chun, M. W.; Lim, Y.-H. Ring contraction and rearrangement of 4-thiofuranose derivatives observed during DAST fluorination in the synthesis of L-2′-fluoro-4′- thionucleosides. Tetrahedron Lett. 1998, 39, 5201-5204.
8. Jeong, L. S.; Tosh, D. K.; Kim, H. O.; Wang, T.; Hou, X.; Yun, H. S.; Kwon, Y.; Lee, S. K.; Choi, J.; Zhao, L. X. First synthesis of 4′-selenonucleosides showing unusual southern conformation. Org. Lett. 2008, 10, 209-212.
9. Tosh, D. K.; Choi, W. J.; Kim, H. O.; Lee, Y.; Pal, S.; Hou, X.; Choi, J.; Choi, S.; Jeong, L. S. Stereoselective synthesis and conformational study of novel 2′,3′-didehydro-2′,3′-dideoxy-4′- selenonucleosides. J. Org. Chem. 2008, 73, 4259-4262.
10. Gunaga, P.; Baba, M.; Jeong, L. S. Asymmetric synthesis of novel thioiso dideoxynucleosides with exocyclic methylene as potential antiviral agents. J. Org. Chem. 2004, 69, 3208-3211.
11. Watts, J. K.; Sadalapure, K.; Choubdar, N.; Pinto, B. M.; Damha, M. J. Synthesis and conformational analysis of 2′-fluoro-5-methyl-4′-thio- arabino-uridine (4′S-FMAU). J. Org. Chem. 2006, 71, 921-925. (Pubitemid 43209233)
12. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.; Wallingford CT, 2004.
13. Lee, S. K.; Heo, Y. H.; Steelee, V. E.; Pezzuto, J. M. Induction of apoptosis by 1,4-phenylenebis(methylene)selenocyanate in cultured human colon cancer cells. Anticancer Res. 2002, 22, 97-102. (Pubitemid 34475281)
14. Sivalakshmidevi, A.; Vyas, K.; Om Reddy, G.; Sivaram, S. D. V. N.; Swamy, P. V.; Puranik, R.; Sairam, P. 2′-Deoxy-2′,2′- difluorocytidine monohydrochloride (gemcitabine hydrochloride). Acta Crystallogr., Sect. E: Struct. Rep. Online 2003, 59, o1435-o1437. (Pubitemid 40650723)