The first nitrone-containing pentacyclic triterpenoid derivatives were synthesized from betulone and dihydrobetulone aldehydes and 3β-hydroxyaminolup-20(29)-en-28-al oxime. The Z-configuration of the nitrone double bond was established using NMR spectroscopic methods.
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References
M. H. Ghante and P. G. Jamkhande, J. Pharmacopuncture, 22 (2), 055 (2019).
W. Li, K. Sun, F. Hu, L. Chen, X. Zhang, F. Wang, and B. Yan, J. Biochem. Mol. Toxicol., 35 (3), e22658 (2020).
S. Arrous, I. Boudebouz, I. Parunov, E. Plotnikov, and O. Voronova, Chem. Nat. Compd., 55, 1094 (2019).
A. Gunther, E. Makuch, A. Nowak, W. Duchnik, L. Kucharski, R. Pelech, and A. Klimowicz, Molecules, 26, 3435 (2021).
V. R. Khairullina, A. Ya. Gerchikov, A. B. Safarova, R. R. Khalitova, A. Yu. Spivak, E. R. Shakurova, and V. N. Odinokov, Kinet. Catal., 52, 186 (2011).
J. L. C. Sousa, C. Goncalves, R. M. Ferreira, S. M. Cardoso, C. S. R. Freire, A. J. D. Silvestre, and A. M. S. Silva, Antioxidants, 10 (2), 148 (2021).
F. A. Villamena, A. Das, and K. M. Nash, Future Med. Chem., 4 (9), 1171 (2012).
R. A. Floyd, R. D. Kopke, C.-H. Choi, S. B. Foster, S. Doblas, and R. A. Towner, Free Radical Biol. Med., 45, 1361 (2008).
C. Oliveira, S. Benfeito, C. Fernandes, F. Cagide, T. Silva, and F. Borges, Med. Res. Rev., 38 (4), 1159 (2018).
M. Rosselin, B. Poeggeler, and G. Durand, Curr. Top. Med. Chem., 17, 1 (2017).
M. I. Ayuso, M. Chioua, E. Martinez-Alonso, E. Soriano, J. Montaner, J. Masjuan, D. J. Hadjipavlou-Litina, J. Marco-Contelles, and A. Alcazar, J. Med. Chem., 58, 6704 (2015).
S.-I. Murahashi and Y. Imada, Chem. Rev., 119 (7), 4684 (2019).
D. Roca-Lopez, T. Tejero, and P. Merino, J. Org. Chem., 79, 8358 (2014).
F. Ye, J. Xu, and M Ye, CN Pat. 104529814 A, Apr. 22, 2015.
J. H. Chang, US Pat. 4,405,357 A, Sept. 20, 1983.
H. Wang, J. C. Yang, and S. L. Buchwald, J. Am. Chem. Soc., 139, 8428 (2017).
I.-C. Sun, H.-K. Wang, Y. Kashiwada, J.-K. Shen, L. M. Cosentino, C.-H. Chen, L.-M. Yang, and K.-H. Lee, J. Med. Chem., 41, 4648 (1998).
L. Pohjala, S. Alakurtti, T. Ahola, J. Yli-Kauhaluoma, and P. Tammela, J. Nat. Prod., 72 (11), 1917 (2009).
O. B. Flekhter, O. Yu. Ashavina, E. I. Boreko, L. T. Karachurina, N. I. Pavlova, N. N. Kabal′nova, O. V. Savinova, F. Z. Galin, S. N. Nikolaeva, F. S. Zarudii, L. A. Baltina, and G. A. Tolstikov, Pharm. Chem. J., 36 (6), 303 (2002).
ACKNOWLEDGMENT
The work was performed on a State Task for UfIC, UFRC, RAS, topics Nos. 122031400260-7 and 122031400282-9. The spectral part of the research used equipment at the Khimiya CUC, UfIC, UFRC, RAS.
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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2022, pp. 900–904.
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Komissarova, N.G., Orlov, A.V., Malikova, K.A. et al. Nitrones Based on Pentacyclic Triterpenoids. Chem Nat Compd 58, 1069–1074 (2022). https://doi.org/10.1007/s10600-022-03868-7
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DOI: https://doi.org/10.1007/s10600-022-03868-7