Nucleosides and nucleotides. 158. 1-(3-C-ethynyl-β-D-ribo- pentofuranosyl)-cytosine, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil, and their nucleobase analogues as new potential multifunctional antitumor nucleosides with a broad spectrum of activity

Journal of Medicinal Chemistry

Volumn 39, Issue 25, 1996, Pages 5005-5011

  Hattori, Hideshi ^a   Tanaka, Motohiro ^b   Fukushima, Masakazu ^c   Sasaki, Takuma ^b   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b KANAZAWA UNIVERSITY   (Japan)

^c TAIHO PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 C ETHYNYL BETA D RIBOPENTOFURANOSYL)CYTOSINE; 1 (3 C ETHYNYL BETA D RIBOPENTOFURANOSYL)URACIL; ADENINE DERIVATIVE; ANTINEOPLASTIC AGENT; CYTOSINE DERIVATIVE; FLUCYTOSINE; FLUOROURACIL DERIVATIVE; GUANINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; NUCLEOTIDE DERIVATIVE; THYMINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER GRAFT; CANCER INHIBITION; CELL STRAIN KB; CONTROLLED STUDY; DNA SYNTHESIS INHIBITION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INTRAVENOUS DRUG ADMINISTRATION; LEUKEMIA L 1210; MOUSE; NONHUMAN; NUDE MOUSE; POLYMERIZATION; RNA SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CYTIDINE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; URACIL; URIDINE;

EID: 0029731762     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960537g     Document Type: Article

References (34)

