Статья
2021
Some Features of Phosphorylation and Benzoylation of Pyridoxal Imidazolidines
L. K. Kibardina, A. V. Trifonov, A. B. Dobrynin, M. A. Pudovik, A. R. Burilov
Российский журнал общей химии
https://doi.org/10.1134/S1070363221090097
Abstract / Full Text
The reactions of pyridoxal imidazolidines with diphenylchlorophosphine oxide, depending on the substituents nature in the imidazolidine ring, resulted in the formation of new salt-like tricyclic structures or a bisalt structure based on N,N′-dibenzylethylenediamine and diphenylphosphinic acid. The benzoylation of pyridoxal imidazolidines also led to decomposition of the imidazolidine fragment with the formation of dibenzoylated N,N′-dimethylethylenediamine.
Author information
- Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088, Kazan, RussiaL. K. Kibardina, A. V. Trifonov, A. B. Dobrynin, M. A. Pudovik & A. R. Burilov
References
- Speck, U., Patent US 5288716, 1994. USA.
- Müller, I.B., Wu, F., Bergmann, B., Knöckel, J., Walter, R.D., Gehring, H., and Wrenger, C., PLoS One, 2009, vol. 4, p. 4406. https://doi.org/10.1371/journal.pone.0004406
- Brokamp, R., Bergmann, B., Müller, I.B., and Bienz, S., Bioorg. Med. Chem., 2014, vol. 22, p. 1832. https://doi.org/10.1016/j.bmc.2014.01.057
- Zhuravel, I.O., Kovalenko, S.M., Ivachtchenko, A.V., Balakin, K.V., and Kazmirchuk, V.V., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 5483. https://doi.org/10.1016/j.bmcl.2005.08.081
- Heidari, A., Noshiranzadeh, N., Haghi, F., and Bikas, R., Microb. Pathogenesis, 2017, vol. 112, p. 103. https://doi.org/10.1016/j.micpath.2017.09.043
- Pereira, M.B., Fontana, L.A., Siqueira, J.D., Auras, B.L., Da Silva, M.P., Neves, A., Gabriel, P., Terenzi, H., Iglesias, B.A., and Back, D.F., Inorg. Chim. Acta, 2018, vol. 469, p. 561. https://doi.org/10.1016/j.ica.2017.09.063
- Kesel, A.J., Bioorg. Med. Chem., 2003, vol. 11, p. 4599. https://doi.org/10.1016/S0968-0896(03)00500-5
- Garay, R.P., Nazaret, C., Diez, J., Etienne, A., Bourgain, R., and Braquet, P., Biochem. Pharmacol., 1984, vol. 33, p. 2013. https://doi.org/10.1016/0006-2952(84)90567-7
- Page, J., Page, K., and Cornett, G., US Patent EP 1951264, 2008.
- Bagrov, A.Y., Dmitrieva, R.I., Dorofeeva, N.A., Fedorova, O.V., Lopatin, D.A., Lakatta, E.G., and Droy-Lefaix, M.T., J. Hypertens., 2000, vol. 18. 209. https://doi.org/10.1097/00004872-200018020-00012
- Heyl, D., Luz, E., Harris, S.A., and Folkers, K., J. Am. Chem. Soc., 1951, vol. 73, p. 3430. https://doi.org/10.1021/ja01151a125
- Kibardina, L.K., Trifonov, A.V., Burilov, A.R., Pudovik, M.A., Dobrynin, A.B., and Pudovik, E.M., Russ. J. Org. Chem., 2015, vol. 51, p. 1510. https://doi.org/10.1134/S1070428015100280
- Kibardina, L.K., Chumakova, L.V., Gazizov, A.S., Burilov, A.R., and Pudovik, M.A., Synthesis, 2015, vol. 47, p. 721. https://doi.org/10.1055/s-0034-1378684
- Naskar, S., Butcher, R.J., and Chattopadhyay, S.K., Inorg. Chim. Acta, 2010, vol. 363, p. 404. https://doi.org/10.1016/j.ica.2009.11.007
- Sharif, Sh., Schagen, D., Toney, M.D., and Limbach, H.H., J. Am. Chem. Soc., 2007, vol. 129, p. 4440. https://doi.org/10.1021/ja066240h
- Kibardina, L.K., Trifonov, A.V., Dobrynin, A.B., Pudovik, M.A., and Burilov, A.R., Mendeleev Commun., 2018, vol. 28, p. 551. https://doi.org/10.1016/j.mencom.2018.09.035
- Nakagawa, K., Yoshimura, I., Sueda, N., and Fukawa, H., Agric. Biol. Chem., 1977, vol. 41, p. 1431. https://doi.org/10.1271/bbb1961.41.1431
- Hongping, B. and Houyuan, Z., China Patent CN101525330 (A), 2009.
- Kibardina, L.K., Bagautdinova, R.H., Dobrynin, A.B., Burilov, A.R., Pudovik, M.A., Trifonov, A.V., and Pudovik, E.M., Russ. J. Gen. Chem., 2016, vol. 86, p. 607. https://doi.org/10.1134/S1070363216030178
- Karlsson, S., Liljefors, T., and Sandström, J., Acta Chem. Scand. (B), 1977, vol. 31, p. 399. https://doi.org/10.3891/acta.chem.scand.31b-0399
- Bauer, L., J. Am. Chem. Soc., 1956, vol. 78, p. 1945. https://doi.org/10.1021/ja01590a049
- Sheldrick, G.M., SADABS. Bruker AXS Inc., Madison, USA, 1997.
- Altomare, A., Cascarano, G., Giacovazzo, C., and Viterbo, D., Acta Crystallogr. (A), 1991, vol. 47, p. 744. https://doi.org/10.1107/S0108767391006566
- Sheldrick, G.M., SHELX-97. Programs for Crystal Structure Analysis (Release 97-2). University of Göttingen, 1997, vol. 1, 2.
- Farrugia, L.J., J. Appl. Crystallogr., 1999, vol. 32, p. 837. https://doi.org/10.1107/S0021889899006020
- APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A), Bruker Advanced X-ray Solutions, Bruker AXS Inc., Madison, Wisconsin, USA, 2006.