Статья
2020
Synthesis and Cytotoxicity of Selenium-Containing Dienones
D. M. Gusev, A. S. Bunev, A. A. Golovanov
Российский журнал общей химии
https://doi.org/10.1134/S1070363220020085
Abstract / Full Text
The nucleophilic addition of benzoselenol occurs regioselectively at the β-carbon of the triple bond of 1,5-disubstituted pent-2-ene-4-yne-1-ones, pent-4-ene-2-yne-1-ones and pent-1-ene-4-yne-3-ones. The resulting selenium-containing conjugated dienones exhibit pronounced cytotoxicity against some tumor cell lines.
Author information
- Togliatti State University, 445020, Togliatti, RussiaD. M. Gusev, A. S. Bunev & A. A. Golovanov
References
- Organoselenium Chemistry: Synthesis and Reactions, Wirth, T., Ed., Weinheim: Wiley VCH Verlag GmbH, 2012. https://doi.org/10.1002/9783527641949
- Rocha, J.B.T., Piccoli, B.C., and Oliveira, C.S., Arkivoc, 2017, vol. ii, p. 457. https://doi.org/10.24820/ark.5550190.p009.784
- Młochowski, J., Kloc, K., Lisiak, R., Potaczek, P., and Wójtowicz, H., Arkivoc, 2007, vol. vi, p. 14. https://doi.org/10.3998/ark.5550190.0008.603
- Petragnani, N., Stefani, H.A., and Valduga, C.J., Tetrahedron, 2001, vol. 57, no. 8, p. 1411. https://doi.org/10.1016/S0040-4020(00)01033-4
- Nowak, P., Saluk-Juszczak, J., Olas, B., Kołodziejczyk, J., and Wachowicz, B., Cell. Mol. Biol. Lett., 2006, vol. 11, no. 1, p. 1. https://doi.org/10.2478/s11658-006-0001-y
- Wang, L., Yang, Z., Fu, J., Yin, H., Xiong, K., Tan, Q., Jin, H., Li, J., Wang, T., Tang, W., Yin, J., Cai, G., Liu, M., Kehr, S., Becker, K., and Zeng, H., Free Rad. Biol. Med., 2012, vol. 52, no. 5, p. 898. https://doi.org/10.1016/j.freeradbiomed.2011.11.034
- Brozmanová, J., Mániková, D., Vlčková, V., Chovanec, M., Arch. Toxicol., 2010, vol. 84. no. 12, p. 919. https://doi.org/10.1007/s00204-010-0595-8
- Tiekink, E.R.T., Dalton Trans., 2012, vol. 41. no. 21, p. 6390. https://doi.org/10.1039/C2DT12225A
- Saluk-Juszczak, J., Wachowicz, B., Wójtowicz, H., Kloc, K., Bald, E., and Glowacki, R., Cell. Biol. Toxicol., 2006, vol. 22, no. 5, p. 323. https://doi.org/10.1007/s10565-006-0091-3
- Sakurai, T., Kanayama, M., Shibata, T., Itoh, K., Kobayashi, A., Yamamoto, M., and Uchida, K., Chem. Res. Toxicol., 2006, vol. 19, no. 9, p. 1196. https://doi.org/10.1021/tx0601105
- Golovanov, A.A., Gusev, D.M., Vologzhanina, A.V., Bekin, V.V., and Pisareva, V.S., Russ. J. Org. Chem., 2014, vol. 50, no. 1, p. 13. https://doi.org/10.1134/S1070428014010035
- Golovanov, A.A., Gusev, D.M., and Zlotskii, S.S., Russ. J. Org. Chem., 2016, vol. 52, no. 8, p. 1205. https://doi.org/10.1134/S1070428016080194
- Tanini, D., Scarpelli, S., Ermini, E., and Capperucci, A., Adv. Synth Catal., 2019, vol. 361, no. 10, p. 2337. https://doi.org/10.1002/adsc.201900168
- Battistelli, B., Lorenzo, T., Tiecco, M., and Santi, C., Eur. J. Org. Chem., 2011, no. 10, p. 1848. https://doi.org/10.1002/ejoc.201100045
- Ananikov, V.P., Malyshev, D.A., Beletskaya, I.P., Aleksandrov, G.G., and Eremenko, I.L., J. Organomet. Chem., 2003, vol. 679, no. 2, p. 162. https://doi.org/10.1016/S0022-328X(03)00546-1
- Kawaguchi, S., Kotani, M., Atobe, S., Nomoto, A., Sonoda, M., and Ogawa, A., Organometallics, 2011, vol. 30, no. 24, p. 6766. https://doi.org/10.1021/om200663k
- Ishii, A., Kamon, H., Murakami, K., and Nakata, N., Eur. J. Org. Chem., 2010, no. 9, p. 1653. https://doi.org/10.1002/ejoc.200901408
- Nakata, N., Ikeda, T., and Ishii, A., Inorg. Chem., 2010, vol. 49, no. 17, p. 8112. https://doi.org/10.1021/ic1011742
- Kolos, N.N. and Komykhov, S.A., Chem. Heterocycl. Compd., 2019, vol. 55, nos. 4–5, p. 312. https://doi.org/10.1007/s10593-019-02460-2
- Golovanov, A.A., Bekin, V.V., Odin, I.S., Chertov, A.Yu., Grigor’eva, O.B., and Pisareva, V.S., Russ. J. Org. Chem., 2015, vol. 51, no. 12, p. 1688. https://doi.org/10.1134/S1070428015120039
- Statsyuk, V.E., Krasnov, V.L., Korshunov, S.P., and Bodrikov, I.V., Zh. Org. Khim., 1983, vol. 19, no. 3, p. 468.
- Golovanov, A.A., Latypova, D.R., Bekin, V.V., Pisareva, V.S., Vologzhanina, A.V., and Dokichev, V.A., Russ. J. Org. Chem., 2013, vol. 49, no. 9, p. 1264. https://doi.org/10.1134/S1070428013090030
- Vologzhanina, A.V., Golovanov, A.A., Gusev, D.M., Odin, I.S., Apreyan, R.A., and Suponitsky, K.Yu., Crystal Growth Design, 2014, vol. 14, no. 9, p. 4402. https://doi.org/10.1021/cg500512e
- Utekhina, N.V., Korzhova, N.V., Kazantseva, V.M., Surov, Yu.N., Orlov, V.D., and Korshunov, S.P., Zh. Obshch. Khim., 1988, vol. 58, no. 3, p. 692.
- Chinta, B.S. and Baire, B., J. Org. Chem., 2015, vol. 80, no. 20, p. 10208. https://doi.org/10.1021/acs.joc.5b01780
- Marvell, E.N., Caple, G., Delphey, C., Platt, J., Polston, N., and Tashiro, J., Tetrahedron, 1973, vol. 29, no. 23, p. 3797. https://doi.org/10.1016/0040-4020(73)80197-8
- Attenburrow, J., Cameron, A.F.B., Campton, J.H., Evans, R.M., Jansen, A.B.A., and Walker, T., J. Chem. Soc., 1952, p. 1094. https://doi.org/10.1039/JR9520001094
- Panov, A.M., Ratovskii, G.V., Kipovich, T.V., Filippova, T.M., and Buzilova, S.R., Zh. Obshch. Khim., 1982, vol. 52, no. 8, p. 1761.