Synthesis of 1-pyrroline 1-oxides analogous to pseudouridine

Tetrahedron Letters

Volumn 52, Issue 16, 2011, Pages 1866-1870

  Koszytkowska Stawińska, Mariola ^a   Mironiuk Puchalska, Ewa ^a   Sas, Wojciech ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

1 Pyrroline 1 oxides; C Nucleoside analogues; Nitrones; Pseudouridine; Spin traps

Indexed keywords

1 AZA 7,14 DIOXADISPIRO[4.2.5.2]PENTADEC 1 ENE 1 OXIDE; GRIGNARD REAGENT; PSEUDOURIDINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DIMERIZATION; NONHUMAN; OXIDATION; SYNTHESIS;

EID: 79952739309     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.018     Document Type: Article

References (87)

1. Charette, M.; Gray, M. W. IUBMB Life 2000, 49, 341.
2. (a) Yoshikawa, T.; Kimura, S.; Hatano, T.; Okamoto, K.; Hayatsu, H.; Arimoto-Kobayshi, S. Food Chem. Toxicol. 2002, 40, 1165;
3. (b) Monobe, M.; Arimoto-Kobayashi, S.; Ando, K. Mutat. Res. 2003, 538, 93.
4. (a) Yokoyama, M.; Ikeue, T.; Ochiai, Y.; Momotake, A.; Yamaguchi, K.; Togo, H. J. Chem. Soc., Perkin Trans. 1 1998, 2185;
5. (b) Momotake, A.; Togo, H.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1999, 1193;
6. (c) Yokoyama, M.; Ikenogami, T.; Togo, H. J. Chem. Soc., Perkin Trans. 1 2000, 2067;
7. (d) Häberli, A.; Leumann, C. J. Org. Lett. 2001, 3, 489;
8. (e) Häberli, A.; Leumann, C. J. Org. Lett. 2002, 4, 3275;
9. (f) Häberli, A.; Mayer, A.; Leumann, C. J. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 1187;
10. (g) Marczak, R.; Hoang, V. T.; Noworyta, K.; Zandler, M. E.; Kutner, W.; D'Souza, F. J. Mater. Chem. 2002, 12, 2123;
11. (h) D'Souza, F.; Gadde, S.; Islam, D. M. S.; Pang, S. C.; Schumacher, A. L.; Zandler, M. E.; Horie, R.; Araki, Y.; Ito, O. Chem. Commun. 2007, 480;
12. (i) Sørensen, M. D.; Khalifa, N. M.; Pedersen, E. B. Synthesis 1999, 1937;
13. (j) Filichev, V. V.; Pedersen, E. B. Tetrahedron 2001, 57, 9163;
14. (k) Kim, D. C.; Yoo, K. H.; Kim, D. J.; Chung, B. Y.; Park, S. W. Tetrahedron Lett. 1999, 40, 4825;
15. (l) Romero, F. A.; Du, W.; Hwang, I.; Rayl, T. J.; Kimball, F. S.; Leung, D.; Hoover, H. S.; Apodaca, R. L.; Breitenbucher, J. G.; Cravatt, B. F.; Boger, D. L. J. Med. Chem. 2007, 50, 1058;
16. (m) Coutouli-Argyropoulou, E.; Lianis, P.; Mitakou, M.; Giannoulis, A.; Nowak, J. Tetrahedron 2006, 62, 1494;
17. (n) Chiacchio, U.; Corsaro, A.; Mates, J.; Merino, P.; Piperno, A.; Rescifina, A.; Romeo, G.; Romeo, R.; Tejero, T. Tetrahedron 2003, 59, 4733;
18. (o) Mertes, M. P.; Patel, N. R. J. Med. Chem. 1966, 9, 868;
19. (p) Inaba, A.; Inami, K.; Kimoto, Y.; Yanada, R.; Miwa, Y.; Taga, T.; Bessho, K. Chem. Pharm. Bull. 1995, 43, 1601;
20. (q) Fish, P. V.; Allan, G. A.; Bailey, S.; Blagg, J.; Butt, R.; Collis, M. G.; Greiling, D.; James, K.; Kendall, J.; McElroy, A.; McCleverty, D.; Reed, C.; Webster, R.; Whitlock, G. A. J. Med. Chem. 2007, 50, 3442.
21. Bailey, N.; Bamford, M. J.; Brissy, D.; Brookfield, J.; Demont, E.; Elliott, R.; Garton, N.; Farre-Gutierrez, I.; Hayhow, T.; Hutley, G.; Naylor, A.; Panchal, T. A.; Seow, H.-X.; Spalding, D.; Tale, A. Bioorg. Med. Chem. Lett. 2009, 19, 3602.
22. (a) Davies, M. J. In Electron Paramagnetic Resonance; Gilbert, B. C., Davies, M. J., Murphy, D. M., Eds.; The Royal Society of Chemistry, 2002; Vol. 18, pp 47-73;
