Synthesis, structure, and X-band (9.5 GHz) EPR characterization of the new series of pH-sensitive spin probes: N,N-disubstituted 4-amino-2,2,5,5- tetramethyl-3-imidazoline 1-oxyls

Journal of Organic Chemistry

Volumn 70, Issue 24, 2005, Pages 9702-9711

  Voinov, Maxim A ^b   Polienko, Julya F ^a,c   Schanding, Thomas ^d   Bobko, Andrey A ^e   Khramtsov, Valery V ^e,f   Gatilov, Yury V ^a   Rybalova, Tatyana V ^a   Smirnov, Alex I ^b   Grigor'ev, Igor A ^a,c  

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

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

^c NOVOSIBIRSK STATE UNIVERSITY   (Russian Federation)

^d Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

^e INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

^f OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ESTERS; PH EFFECTS; SYNTHESIS (CHEMICAL);

CARBOXYLIC GROUP; IMIDAZOLINE NITROXIDES;

PARAMAGNETIC RESONANCE;

4 AMINO 2,2,5,5 TETRAMETHYL 3 IMIDAZOLINE 1 OXYL DERIVATIVE; BROMOACETIC ACID; BUFFER; IMIDAZOLINE DERIVATIVE; NITROXIDE DERIVATIVE; OCTANOL; PHOSPHATE; POTASSIUM FERRICYANIDE; UNCLASSIFIED DRUG; WATER;

ALKYLATION; ARTICLE; ELECTRON SPIN RESONANCE; LIPOPHILICITY; PARTITION COEFFICIENT; PH MEASUREMENT; PKA; PROTON TRANSPORT; SUBSTITUTION REACTION; SYNTHESIS;

ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN-ION CONCENTRATION; IMIDAZOLINES; MOLECULAR STRUCTURE; X-RAY DIFFRACTION;

EID: 28144444935     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0510890     Document Type: Article

References (33)

