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2012 | 10 | 5 | 1500-1505
Tytuł artykułu

Comparison of structure, logP and P388 cytotoxicity of some phenyl and ferrocenyl cyclic chalcone analogues. Application of RP-TLC for logP determination of the ferrocenyl analogues

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Cyclic chalcone analogues (2–5) and their ferrocenyl counterparts (6–10) were synthesized and their logP and P388 cyctotoxity were investigated. The structures of the newly synthesized compounds were confirmed by IR 1H and 13NMR spectroscopy. Comparison of conjugation and stereochemistry of the respective derivatives showed similar characteristics compared to ones with some higher degree of conjugation in the ferrocenyl series. Comparison of logP of the ferrocenyl derivatives determined by a validated RP-TLC method showed the ferrocenyl derivatives to have higher logP TLC. The results demonstrate that the differences in three dimensional shape, conjugation and lipophilicity do not have strong influence on the P388 cytotoxicity of the investigated phenyl (1−5) and ferrocenyl (6−10) enones. [...]
Wydawca

Czasopismo
Rocznik
Tom
10
Numer
5
Strony
1500-1505
Opis fizyczny
Daty
wydano
2012-10-01
online
2012-07-21
Twórcy
  • Institute of Pharmaceutical Chemistry, Semmelweis University, Budapest, 1092, Hungary
  • Institute of Pharmaceutical Chemistry, University of Pécs, Pécs, 7634, Hungary
autor
  • Department of Chemistry, Eötvös Lóránd University (ELTE), and Protein Modelling Group ELTE-HAS, Budapest, 1117, Hungary, sohar@chem.elte.hu
  • Department of Chemistry, California State University Hayward, Hayward, CA, 94542, USA
  • Department of Pharmacology, University of Alberta, Edmonton, AB, T6G 2H7, Canada
Bibliografia
  • [1] I. Kron, Z. Pudychová-Chovanová, B. Veliká, J. Guzy, P. Perjési, Monatsh. Chem. 143, 13 (2012) http://dx.doi.org/10.1007/s00706-011-0633-0[Crossref]
  • [2] V. Zsoldos-Mády, O. Ozohanics, A. Csámpai, V. Kudar, D. Frigyes, P. Sohár, J. Organomet. Chem. 694, 4185 (2009) http://dx.doi.org/10.1016/j.jorganchem.2009.09.007[Crossref]
  • [3] J.B. Harborne, In: V. Cody, E. Middleton Jr., E. Harborne (Eds.), Plant flavonoids in Biology and Medicine: Biochemical, pharmacological and structure-activity relationships (Alan R. Liss. Inc., New York, 1986) 15
  • [4] J.R. Dimmock, D.W. Elias, M.A. Beazely, N.M. Kandepu, Curr. Med. Chem. 6, 1125 (1999)
  • [5] M.L. Go, X. Wu, X.L. Liu, Curr. Med. Chem. 12, 483 (2005) http://dx.doi.org/10.2174/0929867053363153[Crossref]
  • [6] J.R. Dimmock, N.M. Kandepu, A.J. Nazarali, T.P. Kowalchuk, N. Motaganahalli, J.W. Quail, P. Mykytiuk, G.F. Audette, L. Prasad, P. Perjési, T.M. Allen, C.L. Santos, J. Szydlowski, E. De Clercq, J. Balzarini, J. Med. Chem. 42, 1358 (1999) http://dx.doi.org/10.1021/jm9806695[Crossref]
  • [7] J.R. Dimmock, G.A. Zello, E.O. Oloo, J.W. Quail, H-B. Kraatz, P. Perjési, K. Takács-Novák, F. Aradi, T.M. Allen, C.L. Santos, J. Balzarini, E. DeClerq, J.P. Stables, J. Med. Chem. 45, 3103 (2002) http://dx.doi.org/10.1021/jm010559p[Crossref]
  • [8] P. Perjési, U. Das, E. De Clercq, J. Balzarini, M. Kawase, H. Sakagami, J.P. Stables, T. Loránd, Zs. Rozmer, J.R. Dimmock, Eur. J. Med. Chem. 43, 839 (2008) http://dx.doi.org/10.1016/j.ejmech.2007.06.017[Crossref]
  • [9] A. Valkonen, K. Laihia, E. Kolehmainen, R. Kauppinen, P. Perjési, Struct. Chem. 23, 209 (2012) http://dx.doi.org/10.1007/s11224-011-9860-6[Crossref]
  • [10] P. Perjési, T. Nusser, Gy. Tarczay, P. Sohár, J. Mol. Struct. 479, 13 (1999) http://dx.doi.org/10.1016/S0022-2860(98)00805-9[Crossref]
