Abstract
3β,28-Diacetoxylup-20(29)-en-30-oic acid (obtained via oxidation of betulin diacetate) enters the addition reaction with P—H-phosphonium salts (triarylphosphonium trifluoroacetates) under mild conditions to afford β-carboxyalkylphosphonium salts. Structure and composition of the resulting compounds were confirmed by NMR and IR spectroscopy, mass spectrometry, and elemental analysis.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
C. Dumontet, M. A. Jordan, Nat. Rev. Drug Discovery, 2010, 9, 790; DOI: https://doi.org/10.1038/nrd3253.
S. B. Kendall, Proc. R. Soc. Med. 1961, 54(5), 406.
S. Demkowicz, J. Rachon, M. Da′sko, W. Kozak, RSC Adv., 2016, 6, 7101; DOI: https://doi.org/10.1039/C5RA25446A.
I. van der Veen, J. de Boer, Chemosphere, 2012, 88, 1119; DOI: https://doi.org/10.1016/j.chemosphere.2012.03.067.
D. C. Rideout, T. Calogeropoulou, J. S. Jaworski, R. Dagnino, M. R. McCarthy, Anti-Cancer Drug Design, 1989, 4, 265.
M. P. Murphy, R. A. J. Smith, Annu. Rev. Pharmacol. Toxicol., 2007, 47, 629; DOI: https://doi.org/10.1146/annurev.pharmtox.47.120505.105110.
S. Fulda, L. Galluzzi, G. Kroemer, Nat. Rev. Drug Discovery, 2010, 9, 447; DOI: https://doi.org/10.1038/nrd3137.
M. T. Lin, M. F. Beal, Nature, 2006, 443, 787; DOI: https://doi.org/10.1038/nature05292.
M. Brownlee, Diabetes, 2005, 54, 1615; DOI: https://doi.org/10.2337/diabetes.54.6.1615.
D. Pathania, M. Millard, N. Neamati, Adv. Drug Delivery Rev., 2009, 61, 1250; DOI: https://doi.org/10.1016/j.addr.2009.05.010.
M. P. Murphy, Biochim. Biophys. Acta, 2008, 1777, 1028; DOI: https://doi.org/10.1016/j.bbabio.2008.03.029.
J. S. Modica-Napolitano, J. R. Aprille, Adv. Drug Delivery Rev., 2001, 49, 63; DOI: https://doi.org/10.1016/s0169-409x(01)00125-9.
M. Kurtoglu, T. J. Lampidis, Mol. Nutr. Food Res., 2009, 53, 68; DOI: https://doi.org/10.1002/mnfr.200700457.
T. J. Lampidis, Y. Hasin, M. J. Weiss, L. B. Chen, Biomed. Pharmacother., 1985, 39, 220.
J. Zielonka, J. Joseph, A. Sikora, M. Hardy, O. Ouari, J. Vasquez-Vivar, G. Cheng, M. Lopez, B. Kalyanaraman, Chem. Rev., 2017, 117, 10043; DOI: https://doi.org/10.1021/acs.chemrev.7b00042.
V. J. Adlam, J. C. Harrison, C. M. Porteous, A. M. James, R. A. Smith, M. P. Murphy, I. A. Sammut, FASEB J., 2005, 19, 1088; DOI: https://doi.org/10.1096/fj.05-3718com.
I. M. Fearon, S. P. Faux, J. Mol. Cell. Cardiol., 2009, 47, 372; DOI: https://doi.org/10.1016/j.yjmcc.2009.05.013.
J. A. Jara, V. Castro-Castillo, J. Saavedra-Olavarria, L. Peredo, M. Pavanni, F. Jana, M. E. Letelier, E. Parra, M. I. Becker, A. Morello, U. Kemmerling, J. D. Maya, J. Ferreira, J. Med. Chem., 2014, 57, 2440; DOI: https://doi.org/10.1021/jm500174v.
T. A. Prime, F. H. Blaikie, C. Evans, S. M. Nadtochiy, A. M. James, C. C. Dahm, D. A. Vitturi, R. P. Patel, C. R. Hiley, I. Abakumova, R. Requejo, E. T. Chouchani, T. T. Hurd, J. F. Garvey, C. T. Taylor, P. S. Brookes, R. A. J. Smith, M. P. Murphy, Proc. Natl. Acad. Sci. U. S. A., 106, 10764; DOI: https://doi.org/10.1073/pnas.0903250106.
M. Millard, D. Pathania, Y. Shabaik, L. Taheri, J. Deng, N. Neamati, PLoS One, 2010, 5, e13131; DOI: https://doi.org/10.1371/journal.pone.0013131.
O. V. Tsepaeva, A. V. Nemtarev, T. I. Abdullin, L. R. Grigor′eva, E. V. Kuznetsova, R. A. Akhmadishina, L. E. Ziganshina, H. K. Cong, V. F. Mironov, J. Nat. Prod., 2017, 80, 2232; DOI: https://doi.org/10.1021/acs.jnatprod.7b00105.
Pat RF 2665922 (2018); Byull. Izobr. Bulletin of Inventions], 2019, 25.
Y. Ye, T. Zhang, H. Yuan, D. Li, H. Lou, P. Fan, J. Med. Chem., 2017, 60, 6353; DOI: https://doi.org/10.1021/acs.jmedchem.7b00679.
