Synthesis, conformational analysis, and biological activity of C- thioribonucleosides related to tiazofurin

Journal of Medicinal Chemistry

Volumn 43, Issue 7, 2000, Pages 1264-1270

  Franchetti, Palmarisa ^a   Marchetti, Stefano ^a   Cappellacci, Loredana ^a   Jayaram, Hiremagalur N ^b   Yalowitz, Joel Aaron ^b   Goldstein, Barry M ^c   Barascut, Jean Louis ^d   Dukhan, David ^d   Imbach, Jean Louis ^d   Grifantini, Mario ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF ROCHESTER MEDICAL CENTER   (United States)

^d CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN THIOFURIN; FURANFURIN; GUANOSINE TRIPHOSPHATE; INOSINATE DEHYDROGENASE; INOSINE PHOSPHATE; OXAZOFURIN; RIBONUCLEOSIDE DERIVATIVE; THIOPHENFURIN; THIOPHENTHIOFURIN; TIAZOFURIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CONTROLLED STUDY; CYTOTOXICITY; DEACETYLATION; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; GLYCOSYLATION; HUMAN; HUMAN CELL; LEUKEMIA CELL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; FURANS; GLYCOSYLATION; HUMANS; IMP DEHYDROGENASE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; RIBAVIRIN; RIBONUCLEOSIDES; RIBOSE; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS; THIOPHENES; TUMOR CELLS, CULTURED;

EID: 0034611616     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990257b     Document Type: Article

References (17)

1. Franchetti, P.; Cappellacci, L.; Grifantini, M. IMP Dehydrogenase as a Target of Antitumor and Antiviral Chemotherapy. Farmaco 1996, 51, 457-469 and references therein.
2. Franchetti, P.; Cappellacci, L.; Grifantini, M.; Barzi, A.; Nocentini, G.; Yang, H.; O'Connor, A.; Jayaram, H. N.; Carrell, C.; Goldstein, B. M. Furanfurin and Thiophenfurin: Two Novel Tiazofurin Analogues. Synthesis, Structure, Antitumor Activity and Interactions with IMP Dehydrogenase. J. Med. Chem. 1995, 38, 3829-3837.
3. Franchetti, P.; Cappellacci, L.; Perlini, P.; Jayaram, H. N.; Butler, A.; Schneider, B. P.; Collart, F. R.; Huberman, E.; Grifantini M. Isosteric Analogues of Nicotinamide Adenine Dinucleotide Derived from Furanfurin, Thiophenfurin, and Selenophenfurin as Mammalian Inosine Monophosphate Dehydrogenase (Type I and II) Inhibitors. J. Med. Chem. 1998, 41, 1702-1707.
4. Leydier, C.; Bellon, L.; Barascut J.-L.; Deydier, J.; Maury, G.; Pelicano, H.; El Alaoui, M. A.; Imbach, J.-L. A New Synthesis of Some 4′-Thio-D-Ribonucleosides and Preliminary Enzymatic Evaluation. Nucleosides Nucleotides 1994, 13, 2035-2050.
5. Dukhan, D.; De Valette, F.; Marquet, R.; Ehresman, B.; Ehresman C.; Morvan, F.; Barascut, J.-L.; Imbach, J.-L. 4′-Thio-RNA: Synthesis, Base Pairing Properties and Interaction with Dimerization Initiation Site of HIV-1. Nucleosides Nucleotides 1999, 18, 1423-1424.
6. Franchetti, P.; Cappellacci, L.; Abu Sheikha, G.; Jayaram, H. N.; Gurudutt, V. V.; Sint, T.; Schneider, B. P.; Jones, W. D.; Goldstein, B. M.; Perra, G.; De Montis A.; Loi, A. G.; La Colla, P.; Grifantini, M. Synthesis, Structure, and Antiproliferative Activity of Selenophenfurin, an Inosine 5′-Monophosphate Dehydrogenase Inhibitor Analogue of Selenazofurin. J. Med. Chem. 1997, 40, 1731-1737.
7. Jayaram, H. N.; Zhen, W.; Gharehbaghi, K. Biochemical Consequences of Resistance to Tiazofurin in Human Myelogenous Leukemia K562 Cells. Cancer. Res. 1993, 53, 2344-2348.
8. (a) Frisch et al. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
9. (b) Frisch, A. E.; Frisch, M. J. Gaussian 98 users reference, 2nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1998.
10. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions from a Natural Bond Orbital, Donor-acceptor Viewpoint. Chem. Rev. 1988, 88, 899-926.
11. Becke, A. D. Density-functional thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 1993, 98, 5648-5652.
12. Burling, F. T.; Goldstein, B. M. Computational Studies of Nonbonded Sulfur-oxygen and Selenium-oxygen Interactions in the Thiazole and Selenazole Nucleosides. J. Am. Chem. Soc., 1992, 114, 2313-2320.
13. Makara, G. M.; Keseru, G. M. On the Conformation of Tiazofurin Analogues. J. Med. Chem. 1997, 40, 4154-4159.
14. (a) Colby, T. D.; Vanderveen, K.; Strickler, M. D.; Markham, G. D.; Goldstein, B. M. Crystal Structure of Human Type II Inosine Monophosphate Dehydrogenase: Implications for Ligand Binding and Drug Design. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 3531-3536.
15. (b) Goldstein, B. M.; Colby, T. D. IMP Dehydrogenase: Structural Aspects of Inhibitor Binding. Curr. Med. Chem. 1999, 6, 519-536.
16. Cooney, D. A.; Wilson, Y.; McGee, E. A. Straightforward and radiomatric technique for measuring IMP dehydrogenase. Anal. Biochem. 1983, 130, 339-345.
17. Gharehbaghi, K.; Shreenath, A.; Hao, Z.; Paull, K. D.; Szekeres, T.; Cooney, D. A.; Krohn, K.; Jayaram, H. N. Comparison of biochemical parameters of benzamide riboside, a new inhibitor of IMP dehydrogenase, with tiazofurin and selenazofurin. Biochem. Pharmacol. 1994, 48, 1413-1419.