Abstract
The reaction of maleopimaric and dihydroquinopimaric acid chlorides with potassium thiocyanate gave the corresponding acyl isothiocyanates which were treated with primary amines and L-amino acid methyl esters to afford new diterpenoid thiourea derivatives.
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REFERENCES
Faustino, C., Neto, I., Fonte, P., and Macedo, A., Curr. Pharm. Des., 2018, vol. 24, p. 4362. https://doi.org/10.2174/1381612825666190112162817
Hou, W., Zhang, G., Luo Zhi, Li Di, Ruan, H., Ruan, B.H., Su, L., and Xu, H., Bioorg. Med. Chem. Lett., 2017, vol. 27, p. 5382. https://doi.org/10.1016/j.bmcl.2017.11.014
González, M.A., Correa-Royero, J., Agudelo, L., Mesa, A., and Betancur-Galvis, L., Eur. J. Med. Chem., 2009, vol. 44, p. 2468. https://doi.org/10.1016/j.ejmech.2009.10.010
Sepúlveda, B., Astudillo, L., Rodríguez, J.A., Yáfiez, T., Theoduloz, C., and Schmeda-Hirschmann, G., Pharm. Res., 2005, vol. 52, p. 429. https://doi.org/10.1016/j.phrs.2005.06.004
Kazakova, O.B., Smirnova, I.E., Tkhu, H.D.T., Nguen, T.T., Apryshko, G.N., Zhukova, O.S., Medvedeva, N.I., Nazyrov, T.I., Tret’yakova, E.V., Chudov, I.V., Ismagilova, A.F., Suponitsky, K.Yu., Kazakov, D.V., Safarov, F.E., and Tolstikov, G.A., Russ. J. Bioorg. Chem., 2013, vol. 39, p. 202. https://doi.org/10.1134/S1068162013020088
Justino, G.A.C., Correia, C.F., Mira, L., Dos Santos, R.M.B., Simones, J.A.M., Silva, A.M., Santos, C.L., and Gigante, B.R., J. Agric. Food Chem., 2006, vol. 54, p. 342. https://doi.org/10.1021/jf052062k
Tolstikov, G.A., Tolstikova, T.G., Shul’ts, E.E., Tolstikov, S.E., and Khvostov, M.V., Smolyanye kisloty khvoinykh Rossii. Khimiya, farmakologiya (Rosin Acids from Russian Coniferous Plants. Chemistry and Pharmacology), Novosibirsk: GEO, 2011.
Kazakova, O.B., Tret’yakova, E.V., Smirnova, I.E., Spirikhin, L.V., Tolstikov, G.A., Chudov, I.V., Bazekin, G.V., and Ismagilova, A.F., Russ. J. Bioorg. Chem., 2010, vol. 36, p. 257. https://doi.org/10.1134/S1068162010020160
Tretyakova, E.V., Smirnova, I.E., Salimova, E.V., Pashkova, T.M., Kartashova, O.L., Odinokov, V.N., and Parfenova, L.V., Russ. J. Bioorg. Chem., 2017, vol. 43, p. 317. https://doi.org/10.1134/S1068162017020169
Tretyakova, E.V., Smirnova, I.E., Salimova, E.V., and Odinokov, V.N., Bioorg. Med. Chem., 2015, vol. 23, p. 6543. https://doi.org/10.1016/j.bmc.2015.09.006
Tretyakova, E.V., Salimova, E.V., Parfenova, L.V., Yunusbaeva, M.M., Dzhemileva, L.U., D’yakonov, V.V., and Dzhemilev, U.M., Anticancer Agents Med. Chem., 2019, vol. 19, p. 1172. https://doi.org/10.2174/1871520619666190404100846
Kazakova, O.B., Tret’yakova, E.V., Kukovinets, O.S., Tolstikov, G.A., Nazyrov, T.I., Chudov, I.V., and Ismagilova, A.F., Russ. J. Bioorg. Chem., 2010, vol. 36, p. 762. https://doi.org/10.1134/S1068162010060130
Tret’yakova, E.V., Smirnova, I.E., Kazakova, O.B., Yavorskaya, N.P., Golubeva, I.S., Zhukova, O.S., Pugacheva, R.B., Apryshko, G.N., and Poroikov, V.V., Bioorg. Med. Chem., 2014, vol. 22, p. 6481. https://doi.org/10.1016/j.bmc.2014.09.030
Kovaleva, K., Oleshko, O., Mamontova, E., Yarovaya, O., Zakharova, O., Zakharenko, A., Kononova, A., Dyrkheeva, N., Cheresiz, S., Pokrovsky, A., Lavrik, O., and Salakhutdinov, N., J. Nat. Prod., 2019, vol. 82, p. 2443. https://doi.org/10.1021/acs.jnatprod.8b01095
Huang, X.-Ch., Wang, M., Pan, Y.-M., Tian, X.-Y., Wang, H.-Sh., and Zhang, Y., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 5283. https://doi.org/10.1016/j.bmcl.2013.08.005
Huang, X.-Ch., Wang, M., Pan, Y.-M., Yao, G.-Y., Wang, H.-Sh., Tian, X.-Y., Qin, J.-K., and Zhang, Y., Eur. J. Med. Chem., 2013, vol. 69, p. 508. https://doi.org/10.1016/j.ejmech.2013.08.055
Huang, X., Huang, R., Liao, Z., Pan, Y., Gou, Sh., and Wang, H., Eur. J. Med. Chem., 2016, vol. 108, p. 381. https://doi.org/10.1016/j.ejmech.2015.12.008
Tret’yakova, E.V., Russ. J. Org. Chem., 2021, vol. 57, p. 391. https://doi.org/10.1134/S1070428021030106
Flekhter, O.B., Smirnova, I.E., Tret’yakova, E.V., Tolstikov, G.A., Savinova, O.V., and Boreko, E.I., Russ. J. Bioorg. Chem., 2009, vol. 35, p. 385. https://doi.org/10.1134/S1068162009030157
Herz, W., Blakstone, R.C., and Nair, M.G., J. Org. Chem., 1967, vol. 32, p. 2292.
Zalkov, L.U., Ford, R.A., and Cutney, J.P., J. Org. Chem., 1962, vol. 27, p. 3535.
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This study was performed in the framework of state assignment no. AAAA-A20-120012090023-8.
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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 6, pp. 852–859 https://doi.org/10.31857/S0514749221060070.
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Tret’yakova, E.V. Synthesis and Modification of Isothiocyanate Derivatives of Maleopimaric and Dihydroquinopimaric Acids. Russ J Org Chem 57, 930–935 (2021). https://doi.org/10.1134/S1070428021060075
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DOI: https://doi.org/10.1134/S1070428021060075