Abstract
A method has been developed for the preparation of a new type of dispiro derivative, 5''-bromo-2-[(4-chlorophenyl)sulfanyl]-1'-methyl-1,4'-diphenyldispiro[imidazole-4,3'-pyrrolidine-2',3''-indoline]-2'',5(1H)-dione, starting from 2-thiohydantoin and using a 1,3-dipolar cycloaddition reaction. The configuration of the target dispiro derivative was unambiguously established by physicochemical methods.
Similar content being viewed by others
REFERENCES
National Cancer Institute. Center for Cancer Research. Clinical Trials, USA, 2019.
Sun, Yu., Sun, Yi, Wenger, L., Rutter, J.L., Brinckerhoff, C.E., and Cheung, H.S., J. Biol. Chem., 1999, vol. 274, p. 11535. https://doi.org/10.1074/jbc.274.17.11535
Cummins, J.M., Rago, C., Kohli, M., Kinzler, K.W., Lengauer, C., and Vogelstein, B., Nature, 2004, vol. 428, p. 6982. https://doi.org/10.1038/nature02501
Bartel, F., Meye, A., Würl, P., Kappler, M., Bache, M., Lautenschläger, C., Grünbaum, U., Schmidt, H., and Taubert, H., Int. J. Cancer, 2001, vol. 95, p. 168. https://doi.org/10.1002/1097-0215(20010520)95:3<168::aid-ijc1029>3.0.co;2-a
Bueso-Ramos, C.E., Yang, Y., McCown, P., Stass, S., and Albitar, M., Blood, 1993, vol. 82, p. 2617. https://doi.org/10.1182/blood.V82.9.2617.2617
Ivanenkov, Y.A., Vasilevski, S.V., Beloglazkina, E.K., Kukushkin, M.E., Machulkin, A.E., Veselov, M.S., Chufarova, N.V., Chernyagina, E.S., Vanzcoola, A.S., Zyk, N.V., Skvortsov, D.A., Khutornenko, A.A., Rusanov, A.L., Tonevitsky, A.G., Dontsova, O.A., and Majouga, A.G., Bio. Med. Chem. Lett., 2015, vol. 25, p. 404. https://doi.org/10.1016/j.bmcl.2014.09.070
Dlin, E.A., Averochkin, G.M., Finko, A.V., Vorobyeva, N.S., Beloglazkina, E.K., Zyk, N.V., Ivanenkov, Y.A., Skvortsov, D.A., Koteliansky, V.E., and Majouga, A.G., Tetrahedron Lett., 2016, vol. 57, p. 5501. https://doi.org/10.1016/j.tetlet.2016.10.102
Jung, M.E., Ouk, S., Yoo, D., Sawyers, C.L., Chen, C., Tran, C., and Wongvipat, J., J. Med. Chem., 2010, vol. 53, p. 2779. https://doi.org/10.1021/jm901488g
Carreaux, F., US Patent no. 2010216855 A1, 2010. https://patents.google.com/patent/US20100216855A1/en
Cheng, S.-W., Tseng, M.-C., Lii, K.-H., Lee, C.-R., and Shyu, S.-G., Chem. Commun., 2011, vol. 47, p. 5599. https://doi.org/10.1039/C1CC11067E
He, J., Ouyang, G., Yuan, Z., Tong, R., Shi, J., and Ouyang, L., Molecules, 2013, vol. 18, p. 5142. https://doi.org/10.3390/molecules18055142
Kuznetsova, O.Y., Antipin, R.L., Udina, A.V., Krasnovskaya, O.O., Beloglazkina, E.K., Terenin, V.I., Koteliansky, V.E., Zyk, N.V., and Majouga, A.G., J. Heterocycl. Chem., 2016, vol. 53, p. 1570. https://doi.org/10.1002/jhet.2464
ACKNOWLEDGMENTS
The authors are grateful to Thermo Fisher Scientific and MS Analitika (Moscow) and personally Prof. A.A. Makarov for the mass spectrometric equipment provided for our use for performing the present work.
Funding
The work was performed by the State Order for the Lomonosov Moscow State University.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
Finko, A.V., Stepanova, S.P., Kukushkin, M.E. et al. A Novel S-Arylated Dispiro Derivative of 2-Thiohydantoin. Russ J Org Chem 56, 946–948 (2020). https://doi.org/10.1134/S1070428020050322
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428020050322