5-Fluorouracil derivatives. 1. Acyclonucleosides through a tin (IV) chloride-mediated regiospecific ring opening of alkoxy-1,4-diheteroepanes

Tetrahedron

Volumn 52, Issue 26, 1996, Pages 8907-8924

  Campos, J ^a   Pineda, M J ^a   Gomez J A ^a   Entrena, A ^a   Trujillo, M A ^a   Gallo, M A ^a   Espinosa, A ^a  

^a Facultad de Farmacia   (Spain)

Author keywords

1,4 diheteroepanes; 5 Fluorouracil; Acyclonucleosides; Antitumour agents; Regiospecificity

Indexed keywords

1 [[3 (2 HYDOXYETHOXY) 1 CYCLOPENTOXY]PROPYL] 5 FLUOROURACIL; ACYCLIC NUCLEOSIDE; FLUOROURACIL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TUMOR CELL; X RAY ANALYSIS;

ANIMALIA;

EID: 0029952618     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00439-5     Document Type: Article

References (48)

1. Schaeffer, H. J., Beauchamp, L.; De Miranda, P.; Elion, G. B.; Bauer, D. J., Collins, P. Nature, 1978, 272, 583.
2. (a) Chu, C. K.; Cutler, S. J. Heterocyclic Chem., 1986, 23, 289;
3. (b) Chu, C. K.; Baker, D. C. Nucleosides and Nucteotides as Antitumor and Antiviral Agents; Plenum Press: New York, 1993.
4. Beauchamp, L. M.; Serling, B. L.; Kelsey, J. E.; Biron, K. K.; Collins, P.; Selway, J.; Lin, J.-C.; Schaeffer, H. J. J. Med. Chem., 1988, 31, 144.
5. Kelley, J. L.; Kelsey, J. E.; Hall, W. R.; Krochmal M. P.; Shaeffer, H. J. J. Med. Chem., 1981, 24, 753.
6. Ajmera, S.; Bapat, A. R.; Stephanian, E.; Danenberg, P. V. J. Med. Chem., 1988, 31, 1094.
7. Hasan, A.; Srivastava, P. C. J. Med. Chem., 1992, 32, 1435.
8. (a) Robins, M. J.; Hatfield, P. W. Can. J. Chem., 1982, 60, 547;
9. (b) Tyms, A. S.; Kenny M.; Navé, J.-F. Bioorg. Med. Chem. Lett., 1995, 5, 1275.
10. Ubasawa, M.; Takashima, H.; Sekiya, K. Chem. Pharm. Bull., 1995, 43, 142.
11. (a) Houston D. M.; Dolence, E. K.; Keller, B. T.; Patel-Thombre, U.; Borchardt, R. T. J. Med. Chem., 1985, 28, 471;
12. (b) Beaton, G.; Jones, A. S.; Walker, R. T. Tetrahedron, 1988, 44, 6419.
13. Scheiner, P.; Geer, A.; Bucknor A.-M.; Imbach, J.-L.; Schinazi, R. F. J. Med. Chem., 1989, 32, 73.
14. (a) Vorbrüggen, H.; Bennua, B. Chem. Ber., 1981, 114, 1279;
15. (b) Hilbert, G. E.; Johnson, T. B. J. Am. Chem. Soc., 1930, 52, 4489;
16. Ueda, T.; Nishino, H. J. Am. Chem. Soc., 1968, 90, 1678.
17. Tietze, L. F.; Krach, T.; Beller, M.; Arlt, M. Chem. Ber., 1991, 124, 2019.
18. Farquhar, D.; Chen, R.; Khan, S. J. Med. Chem., 1995, 38, 488.
19. 1a-b cristallize after standing in vacua in a desiccator for a long period of time, such as two or three months.
20. For a preliminary account of this work, see: (a) Gallo, M. A.; Espinosa, A.; Campos, J.; Entrena, A.; Domínguez, J. F.; Camacho, E.; Pineda, M. J.; Gómez, J. A. Synlett, 1993, 6, 389;
21. (b) Gallo, M. A.; Espinosa, A.; Campos, J.; Entrena, A.; Pineda, M. J.; Gómez, J. A. II Farmaco, 1995, 50, 395;
22. Universidad de Granada, Eur. Pat. Appl. WO 91 17,147 (Cl. CO7D239/54); via Chem. Abstr. 1992, 117, 49156d.
23. King, B. Encyclopedia of Inorganic Chemistry, John Wiley & Sons, New York, 1994; pp. 4159-4197.