1. For part 157, see: Shuto, S.; Obara, T.; Yaginuma, S.; Matsuda, A. New Neplanocin Analogues. IX. A practical preparation of (6′R)-6′-C-methylneplanocin A (RMNPA), a potent antiviral agent, by the diastereoselective enzymatic deamination as a key-step, and the determination of Its 6′-configuration. Chem. Pharm. Bull., in press.
2. For a recent review, see: Cancer Chemotherapeutic Agents; Foye, W. D., Ed.; American Chemical Society: Washington, DC, 1995; Chapter 3, pp 47-109.
3. (a) Takenuki, K.; Matsuda, A.; Ueda, T.; Sasaki, T.; Fujii, A.; Yamagami, K. Design, synthesis, and antineoplastic activity of 2′-deoxy-2′-methylidenecytidine. J. Med. Chem. 1988, 31, 1063-1064.
4. (b) Matsuda, A.; Takenuki, K.; Sasaki, T.; Ueda, T. Synthesis of a new broad spectrum of antineoplastic nucleoside, 2′-deoxy-2′-methylidenecytidine (DMDC) and its derivatives. J. Med. Chem. 1991, 34, 812-819.
5. (c) Yamagami, K.; Fujii, A.; Arita, M.; Okumoto, T.; Sakata, S.; Matsuda, A.; Ueda, T.; Sasaki, T. Antitumor activity of 2′-deoxy-2′-methylidenecytidine. A new 2′-deoxycytidine derivative. Cancer Res. 1991, 51, 2319-2323.
6. (d) Lin, T.-S.; Luo, M. Z.; Liu, M. C.; Clarkatzenburg, R. H.; Cheng, Y. C.; Prusoff, W. H.; Mancini, W. R.; Birnbaum, G. I.; Gabe, E.; Giziewicz, J. Synthesis and anticancer and antiviral activities of various 2′- and S′-methylidene-substituted nucleoside analogues and crystal structure of 2′-deoxy-2′-methylidenecytidine hydrochloride. J. Med. Chem. 1991, 34, 2607-2615.
7. (e) Baker, C. H.; Banzon, J.; Bollinger, J. M.; Stubbe, J.; Samano, V.; Robins, M. J. 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.
8. (f) Cory, A. H.; Samano, V.; Robins, M. J.; Cory, J. G. 2′-Deoxy-2′-methylene derivatives of adenosine, guanosine, tubercidin, cytidine and uridine as inhibitors of L1210 cell growth in culture. Biochem. Pharmacol. 1994, 47, 365-371.
9. (g) Ono, T.; Fujii, A.; Yamagami, K.; Hosoya, M.; Okumoto, T.; Sakata, S.; Matsuda, A.; Sasaki, T. Cell kill kinetics of an antineoplastic nucleoside, 1-(2-deoxy-2-methylene-β-D-erythropentofuranosyl)cytosine. Biochem. Pharmacol. 1996, 52, 1279-1285.
10. Plunkett, W.; Huang, P.; Xu, Y.-Z.; Heinemann, V.; Grunewald, R.; Gandhi, V. Gemcitabine: Metabolism, mechanisms of action, and self-potentiation. Semin. Oncol. 1995, 22 (Suppl. 11), 3-10 and references cited therein.
11. (a) Matsuda, A.; Nakajima, Y.; Azuma, A.; Tanaka, M.; Sasaki, T. 2′-C-Cyano-2′-deoxy-l-β-D-arabinofuranosylcytosine (CNDAC): Design of a potential mechanism-based DNA-strand breaking antineoplastic nucleoside. J. Med. Chem. 1991, 34, 2917-2919.
12. (b) Azuma, A.; Nakajima, Y.; Nishizono, N.; Minakawa, N.; Suzuki, M.; Hanaoka, K.; Kobayashi, T.; Tanaka, M.; Sasaki, T.; Matsuda, A. 2′-C-Cyano-2′-deoxy-1-β-D-arabinofuranosylcytosine and its derivatives: A new class of nucleoside with a broad antitumor spectrum. J. Med. Chem. 1993, 36, 4183-4189.
13. (c) Tanaka, M.; Matsuda, A.; Terao, T.; Sasaki, T. Antitumor activity of a novel nucleoside, 2′-C-cyano-2′-deoxy-1-β-D-arabinofuranosylcytosine (CNDAC) against murine and human tumors. Cancer Lett. 1992, 64, 67-74.
14. (d) Azuma, A.; Hanaoka, K.; Kurihara, A.; Kobayashi, T.; Miyauchi, S.; Kamo, N.; Tanaka, M.; Sasaki, T.; Matsuda, A. Chemical stability of a new antitumor nucleoside, 2′-C-cyano-2′-deoxy-1-β-D-arabinio-pentofuranosylcytosine (CNDAC) in alkaline medium: Formation of 2′-C-cyano-2′-deoxy-1-β-D-ribo-pentofuranosylcytosine (CNDC) and its antitumor activity. J. Med. Chem. 1995, 38, 3391-3397.
15. (e) Matsuda, A.; Azuma, A. 2′-C-Cyano-2′-deoxy-1-β-D-arabinofuranosylcytosine (CNDAC): A mechanism-based DNA-strand-breaking antitumor nucleoside. Nucleosides Nucleotides 1995, 14, 461-471.
16. (a) Thelander, L.; Reichard, P. Reduction of ribonucleotides. Ann. Rev. Biol. 1979, 48, 133-158.
17. (b) Inhibitors of Ribonucleoside Diphosphate Reductase Activity; Cory, J. G., Cory, A. H., Eds.; Pergamon Press: New York, 1989.
18. Ling, J.; Sahlin, M.; Sjoberg, B.; Loehr, T. M.; Sanders-Loehr, J. Dioxygen is the source of the μ-oxo bridge in iron ribonucleotide reductase. J. Biol. Chem. 1994, 269, 5595-5601.
19. Stubbe, J.; Ackles, D. On the mechanism of ribonucleoside diphosphate reductase from Escherichia coli. J. Biol. Chem. 1980, 255, 8027-8030.
20. Mao, S. S.; Holler, T. P.; Bollinger, J. M., Jr.; Yu, G. X.; Johnston, M. I.; Stubbe, J. A model for the role of multiple cysteine involved in ribonucleotide reduction: Amazing and still confuzing. Biochemistry 1992, 31, 9733-9743.
21. Uhlin, U.; Eklund, H. Structure of ribonucleotide reductase protein R1. Nature 1994, 370, 533-539.
22. (a) Broka, C. A.; Reichert, D.E. Thiophenol promoted cyclization of enynes. Tetrahedron Lett. 1987, 28, 1503-1506.
23. (b) Oswald, A. A.; Griesbaum, K.; Hundson, B. E. Organic sulfur compounds. XIII. Free-radical addition of thiols to phenylacetylene. J. Am. Chem. Soc. 1964, 86, 2877-2884.
24. Matsuda, A.; Hattori, H.; Tanaka, M.; Sasaki, T. 1-(3-C-Ethynyl-β-D-ribo-pentofuranosyl)uracil as a broad spectrum antitumor nucleoside. BioMed. Chem. Lett. 1996, 6, 1887-1892.
25. Yoshimura, Y.; Sano, T.; Matsuda, A.; Ueda, T. Synthesis of 6,3′-methanocytidine, 6,3′-methanouridine, and their 2′-deoxyribonucleosides. Chem. Pharm. Bull. 1988, 36, 162-167.
26. Bevierre, M.-O.; De Mesmaeker, A.; Wolf, R. M.; Freier, S. M. Synthesis of 2′-O-methyl-6,3′-ethanouridine and its introduction into antisense oligonucleotides. BioMed. Chem. Lett. 1994, 4, 237-240.
27. Nutt, R. F.; Dickinson, M. J.; Holly, F. W.; Walton, E. Branchedchain sugar nucleosides. III. 3′-C-Methyladenosine. J. Org. Chem. 1970, 33, 1789-1795.
28. Niedballa, U.; Vorbruggen, H. A general synthesis of N-glycosides. I. Synthesis of pyrimidine nucleosides. J. Org. Chem. 1974, 39, 3654-3660.
29. (a) Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ber. 1981, 114, 1234-1255.
30. (b) Vorbruggen, H.; Hofle, G. On the nucleoside synthesis. Chem. Ber. 1981, 114, 1256-1268.
31. Jung, P. M. J.; Burger, A.; Biellmann, J.-F. Rapid and efficient stereocontrolled synthesis of C-3′-ethynyl ribo and xylonucleosides by organocerium additions to 3′-ketonucleosides. Tetrahedron Lett. 1995, 36, 1031-1034 and references cited therein.
32. Paull, K. D.; Hamel, E.; Malspeis, L. Prediction of Biochemical Mechanism of Action from the In Vitro Antitumor Screen of the National Cancer Institute. In Cancer Chemotherapeutic Agents; Foye, W. O., Ed.; American Chemical Society: Washington, DC, 1995; pp 9-45.
33. Some of tha data were taken from ref 12.
34. Carmichael, J.; DeGraff, W. G.; Gazdar, A. F.; Minna, J. D.; Mitchell, J. B. Evaluation of a tetrazolium-based semiautomated colorimetric assay. Assessment of chemosensitivity testing. Cancer Res. 1987, 47, 936-942.