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(E)-2-Benzylidenebenzocyclanones: part XIII—(E)/(Z)-Isomerization of some cyclic chalcone analogues. Effect of ring size on lipophilicity of geometric isomers

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Abstract

Optimized isocratic reverse phase high-performance liquid chromatography (RP-HPLC) method was developed for separation of the respective (E) and (Z) isomers of the cyclic chalcone analogues (E)-2-(4′-X-benzylidene)-1-indanones, -tetralones, and -benzosuberones. The method has been applied to monitor progress of the light-induced (E)/(Z) isomerization process in the three series. Data indicate formation of equilibrium mixtures of the respective geometric isomers. Comparison of the HPLC retention factors of the respective geometric isomers showed the (Z) isomers less lipophilic in the benzosuberone and the tetralone but more lipophilic in the indanone series. Data provide experimental evidence of opposite effect of ring size and geometric isomerism on lipophilicity of conformationally restricted (cyclic) analogues of chalcone, an open chain pharmacophore.

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References

  1. Veliká B, Tomecková V, Fodor K, Kron I, Perjési P (2015) Spectr Anal Rev 3:1

    Article  Google Scholar 

  2. Perjési P, Nusser T, Tarczay Gy, Sohár P (1999) J Mol Struct 479:13

    Article  Google Scholar 

  3. Dimmock JR, Kandepu NM, Nazarali AJ, Kowalchuk TP, Motaganahalli N, Quail JW, Mykytiuk PA, Audette GF, Prasad L, Perjési P, Allen TM, Santos CL, Szydlowski J, De Clercq E, Balzarini J (1999) J Med Chem 42:1358

    Article  CAS  Google Scholar 

  4. Dimmock JR, Zello GA, Oloo EO, Quail JW, Kraatz H-B, Perjési P, Aradi F, Takács-Novák K, Allen TM, Santos CL, Balzarini J, De Clerq E, Stables JP (2002) J Med Chem 45:3103

    Article  CAS  Google Scholar 

  5. Rozmer Zs, Berki T, Perjési P (2006) Toxicol In Vitro 20:1354

    Article  CAS  Google Scholar 

  6. Rozmer Zs, Berki T, Maász G, Perjési P (2014) Toxicol In Vitro 28:1359

    Article  CAS  Google Scholar 

  7. Dimmock JR, Elias DW, Beazely MA, Kandepu NM (1999) Curr Med Chem 6:1125

    CAS  Google Scholar 

  8. Ni L, Meng CQ, Sikorski JA (2004) Expert Opin Ther Pat 14:1669

    Article  CAS  Google Scholar 

  9. Go ML, Wu X, Liu XL (2005) Curr Med Chem 12:483

    Article  CAS  Google Scholar 

  10. Fodor K, Tomeckova V, Kőszegi T, Kron I, Perjési P (2011) Monatsh Chem 142:463

    Article  CAS  Google Scholar 

  11. Tomeckova V, Stefanisinova VM, Velika B, Fodor K, Perjési P, Stupak M, Guzy J, Tóth S Jr, Pekarova T (2013) Spectr Anal Rev 1:1

    Article  Google Scholar 

  12. Dhar DN (1981) The chemistry of chalcones and related compounds. John Wiley and Sons, New York, p 168

    Google Scholar 

  13. Schuster DI (1989) The photochemistry of enones. In: Patai S, Rappoport Z (eds) The chemistry of enones. John Wiley and Sons, Chichester, p 623

    Google Scholar 

  14. Miquel JF (1961) Bull Soc Chim Fr 1369

  15. Iwata S, Nishino T, Inoue H, Nagata N, Satomi Y, Nishino H, Shibata S (1977) Biol Pharm Bull 20:1266

    Article  Google Scholar 

  16. Schleuder M, Am Ali F, Otto HH (2003) Pharmazie 58:308

    CAS  Google Scholar 

  17. Imbach JL, Pohland AE, Weiler ED, Cromwell NH (1967) Tetrahedron 23:3931

    Article  CAS  Google Scholar 

  18. Kevill DN, Weiler ED, Cromwell NH (1964) J Org Chem 29:1276

    Article  CAS  Google Scholar 

  19. Azzolina O, Desimoni G, Di Toro V, Gishlandi V, Tacconi G (1975) Gazz Chim Ital 105:971

    CAS  Google Scholar 

  20. Pliska V (1996) The role of lipophilicity in biological response to drugs and endogenous ligands. In: Pliska V, Testa B, van de Waterbeemd H (eds) Lipophilicity in drug action and toxicology. VCH Publishers, Weinheim, p 263

    Chapter  Google Scholar 

  21. Perjési P, Takács M, Ősz E, Pintér Z, Vámos J, Takács-Novák K (2005) J Chromatogr Sci 43:289

    Article  Google Scholar 

  22. Giaginis C, Tsantili-Kakoulidou JA (2008) Liq Chrom Rel Technol 31:79

    Article  CAS  Google Scholar 

  23. Dugave C, Demange L (2003) Chem Rev 103:2475

    Article  CAS  Google Scholar 

  24. Gelsomini N, Mazza LJ, Guarna A (1974) J Chromatogr 101:182

    Article  CAS  Google Scholar 

  25. Shin DM, Song DM, Jung KH, Moon JH (2001) J Photosci 8:9

    Google Scholar 

  26. Tomeckova V, Poskrobova M, Stefanisinova M, Perjési P (2009) Spectrochim Acta Part A Mol Biomol Spectr 74:1242

    Article  Google Scholar 

  27. Tehfe MA, Dumur F, Xiao P, Delgove M, Graff B, Fouassier J-P, Gigmes D, Lalevée J (2014) Polym Chem 5:382

    Article  CAS  Google Scholar 

  28. Stratonnikov AA, Meerovich GA, Loschenov VB (2000) Proc SPIE 3909:81

    Article  CAS  Google Scholar 

  29. Walczak B, Lafosse M, Chrétien JR, Dreux M, Morin-Allory L (1986) J Chrom 369:27

    Article  CAS  Google Scholar 

  30. Testa B, Carrupt PA, Gaillard P, Tsaiin R-S (1996) Intramolecular interactions encoded in lipophilicity: Their nature and significance. In: Pliska V, Testa B, van de Waterbeemd H (eds) Lipophilicity in drug action and toxicology. VCH Publishers, Weinheim, p 49

    Chapter  Google Scholar 

  31. Perjési P, Perjessy A, Kolehmainen E, Ősz E, Samalikova M, Virtanen E (2004) J Mol Struct 697:41

    Article  Google Scholar 

  32. Perjési P, Linnanto J, Kolehmainen E, Ősz E, Virtanen E (2005) J Mol Struct 740:81

    Article  Google Scholar 

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Acknowledgments

The author expresses his special thanks to Szilárd Molnár (South-Transdanubian Environmental Protection Inspectorate, Pécs-Cserkút, Hungary) for his participation in recording the GC–MS spectra. This study was supported by the University of Pécs Faculty of Medicine Research Fund (PTE AOK-KA-2013/20).

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  1. Institute of Pharmaceutical Chemistry, University of Pécs, Pécs, Hungary

    Pál Perjési

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  1. Pál Perjési
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Correspondence to Pál Perjési.

Additional information

For part XII of this series, see Ref. [1].

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Perjési, P. (E)-2-Benzylidenebenzocyclanones: part XIII—(E)/(Z)-Isomerization of some cyclic chalcone analogues. Effect of ring size on lipophilicity of geometric isomers. Monatsh Chem 146, 1275–1281 (2015). https://doi.org/10.1007/s00706-015-1463-2

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