A series of carbamate-functionalized spiro compounds were synthesized by [3+2]-cycloaddition and condensation reactions based on methyl {4(3)-[2-(2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetyl]phenyl}carbamates. The antimicrobial activity with respect to E. coli, S. aureus 209, and Micrococcus and antifungal activity with respect to Microsporum canis, Trichophyton rubrum, and Candida albicans were investigated. The most active of the synthesized compounds were spiro compounds with isoxazoline and pyrazole fragments.
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References
A. V. Velikorodov and L. T. Sukhenko, Khim.-farm. Zh., 35(4), 24 – 25 (2001).
A. V. Velikorodov and L. T. Sukhenko, Khim.-farm. Zh., 37(1), 24 – 26 (2003).
F. Adelowo-Imeokparia, I. A. O. Ojo, and O. S. Amuda, World J. Agric. Sci., 4(1), 48 – 52 (2008).
F. Adelowo-Imeokparia, O. O. P. Faboya, and I. A. O. Ojo, Int. J. Chem., 15(2), 101 – 111 (2005).
A. V. Velikorodov, V. B. Kovalev, O. V. Degtyarev, and O. L. Titova, Khim.-farm. Zh., 44(10), 15 – 18 (2010).
A. V. Velikorodov, N. M. Imasheva, A. K. Kuanchalieva, and O. Yu. Poddubnyi, Zh. Org. Khim., 46(7), 975 – 979 (2010).
A. B. Serov, Candidate Dissertation in Chemical Sciences, Nizhnii Novgorod (2007).
A. B. Serov, V. G. Kartsev, Yu. A. Alexandrov, and F. M. Dolgushin, Russ. Chem. Bull., 54, 2432 – 2436 (2005).
S. Manikandan, M. M. Ashraf, and R. Raghunathan, Synth. Commun., 31, 3593 – 3601 (2001).
Rathna Durga R. S. Manian, J. Jayashankaran, S. S. Kumar, and R. Raghunathan, Tetrahedron Lett., 47, 829 – 832 (2006).
A. V. Velikorodov, O. Yu. Poddubnyi, O. O. Krivosheev, and O. L. Titova, Zh. Org. Khim., 47(3), 409 – 411 (2011).
A. L. Tokes, A. Szollosy, and A. Levai, Acta Chim. Hung., 112, 335 – 338 (1983).
A. Mustafa and M. K. Hilmy, J. Chem. Soc., 3254 – 3257 (1951).
G. Toth, A. Levai, A. Szollosy, and H. Duddeck, Tetrahedron, 49, 863 – 880 (1993).
A. Levai, Khim. Geterotsikl. Soedin., 6, 579 – 581 (1997).
F. Z. Makaev, Chemistry of Synthetic Indole Systems [in Russian], IBS Press (2004), Vol. 3, pp. 157 – 187.
A. V. Velikorodov, O. Yu. Poddubnyi, A. K. Kuanchalieva, and O. O. Krivosheev, Zh. Org. Khim., 46(12), 1816 – 1819 (2010).
D. N. Dhar, The Chemistry of Chalcones and Related Compounds, Wiley-Interscience, New York (1981).
A. S. Labinskaya, Microbiology with Microbiological Research Techniques [in Russian], Meditsina, Moscow (1972).
A. I. Korotyaev and S. A. Babichev, Medical Microbiology, Immunology, and Virusology [in Russian], Spetsliteratura, St. Petersburg (1998).
F. Espinel-Ingroff, K. Boyle, and D. J. Sheehan, Mycopathologia, 150, 101 – 115 (2001).
J. H. Rex, M. A. Pfaller, J. N. Galgiani, et al., Clin. Infect. Dis., 24(2), 248 – 249 (1997).
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Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 46, No. 12, pp. 19–23, December, 2012.
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Velikorodov, A.V., Ionova, V.A., Degtyarev, O.V. et al. Synthesis and Antimicrobial and Antifungal Activity of Carbamate-Functionized Spiro Compounds. Pharm Chem J 46, 715–719 (2013). https://doi.org/10.1007/s11094-013-0876-7
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DOI: https://doi.org/10.1007/s11094-013-0876-7