Synthesis and biological activity of 3- and 5-amino derivatives of pyridine-2-carboxaldehyde thiosemicarbazone

Journal of Medicinal Chemistry

Volumn 39, Issue 13, 1996, Pages 2586-2593

  Liu, Mao Chin ^a   Lin, Tai Shun ^a   Cory, Joseph G ^b   Cory, Ann H ^b   Sartorelli, Alan C ^a  

^a YALE CANCER CENTER   (United States)

^b EAST CAROLINA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (ALLYLAMINO)PYRIDINE 2 CARBOXALDEHYDE THIOSEMICARBAZONE; 5 (ETHYLAMINO)PYRIDINE 2 CARBOXALDEHYDE THIOSEMICARBAZONE; 5 (METHYLAMINO)PYRIDINE 2 CARBOXALDEHYDE THIOSEMICARBAZONE; RIBONUCLEOSIDE DIPHOSPHATE REDUCTASE; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG EFFECT; DRUG OXIDATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; LEUKEMIA CELL LINE; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL DIVISION; CELL SURVIVAL; DNA REPLICATION; ENZYME INHIBITORS; LEUKEMIA L1210; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; PYRIDINES; RIBONUCLEOSIDE DIPHOSPHATE REDUCTASE; THIOSEMICARBAZONES; TUMOR CELLS, CULTURED;

EID: 0029890537     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9600454     Document Type: Article

References (34)

