Synthesis and biological activity of certain 4'-thio-D- arabinofuranosylpurine nucleosides

Journal of Medicinal Chemistry

Volumn 41, Issue 20, 1998, Pages 3865-3871

  Secrist III, John A ^a   Tiwari, Kamal N ^a   Shortnacy Fowler, Anita T ^a   Messini, Lea ^a   Riordan, James M ^a   Montgomery, John A ^a   Meyers, Scott C ^b   Ealick, Steven E ^b  

^a SOUTHERN RESEARCH INSTITUTE   (United States)

^b Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4' THIO DEXTRO ARABINOFURANOSYLPURINE NUCLEOSIDE; GUANINE DERIVATIVE; PURINE NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; NUCLEAR OVERHAUSER EFFECT; PURINE SYNTHESIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

ADENOSINE; ANTINEOPLASTIC AGENTS; CELL DIVISION; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PURINE NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0032563960     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980195+     Document Type: Article

References (36)

1. Montgomery, J. A. Antimetabolites. In Cancer Chemotherapeutic Agents; Foye, W. O., Ed.; American Chemical Society: Washington, DC, 1995; pp 47-109.
2. Mansour, T. S.; Storer, R. Antiviral Nucleosides. Curr. Pharm. Des. 1997, 3, 227-264.
3. Brockman, R. W.; Schabel, F. M., Jr.; Montgomery, J. A. Biologic Activity of 9-β-D-Arabinofuranosyl-2-fluoroadenine, a Metabolically Stable Analogue of 9-β-D-Arabinofuranosyladenine. Biochem. Pharmacol. 1977, 26, 2193-2196.
4. Wright, S. J.; Robertson, L. E.; O'Brien, S.; Plunkett, W.; Keating, M. J. The Role of Fludarabine in Hematological Malignancies. Blood Rev. 1994, 8, 125-134.
5. Montgomery, J. A. Has the Well Gone Dry? The First Cain Memorial Award Lecture. Cancer Res. 1982, 42, 3911-3917.
6. Cheson, B. D. New Antimetabolites in the Treatment of Human Malignancies. Semin. Oncol. 1992, 19, 695-706.
7. Montgomery, J. A.; Shortnacy-Fowler, A. T.; Clayton, S. D.; Riordan, J. M.; Secrist, J. A., III. Synthesis and Biologic Activity of 2′-Fluoro-2-halo Derivatives of 9-β-D-Arabinofuranosyladenine. J. Med. Chem. 1992, 35, 397-401.
8. El Dareer, S. M.; Struck, R. F.; Tillery, K. F.; Rose, L. M.; Brockman, R. W.; Montgomery, J. A.; Hill, D. L. Disposition of 9-β-D-Arabinofuranosyl-2-fluoroadenine in Mice, Dogs, and Monkeys. Drug Metab. Dispos. 1980, 8, 60-63.
9. Hersh, M. R.; Kuhn, J. G.; Phillips, J. L.; Clark, G.; Ludden, T. M.; Von Hoff, D. D. Pharmacokinetic Study of Fludarabine Phosphate (NSC 312887). Cancer Chemother. Pharmacol. 1986, 17, 277-280.
10. Parks, R. E., Jr.; Stoeckler, J. D.; Cambor, C.; Savarese, T. M.; Crabtree, G. W.; Chu, S.-H. Purine Nucleoside Phosphorylase and 5′-Methylthioadenosine Phosphorylase: Targets of Chemotherapy. In Molecular Actions and Targets for Cancer Chemotherapeutic Agents; Sartorelli, A. C., Lazo, J. S., Bertino, J. R., Eds.; Academic Press: New York, 1981; pp 229-252.
11. Secrist, J. A., III; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. Synthesis and Biological Activity of 2′-Deoxy-4′-thio Pyrimidine Nucleosides. J. Med. Chem. 1991, 34, 2361-2366.
12. Secrist, J. A., III; Riggs, R. M.; Tiwari, K. N.; Montgomery, J. A Synthesis and Anti-HIV Activity of 4′-Thio-2′,3′-dideoxynucleosides. J. Med. Chem. 1992, 35, 533-538.
13. Tiwari, K. N.; Montgomery, J. A.; Secrist, J. A., III. The Synthesis and Biological Activity of 1-(2-Deoxy-4-thio-α-L-threopentofuranosyl)thymine. Nucleosides Nucleotides 1993, 12, 841-846.
14. Tiwari, K. N.; Secrist, J. A., III; Montgomery, J. A. Synthesis and Biological Activity of 4′-Thionucleosides of 2-Chloroadenine. Nucleosides Nucleotides 1994, 13, 1819-1828.
15. Secrist, J. A., III; Parker, W. B.; Tiwari, K. N.; Messim, L.; Shaddix, S. C.; Rose, L. M.; Bennett, L. L., Jr.; Montgomery, J. A. The Synthesis and Biological Activity of Certain 4′-Thionucleosides. Nucleosides Nucleotides 1995, 14, 675-686.
