In this study the
compatible chemical and biological investigations of several N-phenylquinolinium
derivatives have been carried out in order to find the most perspective
quinolinium structures for the nuclear-chemical synthesis of tritium labeled
biomarkers.
References
[1]
Pozharskii, A.F., Soldatenkov, A.T. and Katritzky, A.R. (1997) Heterocycles in Life and Society. John Wiley & Sons Ltd., New York.
[2]
Carey, J.S., Laffan, D., Thomson, C. and Williams, M.T. (2006) Analysis of the Reactions Used for the Preparation of Drug Candidate Molecules. Organic and Biomolecular Chemistry, 4, 2337-2347. http://dx.doi.org/10.1039/b602413k
[3]
Zhao, T. and Sun, G. (2008) Hydrophobicity and Antimicrobial Activities of Quaternary Pyridinium Salts. Journal of Applied Microbiology, 104, 824-830. http://dx.doi.org/10.1111/j.1365-2672.2007.03616.x
[4]
Laufer, R., Bathori, M., Csermery, T., Petroiani, G., Kuca, K., Toth, N. and Kalasz, H. (2007) LC Determination of Hydrophilicity Parameter of Some Pyridinium Aldoximes. Journal of Liquid Chromatography and Related Technologies, 30, 2337-2344. http://dx.doi.org/10.1080/10826070701451738
[5]
Kumar, V. and Malhotra, S.V. (2010) Ionic Liquids as Pharmaceutical Salts: A Historical Perspective. ACS Symposium Series, 1038, 1-12.
[6]
Docherty, K. and Kulpa, C.F. (2005) Toxicity and Antimicrobial Activity of Imidazolium and Pyridinium Ionic Liquids. Green Chemistry, 7, 185-189. http://dx.doi.org/10.1039/b419172b
[7]
Zhao, T. and Sun, G. (2006) Synthesis and Characterization of Antimicrobial Cationic Surfactants: Aminopyridinium Salts. Journal of Surfactants and Detergents, 9, 325-330. http://dx.doi.org/10.1007/s11743-006-5010-3
[8]
Musilek, K., Kusa, K., Jun, D., Dohnal, V. and Dolezal, M. (2005) Synthesis of a Novel Series of Bispyridinium Compounds Bearing a Xylene Linker and Evaluation of Their Reactivation Activity Against Chlorpyyrifos-Inhibited Acetylcholinnesterase. Journal of Enzyme Inhibition and Medicinal Chemistry, 20, 409-415. http://dx.doi.org/10.1080/14756360500179762
[9]
Gutsulyak, B.M. (1972) Biological Activity of Quinolinium Salts. Russian Chemical Reviews, 41, 187-202. http://dx.doi.org/10.1070/RC1972v041n02ABEH002038
Voznyak, V.I., Savitskaya, L.G. and Neporadnyi, D.D. (1984) Antimicrobial Activity of Quaternary 4-(P-Dimethylaminostyryl)Quinolinium Salts. Pharmaceutical Chemistry Journal, 18, 561-563.
[12]
Cox, O., Jackson, H., Vargas, A., Báez, A., Colón, J.I., González, B.C. and de León, M. (1982) Synthesis and Biological Activity of Benzothiazoloand Benzoxazolo[3, 2-a]Quinolinium Salts. Journal of Medicinal Chemistry, 25, 13781381. http://dx.doi.org/10.1021/jm00353a020
[13]
Hernández, H.J. (1982) Synthesis and Biological Activity of Some Benzoheterazolo (3, 2-a) Quinolinium Salts. Universidad de Puerto Rico, 208.