A. Yu. Spivak, J. Keiser, M. Vargas, R. R. Gubaidullin, D. A. Nedopekina, E. R. Shakurova, R. R. Khalitova, V. N. Odinokov, Bioorg. Med. Chem., 2014, 22, 6297; DOI: https://doi.org/10.1016/j.bmc.2014.07.014.
I. S. Antipin, O. V. Tsepaeva, A. V. Nemtarev, T. I. Abdullin, L. R. Grigor′eva, E. V. Kuznetsova, R. A. Akhmadishina, V. F. Mironov, Eur. J. Clin. Inv., 2018, 48(S1), 97; DOI: https://doi.org/10.1111/eci.12926.
I. S. Antipin, D. V. Ponomaryov, L. R. Grigor′eva, T. I. Salikhova, R. Ali, T. Dang, O. V. Tsepaeva, A. V. Nemtarev, T. I. Abdullin, V. F. Mironov, Eur. J. Clin. Inv., 2019, 49(S1), 61; DOI: https://doi.org/10.1111/eci.13108.
A. Yu. Spivak, D. A. Nedopekina, R. R. Khalitova, R. R. Gubaidullin, V. N. Odinokov, Yu. P. Bel′skii, N. V. Bel′skaya, V. A. Khazanov, Med. Chem. Res., 2017, 26, 518; DOI: https://doi.org/10.1007/s00044-016-1771-z.
D. A. Nedopekina, R. R. Gubaidullin, V. N. Odinokov, P. V. Maximchik, B. Zhivotovsky, Yu. P. Bel’skii, V. A. Khazanov, A. V. Manuylova, V. Gogvadze, A. Yu. Spivak, Med. Chem. Commun., 2017, 8, 1934; DOI: https://doi.org/10.1039/c7md00248c.
O. V. Tsepaeva, A. V. Nemtarev, V. F. Mironov, J. Org. Chem., 2017, 53, 614 [O. V. Tsepaeva, A. V. Nemtarev, V. F. Mironov, Russ. J. Org. Chem, Engl. Transl.), 2017, 53, 621; DOI: https://doi.org/10.1134/S1070428017040212.
A. Yu. Spivak, D. A. Nedopekina, E. R. Shakurova, R. R. Khalitova, R. R. Gubaidullin, V. N. Odinokov, Yu. P. Bel′skii, N. V. Bel′skaya, S. A. Stankevich, E. V. Korotkaya, V. A. Khazanov, Russ. Chem. Bull., 2013, 62, 188; DOI: https://doi.org/10.1007/s11172-013-0028-y.
O. V. Tsepaeva, A. V. Nemtarev, T. I. Abdullin, E. V. Kuz netsova, V. F. Mironov, Russ. J. Gen. Chem., 2018, 88, 1944]; DOI: https://doi.org/10.1134/S1070363218090335.
E. Chrobak, E. Bebenek, M. Kadela-Tomanek, M. Latocha, C. Jelsch, E. Wenger, S. Boryczka, Molecules, 2016, 21, 1123; DOI: https://doi.org/10.3390/molecules21091123.
N. R. Khasiyatullina, V. F. Mironov, S. K. Gumerova, A. D. Voloshina, A. S. Sapunova, Mendeleev Commun., 2019, 29, 435; DOI: https://doi.org/10.1016/j.mencom.2019.07.027.
N. R. Khasiyatullina, A. M. Vazykhova, Y. K. Voronina, V. F. Mironov, Russ. J. Gen. Chem., 2017, 87, 1934; DOI: https://doi.org/10.1134/S1070363217090079.
V.I. Galkin, Yu. V. Bakhtiyarova, N. A. Polezhaeva, I. V. Galkina, R. A. Cherkasov, D. B. Krivolapov, A. T. Gubaidullin, I. A. Litvinov, Russ. J. Gen. Chem., 2002, 72, 376; DOI: https://doi.org/10.1023/A:1015435432082.
V. I. Galkin, Yu. V. Bakhtiyarova, N. A. Polezhaeva, I. V. Galkina, R. A. Cherkasov, D. B. Krivolapov, A. T. Gubaidullin, I. A. Litvinov, Russ. J. Gen. Chem., 2002, 72, 384; DOI: https://doi.org/10.1023/A:1015487416152.
L. Pohjala, S. Alakurtti, T. Ahola, J. Yli-Kauhaluoma, P. Tammela, J. Nat. Prod., 2009, 72, 1917; DOI: https://doi.org/10.1021/np9003245.
Author information
Authors and Affiliations
Corresponding author
Additional information
Synthetic part of the present study was financially supported by the Russian Foundation for Basic Research (Project No. 19-33-90275), spectral studies were supported by the Ministry of Science and Higher Education of the Russian Federation (subsidies allocated to Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences” (FRS KSC RAS) and Kazan Federal University for the state assignements in the field of scientific activities). The authors gratefully acknowledge the Assigned Spectral Analytical Center for Study of Structure, Properties and Composition of Substances and Materials of the KSC RAS.
Based on the materials of the International Markovnikov Congress on Organic Chemistry (June 21-28, 2019, Moscow-Kazan, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0487—0491, March, 2020.
Rights and permissions
About this article
Cite this article
Ponomaryov, D.V., Grigor´eva, L.R., Nemtarev, A.V. et al. Synthesis of C-29-phosphonium derivatives of 3,28-diacetoxylup-20(29)-en-30-oic acid. Russ Chem Bull 69, 487–491 (2020). https://doi.org/10.1007/s11172-020-2787-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-020-2787-6