A chemonuclear method of synthesis is proposed for obtaining difficultly available phenyl-substituted derivatives of quinoline labeled with tritium. The ion-molecule reaction of free phenyl cations, generated on β-decay of tritium, with the nucleophilic centers of heterocyclic compounds is the basis of the synthesis. The onium derivatives synthesized possess significant inhibitory antimicrobial activity and are promising for a detailed study of the reaction mechanisms and metabolic processes using radioactive indicators.
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References
A. F. Pozharskii, A. T. Soldatenkov, and A. R. Katritzky, Heterocycles in Life and Society, Wiley, New York (1997).
J. A. Joule and K. Mills, Heterocyclic Chemistry, 4th Edition, Blackwell Science, (2000).
Chemistry of Organic Fluorine Compounds, II ACS Monograph 187, Washington DC (1995).
G. E. Pilyugin and B. M. Gutsulyak, Usp. Khim., 32, 167 (1963).
I. I. Sidorchuk, R. F. Stadniichuk, E. N. Tishchenko, and L. T. Bordyakovskaya, Khim.-Farm. Zh., 12, 78 (1978).
W. A. Cox, Appl. Microbiol., 13, 956 (1965).
B. K. Sinha, R. M. Philen, R. Sato, and R. L. Cysyk, J. Med. Chem., 20, 1528 (1977).
J. W. Bunting, K. R. Laderoute, and D. J. Norris, Can. J. Biochem., 58, 49 (1980).
S. M. Taylor, C. Stubley-Beedman, and J. G. P. Stell, Biochem. J., 220, 67 (1984).
C. Beedham, S. E. Bruce, D. I. Crithley, Y. Al-Tayib, and D. J. Rance, Eur. J. Drug Metab. Pharmacokinet., 12, 307 (1987).
G. A. Atwell, B. C. Baguley, and W. A. Denny, J. Med. Chem., 32, 396 (1989).
S. A. Rotenberg, S. Smiley, M. Ueffing, R. S. Krauss, L. B. Chen, and B. Weinstein, Cancer Res., 50, 677 (1990).
D. J. P. Critchley, D. J. Rance, and C. Beedham, Biophys. Res. Commun., 185, 54 (1992).
J. Stojan, V. Marcelb, and D. Fournierb, Chem.-Biol. Interactions, 119–120, 147 (1999).
M. Malik-Hal, R. Ganellin, D. Galanakis, and D. H. Jenkinson, Brit. J. Pharmacol., 129, 1431 (2000).
C. R. Joaquin, D. Galanakis, A. Piergentili, K. Bhandari, C. R. Ganellin, P. M. Dunn, and D. H. Jenkinson, J. Med. Chem., 43, 420 (2000).
C. Pina-Vaz, F. Sansonetty, A. G. Rodrigues, S. Costa-Oliveira, C. Tavares, and J. Martinez-de-Oliveira, Clin. Microbiol. Infection, 7, 609 (2001).
S. Jayaraman, Y. Song, V. L. Shankar, and A. S. Verkman, J. Clin. Invest., 107, 317 (2001).
K. A. Marr, M. Koudadoust, M. Black, and S. A. Balajee, Clin. Diagnostic Lab. Immunol., 8, 1240 (2001).
O. Kogi, H.-B. Kim, and N. Kitamura, Analyst, 127, 967 (2002).
P. K. Mukherjee, J. Chandra, D. M. Kuhn, and M. A. Ghannoum, Infection Immunity, 71, 4333 (2003).
T. N. Bennett, M. Paguio, B. Gligorijevic, C. Seudieu, A. D. Kosar, E. Davidson, and P. D. Roepe, Antimicrobial Agents Chemotherapy, 1807 (2004).
R. M. Abd El-Aala, and M. Younis, Bioorg. Chem., 32, 193 (2004).
M. Otarigi, Drug Metab. Pharmacokinet., 20, 309 (2005).
U.-C. Hipler, P. Elsner, and J. W. Fluhr, Curr. Probl. Dermatol., 33, 165 (2006).
C.-H. Lee, H. J. Kim, J.-H. Lee, H.-J. Cho, J. Kim, K. C. Chung, and S. Jung, J. Biol. Chem., 281, 3463 (2006).
M. Saljoughian, Synthesis, 1781 (2002).
G. V. Sidorov and N. F. Myasoedov, Usp. Khim., 13, 398 (1999).
V. P. Shevchenko, I. Yu. Nagaev, and N. F. Myasoedov, Lipophilic Compounds Labeled with Tritium [in Russian], Nauka, Moscow (2003).
K. H. Pausacker, Austr. J. Chem., 11, 200 (1958).
V. I. Ivanskii, Chemistry of Heterocyclic Compounds [in Russian], Vyssh. Shkola, Moscow (1978), p. 459.
C. Mortelmans and G. Van Binst, Tetrahedron, 34, 363 (1978).
T. L. Gilchrist, Heterocyclic Chemistry, 3rd Edit. Longmans, Harlow (1997), 414 pp.
A. R. Katritzky and A. F. Pozharski, Handbook of Heterocyclic Chemistry, Pergamon (2000).
G. T. Pilyugin and Z. Ya. Krainer, Dokl. Akad. Nauk, 81, 609 (1951).
V. D. Nefedov, E. N. Sinotova, M. V. Korsakov, and E. G. Alekseev, Radiokhimiya, 15, 635 (1973).
N. E. Shchepina, V. V. Avrorin, G. A. Badun, V. M. Fedoseev, S. E. Ukhanov, and S. B. Lewis, Radiokhimiya, 49, 551 (2007).
A. F. Pozharskii, Theoretical Basis of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).
V. D. Nefedov, M. A. Toropova, V. V. Avrorin, D. S. Gembitskii, S. B. Lewis, and B. Mettson, Radiokhimiya, 41, 523 (1999).
M. Charton, J. Am. Chem. Soc., 86, 2033 (1964).
M. Charton, J. Org. Chem., 30, 3341 (1965).
R. F. Stadniichuk, G. T. Pilugin, and O. E. Petrenko, Zh. Obshch. Khim., 40, 1834 (1970).
B. I. Ardashev and V. I. Minkin, Zh. Obshch. Khim., 29, 200 (1959).
M. I. Rogovik, I. N. Chernyak, Yu. S. Rozum, and G. T. Pilyugin, Zh. Obshch. Khim., 34, 3320 (1964).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1008-1014, July, 2009.
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Shchepina, N.E., Avrorin, V.V., Badun, G.A. et al. Preparation of N-phenyl-substituted quinolinium derivatives labeled with tritium by chemonuclear synthesis. Chem Heterocycl Comp 45, 796–801 (2009). https://doi.org/10.1007/s10593-009-0359-7
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DOI: https://doi.org/10.1007/s10593-009-0359-7