STUDYING THE KINETICS OF LIQUID PHASE HYDRAZINOLYSIS BUTYL 2-(2R-9-OXOACRIDINE-10(9H)-YL)ACETATES
Synthesis, the study of chemical, physical and biological properties, as well as the practical value of the new derivatives of acridine-9(10H)–one is one of the promising directions in the chemistry of heterocyclic compounds. The study concerns the synthesis of hydrazides of 2-(2R-9-oxoacridine-10(9H)-yl)ethanoic acids, which due to their reactivity are widely used for the synthesis of various nitrogen-containing heterocyclic systems, such as: 1,3,4‑oxadiazole, 1,2,4-triazole and 1,3,4-thiadiazole. The substituted organic hydrazides of 2-(2R-9-oxoacridine-10(9H)-yl)ethanoic acids are widely used in organic and bioorganic chemistry. In this work, the kinetics of the liquid-phase hydrazinolysis of butyl 2-(2R-9-oxoacridine-10(9H)-yl)ethanoates was studied. At the beginning of the study, the thermodynamic characteristics of the reaction and the activation energy were theoretically calculated using GAMESS program. It was found that the activation energy for the formation of 2-(9-oxoacridine-10(9H)-yl)acetohydrazide is 60.47 kJ/mol, and for 2-(2-methyl-9-oxoacridine-10(9H)-yl)acetohydrazide it is 27.09 kJ/mol. Consequently, the reaction of hydrazine with butyl 2-(2-methyl-9-oxoacridine-10(9H)-yl)ethonoate occurs 2.2 times faster than butyl 2-(9-oxoacridine-10(9H)-yl)ethanoate. Subsequently, the kinetics of the reaction of liquid-phase hydrazinolysis was experimentally investigated by the consumption of hydrazine-hydrate in the reaction for the confirmation of theoretical calculations. In the temperature range of 298–343 K the activation energy of the process found from Arrhenius dependence is 15.78 and 7.24 kJ/mol. It is shown that the reaction has a second order of bimolecular substitution. There is proposed a mechanism of the process on the basis of kinetic data.
Full Text:PDF (Українська)
Svoboda, G. H., Poore, G. A., Simpson, P. J., Boder, G. B. (1966). Alkaloids of Acronychia Baueri Schott I. Isolation of the alkaloids and a study of the antitumor and other biological properties of acronycine. Journal of pharmaceutical sciences, 55(8), 758–768.
Shoji, A., Hasegawa, T., Kuwahara, M., Ozaki, H., Sawai, H. (2007). Chemico-enzymatic synthesis of a new fluorescent-labeled DNA by PCR with a thymidine nucleotide analogue bearing an acridone derivative. Bioorg. Med. Chem. Lett., 17(3), 776‒779. https://doi.org/10.1016/j.bmcl.2006.10.072
Sondhi, S. M., Singh, J., Rani, R., Gupta, P. P., Agrawal, S. K., Saxena, A. K. (2010). Synthesis, anti-inflammatory and anticancer activity evaluation of some novel acridine derivatives. Eur. J. Med. Chem., 45(2), 555‒563. https://doi.org/10.1016/j.ejmech.2009.10.042
Xu, L., Li, S., Liang, Z., Lin, H., Fu, R. (2017). Acridone suppresses the proliferation of human breast cancer cells in vitro via ATP-binding cassette subfamily G member 2. Oncology Letters, 15, 2651‒2654. https://doi.org/10.3892/ol.2017.7583
Mahajan, A. A., Rane, R. A., Amritkar, A. A., Naphade, S. S., Miniyar, P. B., Bangalore, P. K., Karpoormath, R. (2015). Synthesis of novel amides based on acridone scaffold with interesting antineoplastic activity. Anticancer. Agents Med. Chem., 15(5), 555‒564. http://www.ncbi.nlm.nih.gov/pubmed/25469511
Karpenko, Y. V., Omelyanchik, L. O. (2017). [Synthesis of heteryl derivatives of 2,5-disubstituted 1,3,4-okasadiazole]. Zh. Org. Farm. Khim., 15(4), 21‒32. (in Russian). https://doi.org/10.24959/ophcj.17.917
Campos, G. R. F.; Bittar, C.; Jardim, A. C. G.; Shimizu, J. F.; Batista, M. N.; Paganini, E. R.; Assis, L. R.; Bartlett, C.; Harris, M.; Bolzani, V. S.; Regasini, L. O.; Rahal, P. J. (2017). Hepatitis C virus in vitro replication is efficiently inhibited by acridone Fac4. J.Gen. Virol., 98(7), 1693‒1701. http://www.microbiologyresearch.org/content/journal/jgv/10.1099/jgv.0.000808
Omelʹyanchyk, L. A. (1991). [Sintez, svoystva i biologicheskaya aktivnost N- i S–zameshchennykh akridina, khinolina, piridina] (Unpublished habil. doctoral dissertation). Zaporizhzhia State Medical University, Zaporizhzhia, Ukraine (in Russian).
