Abstract
A new method was developed for the synthesis of silicon-and germanium-containing acetylfurans and acetylthiophene by metallation of 2-acetylfuran or 2-acetylthiophene with n-BuLi at low temperature after protection of the carbonyl group with lithium N-methylpiperazide and reaction of the lithium derivative with various trialkyl-, alkylphenyl-, and cycloalkylchlorosilanes or trialkylchloro(bromo)germanes. The cytotoxic activity of the new compounds was studied, and it was established that the silicon-and germanium-containing acetylfurans and acetylthiophenes are substances with low toxicity (LD50 312->2000 mg/kg) and have low cytotoxicity toward HT-1080 and MG-22A tumor cells.
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References
E. Lukevics and L. Ignatovich, Heterocycles on the World Medicine Market [in Russian], Institute of Organic Synthesis, Latvian Academy of Sciences, Riga (1992).
S. Eguchi, Bioactive Heterocycles, Springer, 2006.
E. Lukevics and L. Ignatovich, in: M. Gielen and E. R. T. Tiekink (editors), Metallotherapeutic Drugs & Metal-based Diagnostic Agents. The Use of Metals in Medicine, John Wiley & Sons, Ltd., Chichester (2005), p. 81.
E. Lukevics and L. Ignatovich, in: M. Gielen and E. R. T. Tiekink (editors), Metallotherapeutic Drugs & Metal-based Diagnostic Agents. The Use of Metals in Medicine, John Wiley & Sons, Ltd., Chichester, 2005, p. 278.
L. Ignatovich, D. Zarina, I. Shestakova, S. Germane, and E. Lukevics, in: N. Auner and J. Weis (editors), Organosilicon Chemistry. VI. From Molecules to Materials, Wiley-VCH, Weinheim (2005), p. 278.
Yu. Mel’nik, M. Vorona, G. Veinberg, J. Popelis, L. Ignatovich, and E. Lukevics, Khim. Geterotsikl. Soedin., 834 (2005). [Chem. Heterocycl. Comp., 41, 718 (2005)].
J. A. Joule and K. Mills, Heterocyclic Chemistry, Blackwell Science Ltd. (2000), p. 273.
J. A. Joule and K. Mills, Heterocyclic Chemistry, Blackwell Science Ltd. (2000), p. 296.
D. C. Bowman, Chem. Educator, 9, 163 (2004).
G. Ciranni and S. Clementi, Tetrahedron Lett., 12, 3833 (1971).
W. P. Weber, Silicon Reagents for Organic Synthesis, Springer Verlag, Berlin, Heidelberg, New York (1983), p. 114.
R. A. Benkeser and R. B. Currie, J. Am. Chem. Soc., 70, 1780 (1948).
E. Lukevics, L. Ignatovich, I. Sleiksha, V. Muravenko, I. Shestakova, S. Belyakov, and J. Popelis, Appl. Organometal. Chem., 20, 454 (2006).
US Dept. of Health and Human Services, Guidance Document on Using in vitro Data to Estimate in vivo Starting Doses for Acute Toxicity, National Institute of Health (2001).
G. Veinberg, M. Vorona, I. Shestakova, I. Kanepe, O. Zharkova, R. Mezapuke, I. Turovskis, I. Kalvinsh, and E. Lukevics, Bioorg. Med. Chem., 8, 1033 (2000).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 192–199, February, 2007.
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Lukevics, E., Ignatovich, L., Sleiksha, I. et al. A new method for the synthesis of silicon-and germanium-containing 2-acetylfurans and 2-acetylthiophenes. Chem Heterocycl Compd 43, 143–150 (2007). https://doi.org/10.1007/s10593-007-0024-y
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DOI: https://doi.org/10.1007/s10593-007-0024-y