  • [11] P. Perjési, Zs. Bayer, I. Ember, Anticancer Res. 20, 475 (2000)
  • [12] K. Monostory, V. Tamási, L. Vereczkey, P. Perjési, Toxicology 184, 203 (2003) http://dx.doi.org/10.1016/S0300-483X(02)00578-4[Crossref]
  • [13] Zs. Rozmer, T. Berki, P. Perjési, Toxicol. in Vitro 20, 1354 (2006) http://dx.doi.org/10.1016/j.tiv.2006.05.006[Crossref]
  • [14] P. Perjési, J. Kubalkova, Z. Chovanova, M. Marekova, Zs. Rozmer, K. Fodor, Z. Chavkova, V. Tomeckova, J. Guzy, Pharmazie 63, 899 (2008)
  • [15] C. Hansch, A. Leo, Substituent Constants for Correlation Analysis in Chemistry and Biology (John Wiley and Sons, New York, 1979)
  • [16] W.Y. Liu, T. Xie, Y.M. Liang, W.M. Liu, Y.X. Ma, J. Organometallic Chem. 627, 93 (2001) http://dx.doi.org/10.1016/S0022-328X(01)00717-3[Crossref]
  • [17] C. Biot, Curr. Med. Chem. - Anti-Infective Agents 3, 135 (2004) http://dx.doi.org/10.2174/1568012043354008[Crossref]
  • [18] S. Top, A. Vessières, C. Cabestaing, et al. J. Organometallic Chem. 500, 637 (2001)
  • [19] R. Kovjazin, T. Eldar, M. Patya, A. Vanichkin, H.M. Lander, A. Novogrodsky, FASEB J. 17, 467 (2003)
  • [20] E. Hillard, A. Vessieres, F. Le Bideau, D. Plazuk, D. Spera, M. Huche, G. Jaouen, Chem. Med. Chem. 1, 551 (2006)
  • [21] S.V. Lindeman, R.E. Bozak, R.J. Hicks, S. Husebye, Acta Chem. Scand. 51, 966 (1997) http://dx.doi.org/10.3891/acta.chem.scand.51-0966[Crossref]
  • [22] X. Wu, E. R.T. Tiekink, I. Kostetski, N. Kocherginsky, A. L.C. Tan, S. B. Khoo, P. Wilairat, M.-L. Go, Eur. J. Pharm. Sci. 27, 175 (2006) http://dx.doi.org/10.1016/j.ejps.2005.09.007[Crossref]
  • [23] M.S. Tute, Lipophilicity: A History. In: R. Mannhold, H. Kubiny, H. Timmerman (Eds.) Methods and Principles in Medicinal Chemistry, Vol. 4 - V. Pliska, B. Testa, H. van de Waterbeemd, Lipophilicity in Drug Action and Toxicology (VHC Publishers, Inc., Weinheim, FRG, 1996) 7–26
  • [24] K. Takács-Novák, P. Perjési, J. Vámos, JPC-J. Planar Chrom. 14, 42 (2001)
  • [25] P. Perjési, M. Takács, E. Ősz, Z. Pintér, J. Vámos, K. Takács-Novák, J. Chromatogr. Sci. 43, 289 (2005) [Crossref]
  • [26] Zs. Rozmer. P. Perjési, K. Takács-Novák, J. Planar Chrom. - Modern TLC 19, 124 (2006) http://dx.doi.org/10.1556/JPC.19.2006.2.7[Crossref]
  • [27] M.H. Abraham, N. Benjelloun-Dakhama, J.M.R. Gola, W.E. Jr. Acree, W.S. Cain, J.E. Cometto-Muniz, New J. Chem. 24, 825 (2000) http://dx.doi.org/10.1039/b004291i[Crossref]
  • [28] P. Sohár, P. Perjési, K.W. Törnroos, S. Husebye, A. Vértes, Gy. Vankó, R.E. Bozak, J. Mol. Struct. 524, 297 (2000) http://dx.doi.org/10.1016/S0022-2860(00)00380-X[Crossref]
  • [29] O.A. Phillips, L.A. Nelson, E.E. Knaus, T.M. Allen, R. Fathi-Afshar, Drug Des. Deliv. 4, 121 (1989)
  • [30] P. Perjési, A. Perjessy, E. Kolehmainen, E. Ősz, M. Samalikova, E. Virtanen, J. Mol Struct. 697, 41 (2004) http://dx.doi.org/10.1016/j.molstruc.2004.02.006[Crossref]
  • [31] P. Perjési, J. Linnanto, E. Kolehmainen, E. Ősz, E. Virtanen, J. Mol. Struct. 740, 81 (2005) http://dx.doi.org/10.1016/j.molstruc.2004.10.013[Crossref]
  • [32] A. Hoser, Z. Kaluski, H. Maluszynska, V.D. Orlov, Acta Crystallogr. B36, 1256 (1980) [Crossref]
  • [33] Z. Kaluski, E. Skrzypczak-Jankun, V.D. Orlov, I.A. Borovoi, Bull. Acad. Pol. Sci., Ser. Sci. Chim. 26, 869 (1978)
  • [34] P. Sohár, A. Csámpai, P. Perjési, Arkivok (V),114 (2003)
  • [35] A. Katrusiak, M. Ratajczak-Sitarz, Z. Kaluski, V.D. Orlov, Acta Crystallogr. C43, 103 (1987)
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-012-0088-0
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