Synthesis of 2,5-bis(spirocyclohexane)-substituted nitroxides of pyrroline and pyrrolidine series, including thiol-specific spin label: An analogue of MTSSL with long relaxation time

Journal of Organic Chemistry

Volumn 77, Issue 18, 2012, Pages 8016-8027

  Kirilyuk, Igor A ^a   Polienko, Yuliya F ^a   Krumkacheva, Olesya A ^b   Strizhakov, Rodion K ^b   Gatilov, Yurii V ^a   Grigor'ev, Igor A ^a   Bagryanskaya, Elena G ^a,b  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b INTERNATIONAL TOMOGRAPHY CENTER   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON-SPIN RELAXATION; NITROXIDES; PENTADECANE; PYRROLIDINES; REDUCTION RATE; SITE-DIRECTED SPIN LABELING; SPECTRAL PROPERTIES; SPIN LABEL; TEMPERATURE DEPENDENCIES;

METHANE;

NITROGEN OXIDES;

ASCORBIC ACID; CYCLOHEXANE DERIVATIVE; METHANE; NITROXIDE DERIVATIVE; PYRROLIDINE DERIVATIVE; PYRROLINE DERIVATIVE; SULFONIC ACID DERIVATIVE; THIOL;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; FAVORSKII REARRANGEMENT; HYDROLYSIS; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION TIME; REDUCTION; SPIN LABELING; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE DEPENDENCE;

CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; MESYLATES; MOLECULAR STRUCTURE; NITRIC OXIDE; PYRROLES; PYRROLIDINES; SPIN LABELS; SPIRO COMPOUNDS; SULFHYDRYL COMPOUNDS;

EID: 84867705933     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301235j     Document Type: Article

References (61)