1. (a) Khramtsov, V. V.; Weiner, L. M.; Grigor'ev, I. A.; Volodarsky, L. B. Chem. Phys. Lett. 1982, 91 (1), 69-72.
2. (b) Khramtsov, V. V.; Weiner, L. M.; Eremenko, S. I.; Belchenko, O. L; Schastnev, P. V.; Grigor'ev, I. A.; Reznikov, V. A. J. Magn. Reson. 1985, 61, 397-408.
3. (c) Khramtsov, V. V.; Vainer, L. M. Russ. Chem. Rev. 1988, 57 (9), 824-839.
4. (d) Clément, J.-L.; Barbati, S.; Fréjaville, C.; Rockenbauer, A.; Tordo, P. J. Chem. Soc., Perkin Trans. 2 2001, 1471-1475.
5. Keana, J. F. W.; Acarregui, M. J.; Boyle, S. L. M. J. Am. Chem. Soc. 1982, 104, 827-830.
6. (a) Balakirev, M.; Khramtsov, V. V. J. Chem. Soc., Perkin Trans. 2 1993, 2157-2160.
7. (b) Khramtsov, V. V.; Panteleev, M. V.; Weiner, L. M. J. Biochem. Biophys. Meth. 1989, 18, 237-246.
8. Khramtsov, V. V.; Marsh, D.; Weiner, L. M.; Reznikov, V. A. Biochim. Biophys. Acta 1992, 1104, 317-324.
9. (a) Molochnikov, L. S.; Kovalyova, E. G.; Grigor'ev, I. A.; Reznikov, V. A. Metal-Containing Polymeric Mater. 1996, 395-401.
10. (b) Molochnikov, L. S.; Kovalyova, E. G.; Lipunov, I. N.; Grigor'ev, I. A. Proc. Am. Chem. Soc. 1997, 77, 612-613.
11. (c) Molochnikov, L. S.; Kovalyova, E. G.; Grigor'ev, I. A.; Zagorodni, A. A. J. Phys. Chem. B 2004, 108, 1302-1313.
12. Khramtsov, V. V.; Grigor'ev, I. A.; Foster, M. A.; Lurie, D. J.; Nicholson, I. Cell. Mol. Biol. 2000, 46(8), 1361-1374.
13. Smirnov, A. I.; Ruuge, A.; Reznikov, V. A.; Voinov, M. A.; Grigor'ev, I. A. J. Am. Chem. Soc. 2004, 126, 8872-8873.
14. (a) Berezina, T. A.; Martin, V. V.; Volodarsky, L. B.; Khramtsov, V. V.; Weiner, L. M. Bioorg. Khim. 1990, 16, 262-269.
15. (b) Balakirev, M.; Khramtsov, V. V.; Berezina, T. A.; Martin, V. V.; Volodarsky, L. B. Synthesis 1992, 12, 1223-1225.
16. (c) Khramtsov, V. V.; Volodarsky, L. B. In Biological Magnetic Resonance, Vol. 14, Spin Labeling: The Next Millennium; Berliner, L. J., Ed.; Plenum Press: New York, 1998; pp 109-180.
17. Kirilyuk, I. A.; Shevelev, T. G.; Morozov, D. A.; Khromovskih, E. L.; Skuridin, N. G.; Khramtsov, V. V.; Grigor'ev, I. A. Synthesis 2003, 6, 871-878.
18. Khlestkin, V. K.; Tikhonov, A. Y. Heterocycl. Commun. 2002, 8 (3), 249-254.
19. Voinov, M. A.; Martin, V. V.; Volodarskii, L. B. Bull. Russ. Akad. Sci., Div. Chem. Sci. (Engl. Transl.) 1992, 41, 2091-2095.
20. Berezina, T. A.; Reznikov, V. A.; Volodarsky, L. B. Tetrahedron 1993, 49 (46), 10693-10704.
21. (a) Goerdeler, J.; Roth, W. Chem. Ber. 1963, 96 6(1-2), 534-549.
22. (b) Skipper, P. L.; Tannenbaum, S. R.; Baldwin, J. E.; Scott, A. Tetrahedron Lett. 1977, 49, 4269-4271.
23. (c) Fossey, J.; Loupy, A.; Strzelecka, E. Tetrahedron 1981, 37 (10-11), 1935-1941.
24. Rozantsev, E. G. Free Nitroxyl Radicals; Plenum: New York, 1970.
25. Smirnov, A. I.; Belford, R. L. J. Magn. Reson. A 1995, 98, 65-73.
26. Smirnova, T. I.; Smirnov, A. I.; Clarkson, R. B.; Belford, R. L. J. Phys. Chem. 1995, 99, 9008-9016.
27. Khramtsov, V. V.; Weiner, L. M. In Imidazoline Nitroxides; Vol. II, Applications; Volodarsky, L. B., Ed.; CRC Press: Boca Raton, FL, 1988; Chapter 2, p 42.
28. (a) Monaco, V.; Formaggio, F.; Crisma, M.; Toniolo, C.; Hanson, P.; Millhauser, G.; George, C.; Deschamps, J. R.; Flippen-Anderson, J. L. Bioorg. Med. Chum. 1999, 7, 119-131.
29. (b) Tominaga, M.; Barbosa, S. R.; Poletti, E. F.; Zukerman-Schpector, J.; Marchetto, R.; Schreier, S.; Paiva, A. C.; Nakaie, C. R. Chem. Pharm. Bull. 2001, 49 (8), 1027-1029.
30. Griffith, O. H.; Waggoner, A. S. Acc. Chem. Res. 1969, 2, 17-24.
31. Keith, A. D.; Snipes, W.; Mehlhorn, R. J.; Gunter, T. Biophys. J. 1977, 19, 205-218.
32. Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC Press: Boca Raton, 1995; p 7-1.
33. Lipinski, Ch. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Del. Rev. 2001, 46, 3-26.