Fluorocyclopentenyl-cytosine with broad spectrum and potent antitumor activity

Journal of Medicinal Chemistry

Volumn 55, Issue 9, 2012, Pages 4521-4525

  Choi, Won Jun ^a,b   Chung, Hwa Jin ^c   Chandra, Girish ^a   Alexander, Varughese ^a   Zhao, Long Xuan ^a,d   Lee, Hyuk Woo ^a   Nayak, Akshata ^a   Majik, Mahesh S ^a   Kim, Hea Ok ^a   Kim, Jin Hee ^a   Lee, Young B ^e   Ahn, Chang H ^e   Lee, Sang Kook ^c   Jeong, Lak Shin ^a  

^a Ewha Womans University   (South Korea)

^b Dongguk University   (South Korea)

^c Seoul National University   (South Korea)

^d LIAONING NORMAL UNIVERSITY   (China)

^e Rexan Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXYCYTIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; CYTOSINE DERIVATIVE; FLUOROCYCLOPENTENYL CYTOSINE DERIVATIVE; GEMCITABINE; RIBOSE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BRAIN CANCER; BREAST CANCER; CANCER CELL CULTURE; CANCER INHIBITION; COLON CANCER; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; KIDNEY CANCER; LEUKEMIA; LIVER CANCER; LUNG CANCER; MALE; MELANOMA; MOUSE; NONHUMAN; OVARY CANCER; PANCREAS CANCER; PROSTATE CANCER; STOMACH CANCER; TUMOR XENOGRAFT; UTERINE CERVIX CANCER;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CYCLOPENTANES; CYTOSINE; HUMANS; LUNG NEOPLASMS; MALE; MICE; MICE, NUDE; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84861028393     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3004009     Document Type: Article

References (18)

1. Zhao, L. X.; Yun, M.; Kim, H. O.; Lee, J. A.; Choi, W. J.; Lee, K. M.; Lee, Y. B.; Ahn, C. H.; Jeong, L. S. Design, synthesis, and anticancer activity of fluorocyclopentenyl pyrimidines Nucleic Acids Symp. Ser. 2005, 49, 107-108
2. Yaginuma, S.; Muto, N.; Tsujino, M.; Sudate, Y.; Hayashi, M.; Otani, M. Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation and characterization J. Antibiot. 1981, 34, 359-366 (Pubitemid 11079672)
3. Hayashi, M.; Yaginuma, S.; Yoshioka, H.; Nakatsu, K. Studies on neplanocin A, new antitumor antibiotic. II. Structure determination J. Antibiot. 1981, 34, 675-680 (Pubitemid 11002535)
4. Turner, M. A.; Yang, X.; Yin, D.; Kuczera, K.; Borchardt, R. T.; Howell, P. L. Structure and function of S -adenosylhomocysteine hydrolase Cell Biochem. Biophys. 2000, 33, 101-125
5. Cantoni, G. L. The centrality of S -adenosylhomocysteinase in the regulation of the biological utilization of S -adenosylmethionine. In Biological Methylation and Drug Design; Borchardt, R. T.; Creveling, C. R.; Ueland, P. M., Eds.; Humana Press: Clifton, NJ, 1986; pp 227-238.
6. Keller, B. T.; Borchardt, R. T. Metabolism and mechanism of action of neplanocin A - A potent inhibitor of S -adenosylhomocysteine hydrolase. In Biological Methylation and Drug Design; Borchardt, R. T.; Creveling, C. R.; Ueland, P. M., Eds.; Humana Press: Clifton, NJ, 1986; pp 385-396.
7. Jeong, L. S.; Yoo, S. J.; Lee, K. M.; Koo, M. J.; Choi, W. J.; Kim, H. O.; Moon, H. R.; Lee, M. Y.; Park, J. G.; Lee, S. K.; Chun, M. W. Design, Synthesis and biological evaluation of fluoro-neplanocin A as the novel mechanism-based inhibitor of S -adenosylhomocysteine hydrolase J. Med. Chem. 2003, 46, 201-203 (Pubitemid 36078138)
8. Lee, K. M.; Choi, W. J.; Lee, Y.; Lee, H. J.; Zhao, L. X.; Lee, H. W.; Park, J. G.; Kim, H. O.; Hwang, K. Y.; Heo, Y.-S.; Choi, S.; Jeong, L. S. X-Ray crystal structure and binding mode analysis of human S -adenosylhomocysteine hydrolase complexed with novel mechanism-based inhibitors, halo-neplanocin A analogues J. Med. Chem. 2011, 54, 930-938
9. Marquez, V. E.; Lim, M.-I.; Treanor, S. P.; Plowman, J.; Priest, M. A.; Markovac, A.; Khan, M. S.; Kaskar, B.; Driscol, J. S. Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties J. Med. Chem. 1988, 31, 1687-1694
10. Song, G. Y.; Paul, V.; Choo, H.; Morrey, J.; Sidwell, R. W.; Schinazi, R. F.; Chu, C. K. Enantiomeric synthesis of d-and l -cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus J. Med. Chem. 2001, 44, 3985-3993 (Pubitemid 33051488)
11. Choi, W. J.; Moon, H. R.; Kim, H. O.; Yoo, B. N.; Lee, J. A.; Shin, D. H.; Jeong, L. S. Preparative and stereoselective synthesis of the versatile intermediate for carbocyclic nucleosides: effects of the bulky protecting groups to enforce facial selectivity J. Org. Chem. 2004, 69, 2634-2636 (Pubitemid 38419091)
12. Moon, H. R.; Choi, W. J.; Kim, H. O.; Jeong, L. S. Preparative synthesis of the key intermediate, (4 R,5 R)-3-benzyloxymethyl-4,5- isopropylidenedioxyclopent-2-enone for carbocyclic nucleosides Chem. Lett. 2004, 33, 506-507
13. Jin, Y. H.; Liu, P.; Wang, J.; Baker, R.; Huggins, J.; Chu, C. K. Practical synthesis of d-and l -2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus) J. Org. Chem. 2003, 68, 9012-9018 (Pubitemid 37409551)
14. Parkin, D. M. Global cancer statistics in the year 2000 Lancet Oncol. 2001, 2, 533-543 (Pubitemid 33586866)
15. Dillman, R. O.; Herndon, J.; Seagren, S. L.; Eaton, W. L., Jr.; Green, M. R. Improved survival in stage III non-small cell lung cancer: seven-year follow-up of Cancer and Leukemia Group B (CALGB) 8433 trial J. Natl. Cancer Inst. 1996, 88, 1210-1215 (Pubitemid 26302034)
16. Schiller, J. H.; Harrington, D.; Belani, C. P.; Langer, C.; Sandler, A.; Krook, J.; Zhu, J.; Johnson, D. H. Comparison of four chemotherapy regimens for advanced non-small-cell lung cancer N. Engl. J. Med. 2002, 346, 92-98 (Pubitemid 34438899)
17. Raez, L. E.; Lilenbaum, R. New developments in chemotherapy for advanced non-small cell lung cancer Curr. Opin. Oncol. 2006, 18, 156-161 (Pubitemid 43740436)
18. Cihak, A. Biological effects of 5-azacytidine in eukaryotes Oncology 1974, 30, 405-422