Symmetric and asymmetric derivatives of (–)-convolutamydine and analogs in which 3-hydroxy-2-oxindole fragments were conjugated through a 2-oxopropyl linker were synthesized. Monobromoxindole 10 from the reaction of (S)-3-hydroxy-3-(2-oxopropyl)indolin-2-one and 5-bromoisatin exhibited the greatest cytotoxicity of all tested compounds with CC50 = 0.197 mM in acutely infected MT-4 cells. The cytotoxicities of dibromo derivatives 7 and 9 decreased as compared to 10 to CC50 = 0.205 and 0.245 mM, respectively.
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References
S. Peddibhotla, Curr. Bioact. Compd., 5, 20 (2009).
A. Kumar and S. S. Chimni, RSC Adv., 2, 9748 (2012).
Y. Kamano, H. Zhang, Y. Ichihara, H. Kizu, K. Komiyama, and G. R. Pettit, Tetrahedron Lett., 36, 2783 (1995).
H. Zhang, Y. Kamano, Y. Ichihara, H. Kizu, K. Komiyama, H. Itokawa, and G. R. Pettit, Tetrahedron, 51, 5523 (1995).
G. S. M. Figueiredo, R. S. Zardo, B. V. Silva, F. A. Violante, A. C. Pinto, and P. D. Fernandes, Pharmacol., Biochem. Behav., 103, 431 (2013).
H. M. S. Kumar, L. Herrmann, and S. B. Tsogoeva, Bioorg. Med. Chem. Lett., 30, 127514 (2020)
M. A. Kabeshov, O. Kysilka, L. Rulisek, Y. V. Suleimanov, M. Bella, A. V. Malkov, and P. Kocovsky, Chem. Eur. J., 21 (34), 12203 (2015).
S. Wei, B. Schmid, F. Z. Macaev, S. N. Curlat, A. V. Malkov, and S. B. Tsogoeva, Asymmetric Catal., 2, 1 (2015).
A. V. Malkov, M. A. Kabeshov, M. Bella, O. Kysilka, D. A. Malyshev, K. Pluhackova, and P. Kocovsky, Org. Lett., 9, 5473 (2007).
F. Z. Manaev and V. S. Pogrebnoi, Chem. Nat. Compd., 52, 86 (2016).
S. N. Curlat, A. N. Barba, V. V. Boldescu, C. Pannecouque, and F. Z. Macaev, Chem. Nat. Compd., 55, 269 (2019).
O. I. El-Sabbagh, M. M. Baraka, S. M. Ibrahim, C. Pannecouque, G. Andrei, R. Snoeck, J. Balzarini, and A. A. Rashad, Eur. J. Med. Chem., 44, 3746 (2009).
M. Witvrouw, H. Weigold, C. Pannecouque, D. Schols, E. De Clercq, and G. Holan, J. Med. Chem., 43, 778 (2000).
M. Witvrouw, D. Schols, G. Andrei, R. Snoeck, M. Hosoya, R. Pauwels, J. Balzarini, and E. De Clercq, Antiviral Chem. Chemother., 2, 171 (1991).
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The work was financially supported by Applied Research Project 20.80009.5007.17 of the National Agency for Research and Development of Moldova.
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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2021, pp. 440–443.
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Bilan, D.Y., Sucman, N.S., Radul, O.M. et al. Synthesis of (–)-Convolutamydine a Derivatives and Analogs. Chem Nat Compd 57, 516–520 (2021). https://doi.org/10.1007/s10600-021-03400-3
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DOI: https://doi.org/10.1007/s10600-021-03400-3