Abstract
1-(Tetrahydrofuryl) derivatives of 5-timethylgermyl(silyl)uracil and uracil derivatives of 3-(5-nitro-2-furyl)acrylic acid, as well as 1-(γ-triethylgermyl)-and 1-(γ-triethoxysilyl)propylcarbamoyl-5-fluorouracils, were synthesized. Six of the 14 new investigated compounds have high cytotoxic activity in a culture of melanoma B16 cells. 5-Fluorouracil derivatives of 3-(5-nitro-2-furyl)acrylic acid display antitumorigenic activity with respect to lympholeucosis P388 that is comparable to the activity of ftorafur. It was demonstrated by electrochemical studies that the antitumorigenic activity is not determined by the redox properties of the investigated compounds.
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Literature Cited
M. Trušule, V. N. Verovsky, I. Avgustāne, E. Lukevics, T. S. Sheveleva, and S. P. Kolesnikov, Fifth International Symposium on Furan Chemistry: Abstracts, Riga, Sept. 21–23, 1988, Editorial Board: E. Lukevics (ed.-in-chief) et al., Institute of Organic Synthesis, Latvian SSR Acad. Sci., Riga (1988), p. 71.
Proceedings of the International Symposium on Ftorafur, Zinatne, Riga (1985).
é. Ya. Lukevits and A. E. Zablotskaya, The Silyl Method for the Synthesis of Nucleosides [in Russian], Zinatne, Riga (1985).
A. A. Lazdyn'sh, A. K. Veinberg, A. B. Sidorov, and S. A. Giller, USSR Author's Certificate No. 721,439; Byull. Izobret., No. 10 (1980).
é. Lukevits, M. Trushule, D. Zarinya, L. M. Ignatovich, and é. Liepin'sh, Zh. Obshch. Khim., 51, 827 (1981).
S. Ozaki, Y. Ike, H. Mizuno, K. Ishikawa, and H. Mori, Bull. Chem. Soc. Japan, 50, 2406 (1977).
J. P. Stradins, S. A. Hiller, R. A. Gavars, G. O. Reihmanis, and L. H. Baumane, Experientia, 18, Suppl., 607 (1977).
J. Stradins, R. Gavar, and L. Baumane, Electrochim. Acta, 28, 495 (1983).
Ya. P. Stradyn', R. A. Gavar, and L. Kh. Baumane, Izv. Akad. Nauk Latv. SSR, No. 2, 73 (1986).
R. A. Gavar, L. Kh. Baumane, Ya. P. Stradyn', and S. A. Giller, Khim. Geterotsikl. Soedin., No. 3, 324 (1974).
I. Arai and G. D. Daves, J. Chem. Soc., Chem. Commun., No. 1, 69 (1976).
S. Ya. Mel'nik, A. A. Bakhmedova, T. P. Nedorezova, I. V. Yartseva, O. S. Zhukova, Ya. V. Dobrynin, M. N. Preobrazhenskaya, S. P. Kolesnikov, V. Ya. Li, N. S. Rogozhin, O. M. Nefedov, é. V. Chekunova, and S. S. Marennikova, Bioorg. Khim., 11, 1248 (1985).
R. J. Geran, N. H. Greenborg, and M. M. Macdonald, Cancer Chemother. Rep., 3, 3 (1972).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1687–1694, December, 1991.
The authors thank S. P. Kolesnikov and T. S. Sheveleva (Institute of Organic Synthesis, Academy of Sciences of the USSR) for synthesizing and providing us with a sample of 5-trimethylgermyluracil.
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Trushule, M., Kupche, É., Augustane, I. et al. Synthesis, antitumorigenic activity, and electrochemical properties of uracil derivatives of the furan series. Chem Heterocycl Compd 27, 1358–1364 (1991). https://doi.org/10.1007/BF00515582
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DOI: https://doi.org/10.1007/BF00515582