1. Tebben, L.; Studer, A. Angew. Chem, Int. Ed. 2011, 50, 5034-5068.
2. Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688.
3. Amabilino, D. B.; Veciana, J. Nitroxide-Based Organic Magnets, in Magnetism: Molecules to Materials II: Models and Experiments; Miller, J. S., Drillon, M., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2003; pp 1-60.
4. Ovcharenko, V. In Stable Radicals. Fundamentals and Applied Aspects of Odd-Electron Compounds; Hicks, R. G., Ed.; Wiley: Chichester, UK, 2010; pp 461-506.
5. Bobbitt, J. M.; Brückner, C.; Merbouh, N. Org. React. 2010, 103-424.
6. Khramtsov, V. V.; Zweier, J. L. In Stable Radicals. Fundamentals and Applied Aspects of Odd-Electron Compounds; Hicks, R. G., Ed.; Wiley: Chichester, UK, 2010; pp 537-566.
7. Khramtsov, V. V.; Grigor'ev, I. A.; Foster, M. A.; Lurie, D. J. Antioxid. Redox Signaling 2004, 6 (3), 667-676.
8. Likhtenshtein, G. I.; Yamauchi, J.; Nakatsuji, S.; Smirnov, A. I.; Tamura, R. Nitroxides: Applications in Chemistry, Biomedicine, and Materials Science; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2008; p 420.
9. Soule, B. P.; Hyodo, F.; Matsumoto, K.-I.; Simone, N. L.; Cook, J. A.; Krishna, M. C.; Mitchell, J. B. Free Radicals Biol. Med. 2007, 42 (11), 1632-1650.
10. Suga, T.; Nishide, H. In Stable Radicals. Fundamentals and Applied Aspects of Odd-Electron Compounds, Hicks, R. G., Ed.; Wiley: Chichester, UK, 2010; pp 507-520.
11. (a) Wetter, Ch.; Gierlich, J.; Knoop, Ch.A.; Mëller, Ch.; Schulte, T.; Studer, A. Chem.-Eur. J. 2004, 10, 1156-1166.
12. (b) Miura, Y.; Nakamura, N.; Taniguchi, I. Macromolecules 2001, 34 (3), 447-455.
13. Marx, L.; Chiarelli, R.; Guiberteau, T.; Rassat, A. J. Chem. Soc., Perkin Trans. 1 2000, 1181-1182.
14. Kirilyuk, I. A.; Bobko, A. A.; Grigor'ev, I. A.; Khramtsov, V. V. Org. Biomol. Chem. 2004, 2, 1025-1030.
15. Okazaki, S.; Mannan, M. A.; Sawai, K.; Masumizu, T.; Miura, Y.; Takeshita, K. Free Radical Res. 2007, 41 (10), 1069-1077.
16. Kinoshita, Yu.; Yamada, K.; Yamasaki, T.; Sadsue, H.; Sakai, K.; Utsumi, H. Free Radical Res. 2009, 43 (6), 565-571.
17. Yamasaki, T.; Mito, F.; Ito, Y.; Pandian, S.; Kinoshita, Y.; Nakano, K.; Murugesan, R.; Sakai, K.; Utsumi, H.; Yamada, K. J. Org. Chem. 2011, 76 (2), 435-440.
18. Rajca, A.; Kathirvelu, V.; Roy, S. K.; Pink, M.; Rajca, S.; Sarkar, S.; Eaton, S. S.; Eaton, G. R. Chem.-Eur. J. 2010, 16 (19), 5778-5782.
19. Kathirvelu, V.; Smith, C.; Parks, C.; Mannan, M. A.; Miura, Y.; Takeshita, K.; Eaton, S. S.; G. Eaton, R. Chem. Commun. 2009, 454-456.
20. Keana, J. F. W.; Pou, S.; Rosen, G. M. Magn. Reson. Med. 1987, 5, 525-536.
21. Rozantsev, E. G. Free Nitroxyl Radicals; Ulrich, H., Ed.; Plenum Press: New York, 1970; p 249 (translated from Russian by B. J. Hazzard).
22. Sosnovsky, G.; Cai, Z. J. Org. Chem. 1995, 60 (11), 3414-3418.
23. Krinitskaya, L. A.; Kissin, Yu. V.; Solov'eva, A. B. J. Appl. Spectrosc. 1977, 27, 1539-1543.
24. Sadtler Standard Carbon-13 Spectra; Sadtler Research Laboratories, Division of Bio-Rad Laboratories, Inc., Sadtler: Philadelphia, PA, 1979; Vol. 39, p 7656C.
25. Nuclear Magnetic Resonance Spectra, Sadtler Research Laboratories, Inc., Sadtler: Philadelphia, PA, 1974; Vol. 29, p 19330M.
26. Edeleva, M.; Marque, S. R. A.; Bertin, D.; Gigmes, D.; Guillaneuf, Y.; Morozov, S.; Bagryanskaya, E. G. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 6828-6842.
27. Murayama, K.; Yoshioka, T. Bull. Chem. Soc. Jpn. 1969, 42, 1942-47.
28. Hankovszky, H. O.; Hideg, K.; Tigyi, J. Acta Chim. Acad. Sci. Hung. 1978, 98, 339-348.
29. Hideg, K.; Hankovsky, O. H. In Biological Magnetic Resomnance. V. 8, Spin Labeling. Theory and Applications. Berliner, L. J., Reuben, J., Ed.; Plenum Press: New York, 1989; pp 427-488.
