Synthesis of nonhydrolyzable analogues of thiazole-4-carboxamide and benzamide adenine dinucleotide containing fluorine atom at the C2' of adenine nucleoside: Induction of K562 differentiation and inosine monophosphate dehydrogenase inhibitory activity

Journal of Medicinal Chemistry

Volumn 40, Issue 16, 1997, Pages 2533-2538

  Lesiak, Krystyna ^a   Watanabe, Kyoichi A ^a   Majumdar, Alokes ^a   Seidman, Michael ^a   Vanderveen, Kristen ^b   Goldstein, Barry M ^b   Pankiewicz, Krzysztof W ^a  

^a Division of Medicinal Chemistry   (United States)

^b UNIVERSITY OF ROCHESTER MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE NUCLEOTIDE; BENZAMIDE; FLUORINE; GUANINE NUCLEOTIDE; INOSINATE DEHYDROGENASE; INOSINE PHOSPHATE; NUCLEOSIDE; TIAZOFURIN;

ARTICLE; CELL DIFFERENTIATION; ENZYME ACTIVITY; ENZYME INHIBITION; GENE REPLICATION; HUMAN; HYDROLYSIS; LEUKEMIA CELL;

ADENINE NUCLEOTIDES; ANIMALS; ANTIMETABOLITES, ANTINEOPLASTIC; BENZAMIDES; CELL DIFFERENTIATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME INHIBITORS; FLUORINE; HUMANS; IMP DEHYDROGENASE; TUMOR CELLS, CULTURED;

EID: 0030848893     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970247f     Document Type: Article

References (15)

1. NAD Analogues. 11. For part 10, see ref 7.
2. Tsutani, H.; Inai, K.; Imamura, S.; Ueda, T.; Nakamura, T. Induction of cell differentiation by IMPDH antisense oligomer in HL-60 and K562 human leukemia cell lines. In Advances in Experimental Medicine and Biology, Vol. 370, Purine and Pyrimidine Metabolism in Man VIII; Sahota, A., Taylor, M., Eds.; Plenum Press: New York, 1995; pp 757-760.
3. Huberman, E.; Glesne, D.; Collart, F. Regulation and role of Inosine-5'-monophosphate dehydrogenase in cell replication, malignant transformation, and differentiation. In Advances in Experimental Medicine and Biology, Vol. 370, Purine and Pyrimidine Metabolism in Man VIII; Sahota, A., Taylor, M., Eds.; Plenum Press: New York, 1995; pp 741-746.
4. Goldstein, B. M.; Leary, J. F.; Farley, B. A.; Marquez, V. E.; Levy, P. C.; Rowley, P. T. Induction of HL60 cell differentiation by tiazofurin and its analogues: Characterization and efficacy. Blood 1991, 78, 593-598.
5. Zatorski, A.; Goldstein, B. M.; Colby, T. D.; Jones, J. P.; Pankiewicz, K. W. Potent inhibitors of human inosine monophosphate dehydrogenase type II. Fluorine-substituted analogues of thiazole-4-carboxamide adenine dinucleotide. J. Med. Chem. 1995, 38, 1098-1105.
6. Marquez, V. E.; Tseng, C. K. H.; Gebeyehu, G.; Cooney, D. A.; Ahluwalia, G. S.; Kelly, J. A.; Dalai, M.; Fuller, R. W.; Wilson, Y. A.; Johns, D. G. Thiazole-4-carboxamide adenine dinucleotide (TAD). Analogues stable to phosphodiesterase hydrolysis. J. Med. Chem. 1986, 29, 1726-1731.
7. Pankiewicz, K. W.; Lesiak, K.; Zatorski, A.; Goldstein, B. M.; Carr, S. F.; Sochacki, M.; Majumdar, A.; Seidman, M.; Watanabe, K. A. The practical synthesis of a methylenebisphosphonate analogue of benzamide adenine dinucleotide: Inhibition of human Inosine monophosphate dehydrogenase (Type I and II) J. Med. Chem. 1997, 40, 1287-1291.
8. Zatorski, A.; Watanabe, K. A.; Carr, S. F.; Goldstein, B. M.; Pankiewicz, K. W. Chemical synthesis of benzamide adenine dinucleotide: Inhibition of Inosine monophosphate dehydrogenase (Types I and II). J. Med. Chem. 1996, 39, 2422-2426.
9. Pankiewicz, K. W.; Krzeminski, L.; Ciszewski, L. A.; Ren, W.-Y.; Watanabe, K. A. A synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine and hypoxanthine. An effect of C3′-endo to C2′-endo conformational shift on the reaction course of 2′-hydroxyl group with DAST. J. Org. Chem. 1992, 57, 553-559.
10. Davisson, V. J.; Davis, D. R.; Dixit, V. M.; Poulter, C. D. Synthesis of Nucleotide 5′-Diphosphates from 5′-O-Tosyl Nucleosides. J. Org. Chem. 1987, 52, 1794-1801.
11. 2-disubstituted pyrophosphates of biological interest. A novel plausible mechanism. J. Am. Chem. Soc. 1997, 119, 3691-3695.
12. Fuertes, M.; Garzia-Lopez, T.; Garzia-Munoz, G.; Stud, M. Synthesis of C-Glycosyl Thiazoles. J. Org. Chem. 1976, 41, 4074-4077.
13. Zatorski, A.; Lipka, P.; Mollova, N.; Schram, K. H.; Goldstein, B. M.; Watanabe, K. A.; Pankiewicz, K. W. Synthesis of thiazole-4-carboxamide adenine difluoromethylene-diphosphonates substituted with fluorine at C-2′ of the adenosine. Carbohydr. Res. 1993, 249, 95-108.
14. Blackburn, G. M.; Eckstein, F.; Kent, D. E.; Perree, T. D. Isopolar vs. Isosteric Phosphonate Analogues of Nucleotides. Nucleosides Nucteotides 1985, 4, 165.
15. Van Aerschot, A.; Balzarini, J.; De Clercq, E.; Herdewijn, P. Synthesis of 3′-fluoro-3′-deoxyribonucleosides: Anti-HIV-1 and cytostatic properties. Nucleosides Nucleotides 1989, 8, 1123-1124.