Substituted ureides and thioureides of maleopimaric acid (MPA) were synthesized via two methods: reaction of MPA chloride with monosubstituted ureas and thioureas and reaction of MPA chloride with KSCN and then in situ with various amines. The structures of all synthesized compounds were proven using NMR spectroscopy, X-ray crystal structure analyses, and mass spectroscopy.
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L. Rosu, F. Mustata, D. Rosu, C.-D. Varganici, I. Rosca, and T. Rusu, Prog. Org. Coat., 151, 106008 (2021).
Sh. Wang, X. Yang, Zh. Li, X. Xu, H. Liu, D. Wang, H. Min, and Sh. Shang, Compos. Sci. Technol., 198, 108272 (2020).
M. P. Bei, Al. An. Muravskii, An. Al. Muravskii, D. S. Chepeleva, N. V. Puchkova, and A. P. Yuvchenko, Vestsi Akad. Navuk Belarusi, Ser. Khim. Navuk, 56 (3), 293 (2020).
Zh. Li, J. Cheng, X. Yang, Sh. Shang, H. Liu, Zh. Song, X. Xu, and L. Ma, Int. J. Biol. Macromol., 150, 1 (2020).
J. Song, H. Kim, W. Jae, T. Kim, C. M. Futalan, and J. Kim, Carbon, 165, 55 (2020).
G. F. Vafina, M. D. Khanova, S. A. Meshcheryakova, and A. K. Bulgakov, Chem. Nat. Compd., 55, 868 (2019).
G. F. Vafina, M. D. Khanova, Ya. L. Esaulkova, E. O. Sinegubova, A. V. Slita, and V. V. Zarubaev, Chem. Nat. Compd., 57, 323 (2021).
B. T. Purwanto, World J. Pharm. Res., 7 (07), 56 (2018), https://doi.org/10.20959/wjpr20187-11482.
W. H. Schuller and L. V. Lawrence, J. Chem. Eng. Data, 12, 267 (1967).
M. E. Aboutabl, R. M. Hassan, A. A.-S. El-Azzouny, M. N. Aboul-Enein, and W. H. Abd-Allah, Bioorg. Chem., 94, 103473 (2020).
Agilent (2012), CrysAlisPro. Agilent Technologies, Yarnton, Oxfordshire, England.
G. M. Sheldrick, Acta Cryst., Sect. A: Found. Crystallogr., 64 (1), 112 (2008).
Acknowledgment
The work was performed on State Task Topic No. 122031400260-7, “Synthesis of biologically active compounds based on natural compounds. Creation of ecologically clean materials and technologies.” Spectra (XSA, NMR, IR, mass) were recorded on equipment of the Khimiya CUC, UfIC, RAS, and Agidel′ RCUC, UFRC, RAS. We thank E. S. Meshcheryakova and L. M. Khalilov (Inst. Petrochem. Catal., RAS) for performing the XSA of a crystal of 4e.
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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2022, pp. 887–892.
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Vafina, G.F., Khanova, M.D. & Lobov, A.N. Synthesis of New Substituted Ureides and Thioureides Based on Maleopimaric Acid. Chem Nat Compd 58, 1055–1061 (2022). https://doi.org/10.1007/s10600-022-03865-w
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DOI: https://doi.org/10.1007/s10600-022-03865-w