1. Elford, H. L.; Freese, M.; Passamani, E.; Morris, H. P. Ribonucleotide Reductase and Cell Production. J. Biol. Chem. 1970, 245, 5228-5233.
2. Weber, G. Enzymology of Cancer Cells. N. Engl. J. Med. 1977, 296, 486-493.
3. Cory, J. G.; Chiba, P. Combination Chemotherapy Directed at the Components of Nucleoside Diphosphate Reductase. In Inhibitors of Ribonucleoside Diphosphate Reductase Activity; Cory, J. G., Cory, A. M., Eds.; Pergamon Press: New York, 1989; pp 245-264.
4. Sartorelli, A. C.; Agrawal, K. C. Development of α-(N)-Heterocyclic Carboxaldehyde Thiosemicarbazones with Clinical Potential as Antineoplastic Agents. ACS Symp. Ser. 1976, No. 30, Cancer Chemotherapy, 1-14.
5. Krakoff, I. H.; Brown, N. C.; Reichard, P. Inhibition of Ribonucleoside Diphosphate Reductase by Hydroxyurea. Cancer Res. 1968, 28, 1559-1565.
6. Tai, A. W.; Lien, E. J.; Lai, M. M. C.; Khwaja, T. A. Novel N-Hydroxyguanidine Derivatives as Anticancer and Antiviral Agents. J. Med. Chem. 1984, 27, 236-238.
7. Weckbecker, G.; Lien, E. J.; Cory, J. G. Properties of N-Hydroxy-N′-aminoguanidine Derivatives as Inhibitors of Ribonucleotide Reductase. Biochem. Pharmacol. 1988, 37, 529-534.
8. Cory, J. G.; Cory, A. H.; Raber, N. K.; Narayanan, A.; Schneller, S. W. Structural Aspects of N-Hydroxy-N′-aminoguanidine as Inhibitors of L1210 Cell Growth and Ribonucleotide Reductase Activity. Adv. Enzyme Reg. 1993, 33, 129-140.
9. Elford, H. L.; Wampler, G. L.; van't Riet, B. New Ribonucleotide Reductase Inhibitors with Antineoplastic Activity. Cancer Res. 1979, 39, 844-851.
10. van't Riet, B.; Wampler, G. L.; Elford, H. L. Synthesis of Hydroxy- and Amino-Substituted Benzohydroxamic Acids: Inhibition of Ribonucleotide Reductase and Antitumor Activity. J. Med. Chem. 1979, 22, 589-593.
11. Liu, M. C.; Lin, T. S.; Sartorelli, A. C. Chemical and Biological Activity of α-(N)-Heterocyclic Carboxaldehyde Thiosemicarbazones. In Progress in Medicinal Chemistry, Vol. 32; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier: Amsterdam, 1995; pp 1-35.
12. Sartorelli, A. C.; Agrawal, K. C.; Tsiftsoglou, A. S.; Moore, E. C. Characterization of the Biochemical Mechanism of Action of α-(N)-Heterocyclic Carboxaldehyde Thiosemicarbazones. Adv. Enzyme Reg. 1977, 15, 117-139.
13. Creasey, W. A.; Agrawal, K. C.; Capizzi, R. L.; Stinson, K. K.; Sartorelli, A. C. Studies on the Antineoplastic Activity and Metabolism of α-(N)-Hetrocyclic Carboxaldehyde Thiosemicarbazones in Dogs and Mice. Cancer Res. 1972, 32, 565-572.
14. French, F. A.; Blanz, E. J., Jr. α-(N)-Formylheteroaromatic Thiosemicarbazones. Inhibition of Tumor-Derived Ribonucleoside Diphosphate Reductase and Correlation with In Vivo Antitumor Activity. J. Med. Chem. 1974, 17, 172-181.
15. Sunkara, P. S.; Lippert, B. J.; Snyder, R. D.; Jarvi, E. T.; Farr, R. A. Antitumor Activity of 2′-Deoxy-2′,2′-difluorocytidine, a Novel Inhibitor of Ribonucleotide Reductase. Proc. Am. Assoc. Cancer Res. 1988, 29, 324.
16. Heinemann, V.; Xu, Y. Z.; Chubb, S.; Sen, A.; Hertel, L. W.; Grindey, G. B.; Plunkett, W. Inhibition of Ribonucleotide Reduction in CCRF-CEM Cells by 2′,2′-Difluorodeoxycytidine. Mol. Pharmacol. 1990, 38, 567-572.
17. Baker, C. H.; Banzon, J.; Bollinger, J. M.; Stubbe, J.; Samano, V.; Robins, M. J.; Lippert, B.; Jarvi, E.; Resvick, R. 2′-Deoxy-2′-methylenecytidine and 2′-Deoxy-2′,2′-difluorocytidine 5′-Diphosphates: Potent Mechanism-Based Inhibitors of Ribonucleotide Reductase. J. Med. Chem. 1991, 34, 1879-1884.