30. Keana, J. F. W.; Van Nice, F. L. Physiol. Chem. Phys. Med. NMR 1984, 16, 477-480.
31. Mathew, A. E.; Dodd, J. R. J. Heterocycl. Chem. 1985, 22, 225-228.
32. Hideg, K.; Hankovszky, H. O.; Halász, H. A.; Sohár, P. J. Chem. Soc., Perkin Trans. 1 1988, 2905-2911.
33. Nuclear Magnetic Resonance Spectra; Sadtler Research Laboratories, Inc., Sadtler: Philadelphia, PA, 1974; Vol. 14, p 8716M.
34. Campagna, F.; Carotti, A.; Casini, G. Tetrahedron Lett. 1977, 21, 1813-1816.
35. Miyake, M.; Shen, J.; Liu, S.; Shi, H.; Liu, W.; Yuan, Z.; Pritchard, A.; Kao, J. P. Y.; Liu, K. J.; Rosen, G. M. J. Pharmacol. Exp. Ther. 2006, 318, 1187-1193.
36. Keana, J. F. W.; Hideg, K.; Birell, G. B.; Hankovszky, O. H.; Ferguson, G.; Parvez, M. Can. J. Chem. 1982, 60, 1439-1447.
37. Chatani, S.; Nakamura, M.; Akahane, H.; Kohyama, N.; Taki, M.; Arata, T.; Yamamoto, Y. Chem. Commun. 2005, 1880-1882.
38. Yan'shole, V. V.; Kirilyuk, I. A.; Grigor'ev, I. A.; Morozov, S. V.; Tsentalovich, Yu. P. Russ. Chem. Bull. 2010, 59 (1), 66-74.
39. Bobko, A. A.; Kirilyuk, I. A.; Gritsan, N. P.; Polovyanenko, D. N.; Grigor'ev, I. A.; Khramtsov, V. V.; Bagryanskaya, E. G. Appl. Magn. Reson. 2010, 39, 437-451.
40. Hyde, J. S.; Subczynski, W. K. J. Magn. Reson. 1984, 56, 125-130.
41. (a) Milov, A. D.; Salikhov, K. M.; Shirov, M. D. Fiz. Tverd. Tela 1981, 23, 975-982.
42. (b) Milov, A. D.; Maryasov, A. G.; Tsvetkov, Y. D. Appl. Magn. Reson. 1998, 15, 107-143.
43. Zecevic, A.; Eaton, G. R; Eaton, S. S.; Lindgren, M. Mol. Phys. 1998, 95 (6), 1255-1263.
44. Miyake, M.; Shen, J.; Liu, S.; Shi, H.; Liu, W.; Yuan, Z.; Pritchard, A.; Kao, J. P. Y.; Liu, K. J.; Rosen, G. M. J. Pharmacol. Exp. Ther. 2006, 318, 1187-1193.
45. Richard Ward, R.; Bowman, A.; Sozudogru, E.; El-Mkami, H.; Owen-Hughes, T.; Norman, D. G. J. Magn. Reson. 2010, 207, 164-167.
46. Hagelueken, G.; Ingledew, W. J.; Huang, H.; Petrovic- Stojanovska, B.; Whitfield, C.; ElMkami, H.; Schiemann, O.; Naismith, J. H. Angew. Chem., Int. Ed. Engl. 2009, 48, 2904-2906.
47. Reginsson, G. W.; Schiemann, O. Biochem. J. 2011, 434, 353-363.
48. Bode, B. E.; Dastvan, R.; Prisner, T. J. Magn. Reson. 2011, 211, 11-17.
49. Dastvan, R.; Bode, B. E.; Karuppiah, M.; Marko, A.; Lyubenova, S.; Schwalbe, H.; Prisner, T. J. Phys. Chem. B 2010, 114, 13507-13516.
50. Endeward, B.; Butterwick, J. A.; MacKinnon, R.; Prisner, T. F. J. Am. Chem. Soc. 2009, 131, 15246-15250.
51. Denysenkov, V. P.; Biglino, D.; Lubitz, W.; Prisner, T. F.; Bennati, M. Angew. Chem., Int. Ed 2008, 47, 1224-1227.
52. Jeschke, G.; Polyhach, Y. Phys. Chem. Chem. Phys. 2007, 9, 1895-1910.
53. Zhou, Y.; Bowler, B. E.; Eaton, G. R.; Eaton, S. S. J. Magn. Reson. 1999, 139, 165-174.
54. Cowie, J. M. G.; Toporowski, P. M. Can. J. Chem. 1961, 39, 2240-2243.
55. Kocherginsky, N.; Swarts, H. M. Nitroxide Spin Labels. Reactions in Biology and Chemistry; CRC Press: Boca Raton, FL, 1995; p 270.
56. Bobko, A. A.; Kirilyuk, I. A.; Grigor'ev, I. A.; Zweier, J. L.; Khramtsov, V. V. Free Radicals Biol. Med. 2007, 42, 404-412.
57. Vianello, F.; Momo, F.; Scarpa, M.; Rigo, A. Magn. Reson. Imaging 1995, 13 (2), 219-226.
58. Krstic, I.; Hänsel, R.; Romainczyk, O.; Engels, J. W.; Dötsch, V.; Prisner., T. Angew. Chem., Int. Ed. 2011, 50, 5070-5074.
59. Igarashi, R; Sakai, T; Hara, H; Tenno, T; Tanaka, T; Tochio, H; Shirakawa, M. J. Am. Chem. Soc. 2010, 132, 8228-8229.
60. Azarkh, M; Okle, O; Singh, V; Seemann, I. T.; Hartig, J. S.; Dietrich, D. R.; Drescher, M. ChemBioChem 2011, 12, 1992-1995.
61. Miura, Y.; Nakamura, N.; Taniguchi, I. Macromolecules 2001, 34 (3), 447-455.