New hybrid compounds of abietic acid with 2-thione-, 2-alkylthio-, and 2-alkylamino-1,3,4-oxadiazole fragments at various distances from the diterpene skeleton were synthesized in situ via cyclization in acidic medium of intermediate dithiocarbamates or cyclodesulfurization of intermediate acylthiosemicarbazides through the action of Hg(OAc)2.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
S. Choudhary, P. K. Singh, H. Verma, H. Singh, and O. Silakari, Eur. J. Med. Chem., 151, 62 (2018).
V. A. Pentegova, Zh. V. Dubovenko, V. A. Raldugin, and E. N. Shmidt, Terpenoids of Coniferous Plants [in Russian], Nauka, Novosibirsk, 1987.
G. A. Tolstikov, T. G. Tolstikova, E. E. Shul′ts, S. E. Tolstikov, and M. V. Khvostov, Resinous Acids of Conifers of Russia. Chemistry and Pharmacology [in Russian], Akademicheskoe Izd. Geo, Novosibirsk, 2011; X. Liu, W. Chen, Q. Liu, and J. Dai, OncoTargets Ther., 12, 4825 (2019).
C. Faustino, I. Neto, P. Fonte, and A. Macedo, Curr. Pharm. Des., 24, 4362 (2019).
T. Glomb, K. Szymankiewicz, and P. Swiatek, Molecules, 23, 3361 (2018).
J. Bostrom, A. Hogner, A. Llinas, E. Wellner, and A. T. Plowright, J. Med. Chem., 55, 1817 (2012).
S. M. Abou-Seri, Eur. J. Med. Chem., 45, 4113 (2010); J. Raval, T. Akhaja, D. Jaspara, K. Myangar, and N. Patel, J. Saudi Chem. Soc., 18, 101 (2014); S. Nayak, S. L. Gaonkar, E. A. Musad, and A. M. Al Dawsar, J. Saudi Chem. Soc., 25, 101284 (2021).
I. I. Bardyshev, Zh. Org. Khim., 35, 48 (1999).
S. A. Popov, M. D. Semenova, D. S. Baev, T. S. Frolova, E. E. Shults, C. Wang, and M. Turks, Steroids, 153, 108524 (2020).
D. A. Charistos, G. V. Vagenas, L. C. Tzavellas, C. A. Tsoleridis, and N. A. Rodios, J. Heterocycl. Chem., 31, 1593 (1994).
M. D. Semenova, S. A. Popov, T. S. Golubeva, D. S. Baev, E. E. Shults, and M. Turks, Chemistry Select, 6, 6472 (2021).
W. G. Duan, X. R. Li, Q. J. Mo, J. X. Huang, B. Cen, X. T. Xu, and F. H. Lei, Holzforschung, 65, 191 (2011).
Q.-J. Mo, W.-G. Duan, X.-R. Li, D.-P. Huang, and Z.-J. Luo, Chin. J. Org. Chem., 31, 1114 (2011).
Acknowledgment
The work was performed under State Task 1021051503128-9-1.4.1. We thank Khimiya Common Use Center, SB, RAS, for performing the spectral and analytical measurements.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2022, pp. 252–257.
Rights and permissions
About this article
Cite this article
Shpatov, A.V., Zakharova, S.S. & Popov, S.A. Synthesis of New Hybrids of Abietic Acid and 1,3,4-Oxadiazoles. Chem Nat Compd 58, 290–296 (2022). https://doi.org/10.1007/s10600-022-03662-5
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-022-03662-5