23. (b) Fréjaville, C.; Karoui, H.; Tuccio, B.; Le Moigne, F.; Culcasi, M.; Pietri, S.; Lauricella, R.; Tordo, P. J. Med. Chem. 1995, 38, 258;
24. (c) Zhao, H.; Joseph, J.; Fales, H. M.; Sokoloski, E. A.; Levine, R. L.; Vasquez-Vivar, J.; Kalyanaraman, B. PNAS 2005, 102, 5727;
25. (d) Zhang, H.; Joseph, J.; Vasquez-Vivar, J.; Karoui, H.; Nsanzumuhire, C.; Martásek, P.; Tordo, P.; Kalyanaraman, B. FEBS Lett. 2000, 473, 58.
26. Stolze, K.; Rohr-Udilova, N.; Hofinger, A.; Rosenau, T. Bioorg. Med. Chem. 2009, 17, 7572.
27. (a) Floyd, R. A.; Hensley, K.; Forster, M. J.; Kelleher-Anderson, J. A.; Wood, P. L. Ann. N.Y. Acad. Sci. 2002, 959, 321;
28. (b) Maples, K. R.; Green, A. R.; Floyd, R. A. CNS Drugs 2004, 18, 1071;
29. (c) Floyd, R. A.; Kopke, R. D.; Choi, C.-H.; Foster, S. B.; Doblas, S.; Towner, A. T. Free Radical Biol. Med. 2008, 45, 1361;
30. (d) Sun, Y.; Jiang, J.; Zhang, Z.; Yu, P.; Wang, L.; Xu, C.; Liu, W.; Wang, Y. Bioorg. Med. Chem. 2008, 16, 8868;
31. (e) Piccinini, F.; Bradamante, S.; Monti, L.; Zhang, Y.-K.; Janzen, E. G. Free Radical Res. 1995, 23, 81.
32. McGee, S. A.; Wiggins, S. A.; Pierce, J. D. Int. J. Adv. Nurs. Pract. 2003, 6, 1523-6064.
33. (a) Krishna, M. C.; DeGraff, W.; Hankovszky, O. H.; Sár, C. P.; Kálai, T.; Jeckö, J.; Russo, A.; Mitchell, J. B.; Hideg, K. J. Med. Chem. 1998, 41, 3477;
34. (b) Gadajeva, V.; Lazarova, G.; Zheleva, A. Toxicol. Lett. 2003, 144, 289;
35. (c) Jin, Y.; Chen, S.-W.; Tian, X. Bioorg. Med. Chem. 2006, 14, 3062;
36. (d) Zhang, J.-Q.; Zhang, Z.-W.; Hui, L.; Chen, S.-W.; Tian, X. Bioorg. Med. Chem. Lett. 2010, 20, 983.
37. Goldstein, S.; Lestage, P. Curr. Med. Chem. 2000, 7, 1255.
38. Giner-Sonolla, A.; Zimmerman, I.; Beudich, A. J. Am. Chem. Soc. 1959, 81, 2515.
39. Tronchet, J. M. J.; Benhamza, R.; Dolatshashi, N.; Geoffroy, M.; Türler, H. Nucleosides Nucleotides 1988, 7, 249.
40. Maurel, V.; Rabant, J.-L.; Gambarelli, S. Rapid Commun. Mass Spectrom. 2006, 20, 2235.
41. (a) Tronche, C.; Goodman, B. K.; Greenberg, M. M. Chem. Biol. 1998, 5, 263;
42. (b) Chatgilialoglu, C.; Ferreri, C.; Bazzanini, R.; Guerra, M.; Choi, S.-Y.; Emanuel, C. J.; Horner, J. H.; Newcomb, M. J. Am. Chem. Soc. 2000, 122, 9525.
43. (a) Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Synlett 2000, 442;
44. (b) Lombardo, M.; Trombini, C. Synthesis 2000, 759;
45. (c) Grigor'ev, I. A. In Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis: Novel Strategies in Synthesis; Feuer, H., Ed., 2nd ed.; John Wiley & Sons, Inc., 2008; pp 129-434.
46. (a) Murahashi, S.-I.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736;
47. (b) Holzapfel, C. W.; Crous, R. Heterocycles 1998, 48, 1337;
48. (c) Merino, P.; Revuelta, J.; Tejero, T.; Cicchi, S.; Goti, A. Eur. J. Org. Chem. 2004, 776.
49. (a) Shapiro, R.; Chambers, R. W. J. Am. Chem. Soc. 1961, 83, 3920;
50. (b) Asbun, W.; Binkley, S. B. J. Org. Chem. 1966, 31, 2215;
51. (c) Asbun, W.; Binkley, S. B. J. Org. Chem. 1968, 31, 140;
52. (d) Lerch, U.; Burdon, M. G.; Mofatt, J. G. J. Org. Chem. 1971, 36, 1507;
53. (e) Bridges, S. D.; Brown, D. M.; Ogden, R. C. J. Chem. Soc., Chem. Commun. 1977, 460;
54. (f) Brown, D. M.; Ogden, R. C. J. Chem. Soc., Perkin Trans. 1 1981, 723;
