Abstract
A series of new (thio)semicarbazones containing adamantane and 3,7-dimethyloctyl fragments was synthesized. The configuration of imine bond was proposed based on the characteristic signals of 1Н and 13С NMR spectra simulated by quantum-chemical calculations.
REFERENCES
Spilovska, K., Zemek, F., Korabecny, J., Nepovimova, E., Soukup, O., Windisch, M., and Kuca, K., Curr. Med. Chem., 2016, vol. 23, p. 3245. https://doi.org/10.2174/0929867323666160525114026
Wanka, L., Iqbal, K., and Schreiner, P.R., Chem. Rev., 2013, vol. 113, p. 3516. https://doi.org/10.1021/cr100264t
Siwek, A., Sta̧czek, P., and Stefańska, J., Eur. J. Med. Chem., 2011, vol. 46, p. 5717. https://doi.org/10.1016/j.ejmech.2011.09.034
Azam, F., Alkskas, I.A., Khokra, S.L., and Prakash, O., Eur. J. Med. Chem., 2009, vol. 44, p. 203. https://doi.org/10.1016/j.ejmech.2008.02.007
Abdul Manaf, A.M., Momin Khan, M.K., Khair Zaman, K.Z., Mahboob Ali, M.A., Faima Alam, F.A., Khalid Mohammed Khan, and Basharat Ali, K.M.K., J. Chem. Soc. Pakistan, 2021, vol. 43, p. 475. https://doi.org/10.52568/000592/JCSP/43.04.2021
Suslov, E.V., Mozhaytsev, E.S., Korchagina, D.V., Bormotov, N.I., Yarovaya, O.I., Volcho, K.P., Serova, O.A., Agafonov, A.P., Maksyutov, R.A., Shishkina, L.N., and Salakhutdinov, N.F., RSC Med. Chem., 2020, vol. 11, p. 1185. https://doi.org/10.1039/d0md00108b
Munkuev, A.A., Mozhaitsev, E.S., Chepanova, A.A., Suslov, E.V., Korchagina, D.V., Zakharova, O.D., Ilina, E.S., Dyrkheeva, N.S., Zakharenko, A.L., Reynisson, J., Volcho, K.P., Salakhutdinov, N.F., and Lavrik, O.I., Molecules, 2021, vol. 26, p. 1. https://doi.org/10.3390/molecules26113128
Palanimuthu, D., Wu, Z., Jansson, P.J., Braidy, N., Bernhardt, P.V., Richardson, D.R., and Kalinowski, D.S., Dalton Trans., 2018, vol. 47, p. 7190. https://doi.org/10.1039/c8dt01099d
He, Z.Y., Huang, C.F., and Tian, S.K., Org. Lett., 2017, vol. 19, p. 4850. https://doi.org/10.1021/acs.orglett.7b02312
Kreutzberger, A., Schröders, H.-H., and Stratmann, J., Arch. Pharm., 1984, vol. 317, p. 767. https://doi.org/10.1002/ardp.19843170907
Al-Abdullah, E.S., Al-Tuwaijri, H.M., Hassan, H.M., Al-Alshaikh, M.A., Habib, E.E., and El-Emam, A.A., Molecules, 2015, vol. 20, p. 8125. https://doi.org/10.3390/molecules20058125
Jakusová, K., Gáplovský, M., Donovalová, J., Cigáň, M., Stankovičová, H., Sokolík, R., Gašpar, J., and Gáplovský, A., Chem. Pap., 2013, vol. 67, p. 117. https://doi.org/10.2478/s11696-012-0248-x
Pracht, P., Bohle, F., and Grimme, S., Phys. Chem. Chem. Phys., 2020, vol. 22, p. 7169. https://doi.org/10.1039/c9cp06869d
Bannwarth, C., Ehlert, S., and Grimme, S., J. Chem. Theory Comput., 2019, vol. 15, p. 1652. https://doi.org/10.1021/acs.jctc.8b01176
Grimme, S., J. Chem. Theory Comput., 2019, vol. 15, p. 2847. https://doi.org/10.1021/acs.jctc.9b00143
Bannwarth, C., Caldeweyher, E., Ehlert, S., Hansen, A., Pracht, P., Seibert, J., Spicher, S., and Grimme, S., WIREs Comput. Mol. Sci., 2021, vol. 11, p. 1. https://doi.org/10.1002/wcms.1493
Neese, F., WIREs Comput. Mol. Sci., 2012, vol. 2, p. 73. https://doi.org/10.1002/wcms.81
Neese, F., WIREs Comput. Mol. Sci., 2022, vol. 12, p. 1. https://doi.org/10.1002/wcms.1606
Vosko, S.H., Wilk, L., and Nusair, M., Can. J. Phys., 1980, vol. 58, p. 1200. https://doi.org/10.1139/p80-159
Becke, A.D., J. Chem. Phys., 1992, vol. 96, p. 2155. https://doi.org/10.1063/1.462066