[14]
Joaquin, C.R., Galanakis, D., Piergentili, A., Bhandari, K., Ganellin, C.R., Dunn, P.M. and Jenkinson, D.H. (2000) Synthesis, Molecular Modeling, and Pharmacological Testing of Bis-Quinolinium Cyclophanes: Potent, Non-Peptidic Blockers of the Apamin-Sensitive Ca2+-Activated K+ Channel. Journal of Medicinal Chemistry, 43, 420-431. http://dx.doi.org/10.1021/jm9902537
[15]
Campos, J.M., Nú-ez, M.C., Sánchez, R.M., Gómez-Vidal, J.A., Rodríguez-González, A., Bá-ez, M., Gallo, M.A., Lacal, J.C. and Espinosa, A. (2002) Quantitative Structure-Activity Relationships for a Series of Symmetrical Bisquaternary Anticancer Compounds. Bioorganic & Medicinal Chemistry, 10, 2215-2231. http://dx.doi.org/10.1016/S0968-0896(02)00054-8
[16]
Barchéchath, S.D., Tawatao, R.I., Corr, M., Carson, D.A. and Cottam, H.B. (2005) Quinolinium Salt as a Potent Inhibitor of Lymphocyte Apoptosis. Bioorganic & Medicinal Chemistry Letters, 15, 1785-1788. http://dx.doi.org/10.1016/j.bmcl.2005.02.047
[17]
Srivani, P. and Sastry, G.N. (2009) Potential Choline Kinase Inhibitors: A Molecular Modeling Study of Bis-Quinolinium Compounds. Journal of Molecular Graphics & Modelling, 27, 676-688. http://dx.doi.org/10.1016/j.jmgm.2008.10.010
[18]
Zayas, B. and Cox, O. (2012) Method for Producing Benzazoloquinolium (BQs) Salts, Using the Composition as Cellular Markers, and Using the Biological Activity of the Composition. US Patent No. 20120129882.
[19]
Vélez, C., Cox, O., Rosado-Berrios, C.A., Molina, D., Arroyo, L., Carro, S., Filikov, A., Kumar, V., Malhotra, S.V., Cordero, M. and Zayas, B. (2013) Novel Nitrobenzazolo [3, 2-a] Quinolinium Salts Induce Cell Death through a Mechanism Involving DNA Damage, Cell Cycle Changes, and Mitochondrial Permeabilization. Open Journal of Apoptosis, 2, 13-22. http://dx.doi.org/10.4236/ojapo.2013.22002
[20]
Bringmanna, G., Thomale, K., Bischof, S., Schneider, C., Schultheis, M., Schwarz, T., Mollb, H. and Schurigtb, U. (2013) A Novel Leishmania major Amastigote Assay in 96-Well Format for Rapid Drug Screening and Its Use for Discovery and Evaluation of a New Class of Leishmanicidal Quinolinium Salts. Antimicrobial Agents and Chemotherapy, 57, 3003-3011. http://dx.doi.org/10.1128/AAC.02201-12
[21]
Pausacker, K.H. (1958) Arylation of Aromatic Compounds. VI. Benzoyl Peroxide with Pyridine and Quinoline. Australian Journal of Chemistry, 11, 200-210. http://dx.doi.org/10.1071/CH9580200
[22]
Brody, F. and Ruby, P.R. (1960) Pyridine and Its Derivatives. Part I, In Klingsberg, Ed., Interscience Publishers, Inc., New York.