Kudryavtseva, T. N., Sysoev, P. I., Popkov, S. V., Nazarov, G. V., Klimova, L. G. (2015). Synthesis and antimicrobial activity of some acridone derivatives bearing 1,3,4-oxadiazole moiety. Russ. Chem. Bull, 64(6), 1341‒1344. https://doi.org/10.1007/s11172-015-1015-2
Gensicka-Kowalewska, M., Cholewiński, G., Dzierzbicka, K. (2017). Recent developments in the synthesis and biological activity of acridine/acridone analogues. RSC Adv., 7(26), 15776‒15804.
Kytaev, Yu. P., Buzykyn, B. I. (1974). [Hydrazony]. Moskow, USSR: Nauka (in Russian).
Majumdar, P., Pati, A., Patra, M., Beherat, R. K., Behera, A. K. (2014). Acid hydrazides, potent reagents for synthesis of Oxygen-, Nitrogen-, and/or Sulfur- containing heterocyclic rings. Chem. Rev. (Washington, DC, U. S.), 114(5), 2942–2977. https://doi.org/10.1021/cr300122t
Oliveira, C. S., Lira, B. F., Barbosa-Filho, J. M., Lorenzo, J. G. F., Athayde-Filho, P. F. (2012). Synthetic Approaches and Pharmacological Activity of 1,3,4-Oxadiazoles: A Review of the Literature from 2000‒2012. Molecules, 17(9), 10192‒10231. http://dx.doi.org/10.3390/molecules170910192
Fröhlichová, Z., Tomaščiková, J., Imrich, I., Kristian, P., Danihel, I., Böhm, S., Sabolová, D., Kožurková, M, Klika, K. D. (2009). Synthesis and Properties of Novel Biologically Interesting Polycyclic 1,3,4-Oxadiazoles Containing Acridine/Acridone Moieties. Heterocycles, 77(2), 1019‒1035. http://dx.doi.org/10.3987/COM-08-S(F)80
Barton, D., Olisa, U. D. (1985). [Total organic chemistry (Volume 8. Nitrogen-containing heterocycles)] Moskow, USSR: Khimiya (in Russian).
Bedlovičová, Z., Imrich, J., Kristian, P., Danihel, I., Böhm, S., Sabolová, D., Kožurková, M., Paulíková, H., Klika, K. D. (2010). Novel Carbohydrazide and Hydrazone Biomarkers Based on 9-Substituted Acridine and Anthracene Fluorogens. Heterocycles, 80(2), 1047‒1066. http://dx.doi.org/10.3987/COM-09-S(S)83
Euro-Asian Council for Standardization, Metrology and Certification. (1988). [Gosudarstvennyy standart SSSR gidrazin-gidrat tekhnicheskiy]. (GOST 19503-88). Moskow, USSR: Izdatelstvo standartov (in Russian).
Yatsymyrskyy, K. B. (1967). [Kineticheskie metody analiza]. Moskow, USSR: Khimiya (in Russian).
Arthur, E. L., Weissberger, J. C. (1971). Technique of organic chemistry. New York, Interscience.
Sysoev, P. I. (2015). [Sintez geterotsiklicheskikh soedineniy na osnove proizvodnykh akridonuksusnoy kisloty] (Unpublished habil. PhD dissertation). Kursk State University, Kursk, Russian (in Russian).
Marcus, D. H., Donald, E C., David, C. L., Vandermeersch, T., Zurek, E., Hutchison, G. R. (2012). Avogadro: An advanced semantic chemical editor, visualization, and analysis platform. J. Cheminf., 4, 1‒17. https://doi.org/10.1186/1758-2946-4-17
Gordon, M. S., Schmidt, M. W. (2005). Chapter 41 – Advances in electronic structure theory: GAMESS a decade later. Theory Appl. Comput. Chem.: First Forty Years, 1167–1189. https://doi.org/10.1016/B978-044451719-7/50084-6
Tirado-Rives, J., Jorgensen W. L. (2008). Performance of B3LYP Density Functional Methods for a Large Set of Organic Molecules. J. Chem. Theory Comput., 4(2), 297–306. http://dx.doi.org/10.1021/ct700248k
Bloino, J., Baiardi, A., Biczysko, M. (2016). Aiming at an accurate prediction of vibrational and electronic spectra for medium-to-large molecules: An overview. Int. J. Quantum Chem., 116(21), 1543–1574. http://dx.doi.org/10.1002/qua.25188
Caricato, M. (2012). Exploring Potential Energy Surfaces of Electronic Excited States in Solution with the EOM-CCSD-PCM Method. Journal of Chemical Theory and Computation, 8(12), 5081‒5091. http://dx.doi.org/10.1021/ct300382a
This work is licensed under a Creative Commons Attribution 4.0 International License.
Journal of Chemistry and Technologies
eISSN: 2663-2942 | pISSN: 2663-2934
Address of founder:email@example.com
The journal publishes scientific works on conditions: Creative Commons Attribution 4.0 International License
Founder: Oles Honchar Dnipro National University