18. Tseng, W. C.; Derse, D.; Cheng, Y. C.; Brockman, R. W.; Bennett, L. L., Jr. In Vitro Biological Activity of 9-β-D-Arabinofuranosyl-2-fluoroadenine and the Biochemical Actions of its Triphosphate on DNA Polymerases and Ribonucleotide Reductase from HeLa Cells. Mol. Pharmacol. 1982, 21, 474-477.
19. Huang, M. C.; Ashmun, R. A.; Avery, T. L.; Kuehl, M.; Blakley, R. L. Effects of Cytotoxicity of 2-Chloro-2′-deoxyadenosine on Cell Growth, Clonogenicity, DNA Synthesis, and Cell Cycle Kinetics. Cancer Res. 1986, 46, 2362-2368.
20. Huang, P.; Chubb, S.; Hertel, L. W.; Grindey, G. B.; Plunkett, W. Action of 2′,2′-Difluorodeoxycytidine on DNA Synthesis. Cancer Res. 1991, 57, 6110-6117.
21. DeConti, R. C.; Toftness, B. R.; Agrawal, K. C.; Tomchick, R.; Mead, J. A. R.; Bertino, J. R.; Sartorelli, A. C.; Creasey, W. A. Clinical and Pharmacological Studies with 5-Hydroxy-2-formylpyridine Thiosemicarbazone. Cancer Res. 1972, 32, 1455-1462.
22. Krakoff, I. H.; Etcubanas, E.; Tan, C.; Mayer, K.; Bethune, V.; Burchenal, J. H. Clinical Trial of 5-Hydroxypicolinaldehyde Thiosemicarbazone (5-HP; NSC-107392), With Special Reference to Its Iron-Chelating Properties. Cancer Chemother. Rep. 1974, 58, 207-212.
23. Wang, Y.; Liu, M. C.; Lin, T. S.; Sartorelli, A. C. Synthesis and Antitumor Activity of 3- and 5-Hydroxy-4-methylpyridine-2-carboxaldehyde Thiosemicarbazones. J. Med. Chem. 1992, 35, 3667-3671.
24. Liu, M. C.; Lin, T. S.; Sartorelli, A. C. Synthesis and Antitumor Activity of Amino Derivatives of Pyridine-2-carboxaldehyde Thiosemicarbazone. J. Med. Chem. 1992, 35, 3672-3677.
25. Liu, M. C.; Lin, T. S.; Penketh, P.; Sartorelli, A. C. Synthesis and Antitumor Activity of 4- and 5-Substituted Derivatives of Isoquinoline-1-carboxaldehyde Thiosemicarbazone. J. Med. Chem. 1995, 38, 4234-4243.
26. Cory, J. G.; Cory, A. H.; Rappa, G.; Lorico, A.; Liu, M. C.; Lin, T. S.; Sartorelli, A. C. Inhibitors of Ribonucleotide Reductase: Comparative Effects of Amino- and Hydroxy-Substituted Pyridine-2-carboxaldehyde Thiosemicarbazones. Biochem. Pharmacol. 1994, 48, 335-344.
27. Cory, J. G.; Cory, A. H.; Rappa, G.; Lorico, A.; Liu, M. C.; Lin, T. S.; Sartorelli, A. C. Structure-Function Relationships for a New Series of Pyridine-2-carboxaldehyde Thiosemicarbazones on Ribonucleotide Reductase Activity and Tumor Cell Growth in Culture and in Vivo. Adv. Enzyme Reg. 1995, 35, 55-68.
28. Barluenga, J.; Bayon, A. M.; Asensio, G. A New and Specific Method for the Monomethylation of Primary Amines. J. Chem. Soc., Chem. Commun. 1984, 1334-1335.
29. Liu, M. C.; Lin, T. S.; Sartorelli, A. C. A One-Pot Synthesis of 3-Nitro- and 3,5-Dinitro-2-picolines. Synth. Commun. 1990, 20, 2965-2970.
30. Achremowicz, L. Synthesis of 3,5-Dinitropyridine Aldehydes. Il Farmaco Ed. Sci. 1978, 35, 161-166.
31. Kingsbury, W. D.; Boehm, J. C.; Jakas, D. R.; Holden, K. G.; Heicht, S. M.; Gallagher, G.; Caranfa, M. J.; McCabe, F. L.; Faucette, L. F.; Johnson, R. K.; Hertzberg, R. P. Synthesis of Water-Soluble (Aminoalkyl)camptothecin Analogues: Inhibition of Topoisomerase I and Antitumor Activity. J. Med. Chem. 1991, 34, 98-107.
32. Lin, T. S.; Xu, S. P.; Zhu, L. Y.; Cosby, L. A.; Sartorelli, A. C. Synthesis of 2,3-Diaziridinyl-1,4-naphthoquinone Sulfonate Derivatives as Potential Antineoplastic Agents. J. Med. Chem. 1989, 32, 1467-1471.
33. Steeper, J. R.; Steuart, C. E. A Rapid Assay for CDP Reductase Activity in Mammalian Cell Extracts. Anal. Biochem. 1970, 34, 123-130.
34. Cory, A. H.; Owen, T. C.; Barltrop, J. A.; Cory, J. G. Use of an Aqueous Soluble Tetrazolium/Formazan Assay for Cell Growth Assays in Culture. Cancer Commun. 1991, 3, 207-212.