24. Choi, W.-B.; Wilson, L. J.; Yeola, S.; Liotta, D. C.; Schinazi, R. F. J. Am. Chem. Soc., 1991, 113, 9377
25. Wilson, L. J.; Hager, M. W. El-Kattan, Y. A.; Liotta, D. C. Synthesis, 1995, 1465.
26. 2O as an effective catalyst for nucleoside formation, see: Niedballa, U.; Vorbrüggen, H. J. Org. Chem., 1974, 39, 3654.
27. Vorbrüggen, H.; Höfle, G. Chem. Ber., 1981, 114, 1256.
28. March, J., Advanced Organic Chemistry, John Wiley & Sons, New York, 1992; p. 261.
29. It has to be noted that the alkoxy-1,4-diheteroepanes 1a-g are very volatile substances, although such saturated heterocycles were isolated by distillation under diminished pressure (bp's ranging from 45 to 70 °C/16 torr). After purification by flash chromatography, much care has to be taken on rotaevaporating off the eluant (ether/hexane mixtures) and the water bath must not be warmed at all. Actually, only five minutes in the desiccator under vacum is recommended in order to avoid losses of the materials. Microanalyses were not carried out on these cycloacetals due to the impossibility of stabilizing the weights. Nevertheless the NMR spectra always showed sample homogeneities
30. Espinosa, A.; Gallo, M. A.; Campos, J. An. Quim., 1983, 79C, 210.
31. Espinosa, A.; Gallo, M. A.; Campos, J.; Gómez, J. A. Synlett, 1995, 11, 1119
32. Espinosa, A.; Gallo, M. A.; Campos, J. An. Quim., 1982, 78C, 232.
33. Espinosa, A.; Gallo, M. A.; Campos, J.; Entrena, A. Bull. Soc. Chim. Fr., 1987, 2, 379.
34. Espinosa, A.; Entrena, A., Gallo, M. A., Campos, J.; Domínguez, J F., Camacho, E.; Sánchez, I. J. Org. Chem., 1990, 55, 6018.
35. Clark, M.; Cramer, R. D.; Vann Opdenbosch, N J. Comput. Chem., 1989, 10, 982.
36. Sybyl Molecular Modelling; Tripos Associates, Inc.: St. Louis, MO
37. Gasteiger, J.; Marsili, M. Tetrahedron, 1980, 36, 3219.
38. Powell, M. J. D. Mathematical Programming, 1977, 12, 241.
39. This surprising conformational behaviour is due to a poor parametrization of the Tripos force field when we attempt to reproduce the gauche effect of the O-C-C-O fragment.
40. Hager, M. W.; Liotta, D. C. J. Am. Chem. Soc., 1991, 113, 5117.
41. Osaki, S.; Watanabe, Y.; Hoshiko, t.; Nagase, T.; Ogasawara, T.; Furukawa, H.; Llemura, A.; Ishikawi, K.; Mon, H.; Hoshi, A.; Iigo, M., Tokuzen, R. Chem. Pharm. Bull., 1986, 34, 150.
42. McCormick, J. E.; McElhinney, R. S. J. Chem. Research (M), 1983, 1736.
43. Bellringer, F. J.; Bewley, T. Brit. P. 713,833, 1954; via Chem. Abstr., 1958, 50, 6501c.
44. Bellringer, F. J.; Bewley, T. Brit. P. 713,833, 1954; via Chem. Abstr., 1958, 50, 6501c.
45. Piasecki, A. Tetrahedron, 1984, 40, 4893.
46. When the reaction time was shortened to 39 h, the mixture of trans- and cis-1d (trans cis ratio: 77/23 determined by glc) was obtained in 23.1% yield. No 2-(3-isopropoxy-2-propyl)-1,3-dioxolane was detected.
47. Faass, U.; Hilgert, H. Chem. Ber., 1954, 87, 1343.
48. Beudokian, P. Z. J. Am. Chem. Soc., 1944, 66, 651.