Stephens, P.J., Devlin, F.J., Chabalowski, C.F., and Frisch, M.J., J. Phys. Chem., 1994, vol. 98, p. 11623. https://doi.org/10.1021/j100096a001
Lee, C., Yang, W., and Parr, R.G., Phys. Rev. (B), 1988, vol. 37, p. 785. https://doi.org/10.1103/PhysRevB.37.785
Francl, M.M., Pietro, W.J., Hehre, W.J., Binkley, J.S., Gordon, M.S., DeFrees, D.J., and Pople, J.A., J. Chem. Phys., 1982, vol. 77, p. 3654. https://doi.org/10.1063/1.444267
Hehre, W.J., Ditchfield, R., and Pople, J.A., J. Chem. Phys., 1972, vol. 56, p. 2257. https://doi.org/10.1063/1.1677527
Weigend, F., Phys. Chem. Chem. Phys., 2006, vol. 8, p. 1057. https://doi.org/10.1039/b515623h
Grimme, S., Antony, J., Ehrlich, S., and Krieg, H., J. Chem. Phys., 2010, vol. 132, p. 154104. https://doi.org/10.1063/1.3382344
Grimme, S., Ehrlich, S., and Goerigk, L., J. Comput. Chem., 2011, vol. 32, p. 1456. https://doi.org/10.1002/jcc.21759
Del Campo, J.M., Gázquez, J.L., Trickey, S.B., and Vela, A., J. Chem. Phys., 2012, vol. 136, article 104108. https://doi.org/10.1063/1.3691197
Krishnan, R., Binkley, J.S., Seeger, R., and Pople, J.A., J. Chem. Phys., 1980, vol. 72, p. 650. https://doi.org/10.1063/1.438955
Clark, T., Chandrasekhar, J., Spitznagel, G.W., and Schleyer, P.V.R., J. Comput. Chem., 1983, vol. 4, p. 294. https://doi.org/10.1002/jcc.540040303
McLean, A.D. and Chandler, G.S., J. Chem. Phys., 1980, vol. 72, p. 5639. https://doi.org/10.1063/1.438980
Frisch, M.J., Pople, J.A., and Binkley, J.S., J. Chem. Phys., 1984, vol. 80, p. 3265. https://doi.org/10.1063/1.447079
Marenich, A.V., Cramer, C.J., and Truhlar, D.G., J. Phys. Chem. (B), 2009, vol. 113, p. 6378. https://doi.org/10.1021/jp810292n
Lodewyk, M.W., Siebert, M.R., and Tantillo, D.J., Chem. Rev., 2012, vol. 112, p. 1839. https://doi.org/10.1021/cr200106v
Burmistrov, V.V., Pershin, V.V., and Burov, G.M., Izv. VolGTU, 2012, vol. 5, p. 62.
Claremon, D.A., Singh, S.B., Tice, C.M., Ye, Y., Zhuang, L., Ye, Y., Singh, S.B., and Tice, C.M., Patent US WO 2009131669A2, 2009.
Burmistrov, V.V., Butov, G.M., and Pitushkin, D.A., Russ. J. Org. Chem., 2015, vol. 51, p. 1795. https://doi.org/10.1134/S1070428015120246
Pitushkin, D.A., Burmistrov, V.V., and Butov, G.M., Russ. J. Org. Chem., 2018, vol. 54, p. 1475. https://doi.org/10.1134/S1070428018100068
Odinokov, V.N., Ishmuratov, G.Y., Kharisov, R.Y., Lomakina, S.I., and Tolstikov, G.A., Bull. Acad. Sci. USSR Div. Chem. Sci., 1989, vol. 38, p. 1768. https://doi.org/10.1007/BF00956974
ACKNOWLEDGMENTS
The authors thank the Information and Computing Center of the Novosibirsk State University for the provided computing resources, and also express gratitude to the Chemical Research Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences for carrying out spectral and analytical measurements.
Funding
The work was financially supported by the Russian Science Foundation (grant no. 22-73-00340).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Additional information
To the 120th anniversary of B.A. Arbuzov
Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary information
Rights and permissions
About this article
Cite this article
Mozhaitsev, E.S., Marakulin, A.V., Suslov, E.V. et al. Synthesis of (Thio)semicarbazones Combining Adamantane and 3,7-Dimethyloctyl Fragments. Russ J Gen Chem 93 (Suppl 2), S450–S455 (2023). https://doi.org/10.1134/S1070363223150057
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363223150057