A series of 16 cyclopentane and hydrindane 2-acetyl-1,3-diones were synthesized. The hemolytic properties of these compounds were studied on erythrocytes of white mongrel mice at various pH values. Bifosin (bifonazole), saponin (Fluka, BioChemika, Germany), and triton X-100 were used as reference preparations. It was found that 2-acetylcyclopent-4-ene-1,3-dione (III), 2-acetyl-4-chlorocyclopent-4-ene-1,3-dione (VI), 2-acetyl-4-bromocyclopent-4-ene-1,3-dione (VII), and 2-acetyl-4,5-dichlorocyclopent-4-ene-1,3-dione (IX) exhibited rather strong (as compared to bifosin and saponin) hemolytic action on erythrocytes. The effect was more pronounced at pH 7.4 (ED50 = 0.42 – 4.9 μg/mL) than at pH 6.0 (ED50 = 6.5 – 39.9 μg/mL). It was also established that triketones I, XI, and XV exhibited selective hemolytic effects at pH 6.0. However, the level of their activity was not sufficiently high (ED50 = 55.6 – 72.6 μg/mL). Some of the studied compounds are of interest as potential cytotoxic and antitumor agents.
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References
X.-C. Li, D. Ferreira, M. R. Jacob, et al., J. Am. Chem. Soc., 126, 6872 – 6873 (2004).
V. L. Novikov, O. P. Shestak, A. V. Kamernitskii, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1390 – 1393 (1980).
O. P. Shestak, V. L. Novikov, and S. I. Stekhova, Khim.-farm. Zh., 32(11), 21 – 23 (1998).
O. P. Shestak and V. L. Novikov, in: Abstracts of Papers of the IXth All-Union Symposium on Targeted Drug Discovery [in Russian], Riga, Latvia (1991), p. 71.
V. L. Novikov and O. P. Shestak, in: Abstracts of Papers of the VIIth All-Union Conference on the Chemistry of Dicarbonyl Compounds [in Russian], Riga, Latvia (1991), p. 143.
O. P. Shestak and V. L. Novikov, in: Abstracts of Papers of the Vth All-Union Conference on the Chemistry of N-Containing Heterocyclic Compounds [in Russian], Chernogolovka (1991), p. 281.
O. P. Shestak, V. L. Novikov, S. I. Stekhova, et al., Khim.-farm. Zh., 33(1), 18 – 21 (1999).
O. P. Shestak, V. L. Novikov, N. G. Prokof'eva, et al., in: Abstracts of Papers of the All-Russian Conference “New Drugs: Progress and Prospects” [in Russian], Ufa (2005), pp. 72 – 75.
O. P. Shestak, V. L. Novikov, E. A. Martyyas, et al., Khim.farm. Zh., 43(9), 16 – 19 (2009).
O. P. Shestak, V. L. Novikov, N. G. Prokof’eva, et al., Khim.farm. Zh., 33(12),5–8 (1999).
S. Arpadjan and D. Stojanova, Fresenius Z. Anal. Chem., 302, 206 (1980).
Z. P. Belousova, V. A. Osyanin, and N. A. Klenova, Khim.farm. Zh., 41(12), 16 – 17 (2007).
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The work was supported financially by the FEB RAS, Grant No. 09-III-A-05-149.
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 45, No. 8, pp.8–11, August, 2011.
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Shestak, O.P., Novikov, V.L., Martyyas, E.A. et al. Synthesis and hemolytic activity of cyclopentane and hydrindane 2-acetyl-1,3-diones. Pharm Chem J 45, 454–457 (2011). https://doi.org/10.1007/s11094-011-0653-4
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DOI: https://doi.org/10.1007/s11094-011-0653-4