16. Parker, W. B.; Shaddix, S. C.; Rose, L. M.; Tiwari, K. N.; Montgomery, J. A.; Secrist, J. A., III; Bennett, L. L., Jr. Metabolism and Metabolic Actions of 4′-Thiothymidme in L1210 Cells. Biochem. Pharmacol. 1995, 50, 687-695.
17. Reist, E. J.; Gueffroy, D. E.; Goodman, L. Synthesis of 4-Thio-D- and -L-ribofuranose and the Corresponding Adenine Nucleosides. J. Am. Chem. Soc. 1964, 86, 5658-5663.
18. Reist, E. J.; Fisher, L. V.; Goodman, L. Thio sugars. Synthesis of the Adenine Nucleosides of 4-Thio-D-xylose and 4-Thio-D-arabinose. J. Org. Chem. 1968, 33, 189-192.
19. Bobek, M.; Whistler, R. L.; Bloch, A. Preparation and Activity of the 4′-Thio Derivatives of Some 6-Substituted Purine Nucleosides. J. Med. Chem. 1970, 13, 411-413.
20. Whistler, R. L.; Doner, L. W.; Nayak, U. G. 4-Thio-D-arabinofuranosylpyrimidine Nucleosides. J. Org. Chem. 1971, 36, 108-110.
21. Bobek, M.; Whistler, R. L.; Bloch, A. Synthesis and Biological Activity of 4′-Thio Analogues of the Antibiotic Toyocamycin. J. Med. Chem. 1972, 15, 168-171.
22. Ototani, N.; Whistler, R. L. Preparation and Antitumor Activity of 4′-Thio Analogues of 2,2′-Anhydro-1-β-D-arabinofuranosylcytosine J. Med. Chem. 1974, 17, 535-537.
23. Bobek, M.; Bloch, A.; Parthasarathy, R.; Whistler, R. L. Synthesis and Biological Activity of 5-Fluoro-4β-thiouridine and Some Related Nucleosides. J. Med. Chem. 1975, 18, 784-787.
24. Miura, G.; Gordon, R.; Montgomery, J. A.; Chiang, P. 4′-Thioadenosine as a Novel Inhibitor of S-adenosylhomocysteine Hydrolase and an Inducer for the Differentiation of HL-60 Human Leukemia Cells. In Purine Pyrimidine Metabolism in Man; Nyhan, E., Thompson, L., Watts, R., Eds.; Plenum Publ. Corp.: New York, 1986; Part B, pp 667-672.
25. Walker, R. T. 4′-Thio-2′-deoxyribonucleosides, Their Chemistry and Biological Properties - a Review. Spec. Publ. - R. Soc. Chem. 1997, 198, 203-237.
26. (a) Whistler, R. L.; Nayak, U. G.; Perkins, A. W., Jr. Anomeric Methyl 4-Thio-D-arabinofuranosides. J. Org. Chem. 1970, 35, 519-521.
27. (b) Fu, Y.-L.; Bobek, M. An Alternative Synthesis of Anomeric Methyl 2-Deoxy-4-thio-D-erythro-pentofuranosides. J. Org. Chem. 1976, 41, 3831-3834.
28. Yoshimura, Y.; Watanabe, M.; Satoh, H.; Ashida, N.; Ijichi, K.; Sakata, S.; Machida, H.; Matsuda, A. A Facile, Alternative Synthesis of 4′-Thioarabinonucleosides and Their Biological Activities. J. Med. Chem. 1997, 40, 2177-2183.
29. Altona, C.; Sundaralingam, M. Conformational Analysis of the Sugar Ring in Nucleosides and Nucleotides. A New Description using the Concept of Pseudorotation. J. Am. Chem. Soc. 1972, 94, 8205-8212.
30. 1H NMR Spectroscopy and X-ray Crystallography. J. Am. Chem. Soc. 1992, 114, 9936-9943.
31. Sheldrick, G. M. Program for the Solution of Crystal Structures; University of Göttingen: Germany, 1986.
32. Sheldrick, G. M. Program for the Refinement of Crystal Structures; University of Göttingen: Germany, 1993.
33. Parker, W. B.; Shaddix, S. C.; Bowdon, B. J.; Rose, L. M.; Vince, R.; Shannon, W. M.; Bennett, L. L., Jr. Metabolism of Carbovir, a Potent Inhibitor of Human Immunodeficiency Virus Type 1, and its Effect on Cellular Metabolism. Antimicrob. Agents Chemother. 1993, 37, 1004-1009.
34. ser-Interferon with γ-Interferon on Human Cell Lines of Various Histogenesis. Cancer Res. 1986, 46, 483-488.
35. Struck, R. F.; Schmid, S. M.; Waud, W. R. Antitumor Activity of Halogen Analogues of Phosphoramide, Isophosphoramide, and Triphosphoramide Mustards, the Cytotoxic Metabolites of Cyclophosphamide, Ifosfamide and Trofosfamide. Cancer Chemother. Pharmacol. 1994, 34, 191-196.
36. Waud, W. R.; Tiwari, A.; Schmid, S. M.; Shih, T.-W.; Strong, J. M.; Hartman, N. R.; O'Reilly, S.; Struck, R. F. 4-Demethylpenclomedine, an Antitumor-active, Potentially nonneurotoxic Metabolite of Penclomedine. Cancer Res. 1997, 57, 815-817.