55. (g) Grohar, P. J.; Chow, C. S. Tetrahedron Lett. 1999, 40, 2049;
56. (h) Hanessian, S.; Machaalani, R. Tetrahedron Lett. 2003, 44, 8321.
57. Koszytkowska-Stawińska, M.; Sas, W.; Sowińska, A. J. Chem. Res. (S) 1996, 162.
58. (a) Clément, J.-L.; Finet, J.-P.; Fréjaville, C.; Tordo, P. Org. Biomol. Chem. 2003, 1, 1591;
59. (b) Bardelang, D.; RockenBaure, A.; Karoui, H.; Finet, J.-P.; Biskupska, I.; Banaszak, K.; Tordo, P. Org. Biomol. Chem. 2006, 4, 2874;
60. (c) Stolze, K.; Rohr-Udilova, N.; Hofinger, A.; Rosenau, T. Bioorg. Med. Chem. 2008, 16, 8082.
61. For a very detailed review on the preparation and reactivity of nitrones, see: Ref. 15c.
62. Barbati, S.; Clément, J.-L.; Fréjaville, C.; Bouteiler, J. C.; Tordo, P.; Michel, J. M.; Yadan, J. C. Synthesis 1999, 2036.
63. + 370.1117, found 370.1121.
64. (a) Lhassani, M.; Chavignon, O.; Chezal, J. M.; Teulade, J. C.; Chapat, J. P.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E.; Gueiffier, A. Eur. J. Med. Chem. 1999, 34, 271;
65. (b) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Satake, M.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 11893.
66. 4). The volatiles were removed by distillation. Crystallization of the residue (hexane/AcOEt) gave 3 (485 mg, 75%) as a white solid (mp 124-126°C). The NMR spectra were consistent with those described in Ref. 18.
67. (a) Langley, B. W. J. Am. Chem. Soc. 1956, 78, 2136;
68. (b) Whale, R. F.; Coe, P. L.; Walker, R. T. Nucleosides Nucleotides 1992, 11, 1425.
69. (a) Bruni, P.; Giorgioni, E.; Tommasi, G.; Greci, L. Tetrahedron 1998, 54, 5305;
70. (b) Marco, J. A.; Carda, M.; Murga, J.; Portolés, R.; Falomir, E.; Lex, J. Tetrahedron Lett. 1998, 39, 3237.
71. (a) Bonnett, R.; Brown, R. F. C.; Clark, V. M.; Sutherland, I. O.; Todd, A. J. Chem. Soc. 1959, 2094;
72. (b) Lee, T. D.; Keana, J. F. W. J. Org. Chem. 1978, 43, 4226;
73. (c) Keana, J. F. W.; Seyedrezai, S. E.; Gaughan, G. J. Org. Chem. 1983, 48, 2644;
74. (d) Bárácz, N. M.; Hankowszky, O. P.; Sár, C. P.; Jerkovich, G.; Hideg, K. Synthesis 1996, 204.
75. +) 363.1794, found 363.1812. The NMR spectra of 10 were consistent with those described: Pelissier, H.; Rodriguez, J.; Volhardt, K. P. C. Chem. Eur. J. 1999, 5, 3549.
76. (a) Brown, R. F. C.; Clark, V. M.; Lamchen, M.; Todd, A. J. Chem. Soc. 1959, 2116;
77. (b) Brown, R. F. C.; Clark, V. M.; Todd, A. J. Chem. Soc. 1965, 2337;
78. (c) Boocock, D. G.; Darcey, B. R.; Ullman, E. F. J. Am. Chem. Soc. 1968, 90, 5945;
79. (d) Voinov, M. A.; Grigor'ev, I. A.; Volodarsky, L. B. Heterocycl. Commun. 1998, 4, 261.
80. Voinov, M. A.; Grigor'ev, I. A. Russ. Chem. Bull. Int. Ed. 2002, 51, 279.
81. For generation of the 2,4-dimethoxypyrimidine-Grignard reagent by halogen-metal exchange, see Ref. 3b.
82. 2 could play a similar role as LiCl in the preparation of Grignard reagents from both arylmagnesium chlorides and bromides, see: (a) Piller, F. M.; Metzger, A.; Schade, M. A.; Hagg, B. A.; Gavryushin, A.; Knochel, P. Chem. Eur. J. 2009, 15, 7192;
83. (b) Yamada, S.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2010, 49, 2215.
84. 3/acetone, 85/15, v/v) gave 10 (126 mg, 39%) and 11 (197 mg, 36%, mp 151-152°C).
85. +) 331.1783, found 331.1780.
86. +) 255.0855, found 255.0853.
87. +) 283.1168, found 283.1172.