[23]
Shchepina, N.E., Avrorin, V.V., Badun, G.A., Lewis, S.B., Fedoseev, V.M. and Ukhanov, S.E. (2009) The Reaction of Direct Phenylation by Nucleogenic Cations as a Method of Synthesis of Unknown or Complicated Tritium Labeled Compounds. Moscow University Chemistry Bulletin, 64, 244-248. http://dx.doi.org/10.3103/S0027131409050034
[24]
Shchepina, N.E., Avrorin, V.V., Badun, G.A., Alexandrova, G.A., Ukhanov, S.E., Fedoseev, V.M. and Boiko, I.I. (2009) Preparation of N-Phenyl-Substituted Quinolinium Derivatives Labeled with Tritium by Chemonuclear Synthesis. Chemistry of Heterocyclic Compounds, 45, 796-801. http://dx.doi.org/10.1007/s10593-009-0359-7
[25]
Shchepina, N.E., Avrorin, V.V., Badun, G.A., Fedoseev, V.M. and Lewis, S.B. (2010) New Method for the Synthesis of Difficultly Available Sterically Hindered Tritium-Labeled Pyridinium Derivatives. Chemistry of Heterocyclic Compounds, 46, 547-552. http://dx.doi.org/10.1007/s10593-010-0544-8
[26]
Shchepina, N.E., Avrorin, V.V., Badun, G.A., Bumagin, N.A., Lewis, S.B. and Shurov S.N. (2012) Pathways of Ionmolecular Interactions of Nucleogenic Phenyl Cations with the Nucleophilic Centers of Picolines. Organic and Medicinal Chemistry Letters, 2, 14. http://dx.doi.org/10.1186/2191-2858-2-14
[27]
Shchepina, N.E., Avrorin, V.V., Alexandrova, G.A., Badun, G.A., Boiko, I.I. and Shurov, S.N. (2013) Investigation of the Phenylation of Methyl-Quinolines Using Tritium-Labeled Nucleogenic Phenyl Cations. Chemistry of Heterocyclic Compounds, 49, 428-434. http://dx.doi.org/10.1007/s10593-013-1264-7
[28]
Pilyugin, G.T. and Gutsulyak, B.M. (1963) Advances in the Preparation, Investigation, and Use of Quinolinium Compounds. Russian Chemical Reviews, 32, 167-188. http://dx.doi.org/10.1070/RC1963v032n04ABEH001327
[29]
Pilyugin, G.T. and Krainer, Z.Y. (1951) Phenylsubstituted Quinocyanines. Doklady Akademii Nauk, 8, 609-612.
[30]
Chernyuk, I.N., Pilyugin, G.T. and Zlochevskaya, A.V. (1970) Studies in the Field of Synthetic Dyes. Chemistry of Heterocyclic Compounds, 4, 236-237. http://dx.doi.org/10.1007/BF00601137
[31]
Pilyugin, G.T. and Gutsulyak, B.M. (1959) Studies of Synthetic Dyes: Synthesis of n-Phenyllepidine Perchlorate and Some of Its Transformation. XIV. Zhurnal Obshchei Khimii, 29, 3076-3079.
[32]
Pilyugin, G.T. and Opanasenko, E.P. (1952) Synthesis of β-Naphtoquinaldine Iodinephenilate and Its Transformations. Ukrainskii Khimicheskii Zhurnal (Russian Edition), 18, 625-630.
[33]
Shchepina, N.E., Boiko, I.I. and Aleksandrova, G.A. (2011) Synthesis and Antimicrobial Activity of Quaternary N-Aryl-5, 6-benzoquinaldinium Derivatives. Pharmaceutical Chemistry Journal, 45, 159-161. http://dx.doi.org/10.1007/s11094-011-0583-1
[34]
Pilyugin, G.T. and Opanasenko, E.P. (1957) Cyandyes. VII. Cyclization of Secondary Aromatic Amines with Vinyl Ethers and Arylquinaldinium Derivatives Formation. Zhurnal Obshchei Khimii, 27, 1015-1018.
[35]
Pilyugin, G.T., Gorichok, Ya.O., Gutsulyak, B.M. and Gorichok, S.I. (1965) Researches on Synthetic Dyes. Chemistry of Heterocyclic Compounds, 1, 603-608. http://dx.doi.org/10.1007/BF00472701
[36]
Shchepina, N.E., Avrorin, V.V., Badun, G.A., Lewis, S.B. and Ukhanov, S.E. (2012) Preparation of Fused N-Phenylsubstituted Pyridinium Derivatives by Direct Phenylation with Nucleogenic Phenyl Cations. Chemistry of Heterocyclic Compounds, 48, 301-308. http://dx.doi.org/10.1007/s10593-012-0990-6
[37]
Pershin, G.N. (1971) Methods of Experimental Chemotherapy. Medgiz, Moscow.
