New highly cytotoxic 3-aminopropyl derivatives of 2-dimethylsilyl-5-trialkylgermylfuran (IC50 1−3 μg⋅ml−1) have been prepared by hydrosilylation of heterocyclic N-allylamines with the corresponding hydrosilane in the presence of Speier’s catalyst. The influence of the amine structure and alkyl substituent at the germanium atom on the cytotoxicity has been investigated.
Similar content being viewed by others
References
A. Kleemann, J. Engel, B. Kutscher, and D. Reichert, Pharmaceutical Substances, Thieme, Stuttgart-New York, 2009.
D. A. Erlanson and W. Jahnke (editors), Fragment-based Approaches in Drug Discovery, Wiley-VCH: Weinheim, 2006.
J. J. McGuire, Curr. Pharm. Des., 9, 2593 (2003).
H. S. Rasmussen and P. P. McCann, Pharmacol. Ther., 75, 69 (1997).
B. Moy, P. Kirkpatrick, S. Kar, and P. Gross, Nature Rev. Drug Discov., 6, 431 (2007).
M. G. Voronkov, G. I. Zelchan, and E. Lukevics, Silicon and Life, [in Russian], Zinatne, Riga, 1978.
E. Lukevics, V. Lūse, I. Zicmane, E. Liepinš, M. Trušule, S. Ģērmane, I. Augustāne, V. N. Verovsky, N. G. Prodanchuk, S. E. Deineka, and V. N. Nivalov, Khim. Geterotsikl. Soedin., 1653 (1991). [Chem. Heterocycl. Comp., 27, 1328 (1991)].
L. Ignatovich, V. Muravenko, I. Shestakova, I. Domrachova, J. Popelis, and E. Lukevics, Appl. Organomet. Chem., 2009, DOI 10.1002, aoc, 1538.
E. Lukevics and L. M. Ignatovich, Appl. Organomet. Chem., 6, 113 (1992).
R. Tacke and S. A. Wagner, in: Z. Rappoport and Y. Apeloig (editors), The Chemistry of Organic Silicon Compounds, John Wiley & Sons, Chichester, 1998, vol. 2, p. 2363.
E. Lukevics and L. Ignatovich, in: M. Gielen and E. R. T. Tiekink (editors), Metallotherapeutic Drugs and Metal-Based Diagnostic Agents. The Use of Metals in Medicine, John Wiley & Sons, 2005, Ch.5, p. 83.
A. K. Franz, Curr. Opinion Drug Discov. and Dev., 10, 654 (2007).
E. Lukevics, L. Ignatovich, Yu. Goldberg, F. Polyak, A. Gaukhman, S. Rozite, and J. Popelis, J. Organomet. Chem., 11, 348 (1988).
R. I. Freshney, Culture of Annimal Cells (A Manual of Basic Technique), Wiley-Liss, New York, 1994, p. 29.
D. I. Fast, R. C. Lynch and R. W. Leu, J. Leucocyt. Biol., 52, 255 (1992).
Guidance Document on Using in vitro Data to Estimate in vivo Starting Doses for Acute Toxicity, NIH Publ. N01-4500 (2001), p. 12 . http://www.epa.gov/hpv/pubs/general/nih2001b.pdf
Author information
Authors and Affiliations
Corresponding author
Additional information
Deceased. (E. Lukevics)
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1791–1799, November, 2009.
Rights and permissions
About this article
Cite this article
Ignatovich, L., Romanovs, V., Shestakova, I. et al. Synthesis and biological activity of new 2-[(3-aminopropyl)dimethyl-silyl]-5-trialkylgermylfurans. Chem Heterocycl Comp 45, 1441–1448 (2009). https://doi.org/10.1007/s10593-010-0447-8
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-010-0447-8