Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Open Chemistry

formerly Central European Journal of Chemistry


IMPACT FACTOR 2017: 1.425
5-year IMPACT FACTOR: 1.511

CiteScore 2017: 1.45

SCImago Journal Rank (SJR) 2017: 0.349
Source Normalized Impact per Paper (SNIP) 2017: 0.812

ICV 2017: 165.27

Open Access
Online
ISSN
2391-5420
See all formats and pricing
More options …
Volume 7, Issue 3

Issues

Volume 13 (2015)

RP-HPLC determination of lipophilicity in series of quinoline derivatives

Robert Musiol / Josef Jampilek
  • Zentiva a.s., 10237, Prague 10, Czech Republic
  • Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, 61242, Brno, Czech Republic
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Barbara Podeszwa / Jacek Finster / Dominik Tabak / Jiri Dohnal
  • Zentiva a.s., 10237, Prague 10, Czech Republic
  • Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, 61242, Brno, Czech Republic
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Jaroslaw Polanski
Published Online: 2009-06-21 | DOI: https://doi.org/10.2478/s11532-009-0059-2

Abstract

In the present paper we describe results on the synthesis and lipophilicity determination of a series of biologically active compounds based on their heterocyclic structure. For synthesis of styrylquinoline-based compounds we applied microwave irradiation and solid phase techniques. The correlation between RP-HPLC retention parameter log k (the logarithm of retention factor k) and log P data calculated in various ways is discussed, as well as, the relationships between the lipophilicity and the chemical structure of the studied compounds.

Keywords: Lipophilicity; RP-HPLC; Microwave synthesis; Quinoline derivatives

  • [1] H.J. Roth, H. Fenner Iarzneistoffe, 3rd edition (Deutscher Apotheker Verlag, Stuttgart, 2000) 51 Google Scholar

  • [2] C.R. Harris, A. Thorarensen, Curr. Med. Chem. 11, 2213 (2004) Google Scholar

  • [3] K. Andries, P. Verhasselt, J. Guillemont, H.W. Gohlmann, J.M. Neefs, H. Winkler, J. Van Gestel, P. Timmerman, M. Zhu, E. Lee, P. Williams, D. de Chaffoy, E. Huitric, S. Hoffner, E. Cambau, C. Truffot-Pernot, N. Lounis, V. Jarlier, Science 307, 223 (2005) http://dx.doi.org/10.1126/science.1106753CrossrefGoogle Scholar

  • [4] S. Vangapandu, M. Jain, R. Jain, S. Kaur, P.P. Singh, Bioorg. Med. Chem. 12, 2501 (2004) http://dx.doi.org/10.1016/j.bmc.2004.03.045CrossrefGoogle Scholar

  • [5] C. Sissi, M. Palumbo, Curr. Med. Chem. Anti-Canc. Agents 3, 439 (2003) http://dx.doi.org/10.2174/1568011033482279CrossrefGoogle Scholar

  • [6] E. Bossu, A.M. Agliano, N. Desideri, I. Sestili, R. Porra, M. Grandilone, M.G. Quaglia, J. Pharm. Biomed. Anal. 19, 53 (1999) http://dx.doi.org/10.1016/S0731-7085(98)00250-7CrossrefGoogle Scholar

  • [7] T.C. Ko, M.J. Hour, J.C. Lien, C.M. Teng, K.H. Lee, S.C. Kuo, L.J. Huang, Bioorg. Med. Chem. Lett. 11, 279 (2001) http://dx.doi.org/10.1016/S0960-894X(00)00652-1CrossrefGoogle Scholar

  • [8] J. Jampilek, M. Dolezal, J. Kunes, P. Vichova, D. Jun, I. Raich, R. O’Connor, M. Clynes, J. Pharm. Pharmacol. 56, 783 (2004) http://dx.doi.org/10.1211/0022357023484CrossrefGoogle Scholar

  • [9] J. Jampilek, M. Dolezal, J. Kunes, P. Vichova, D. Jun, I. Raich, R. O’Connor, M. Clynes, Curr. Org. Chem. 8, 1235 (2004) http://dx.doi.org/10.2174/1385272043370041CrossrefGoogle Scholar

  • [10] J. Jampilek, M. Dolezal, V. Opletalova, J. Hartl, Curr. Med. Chem. 13, 117 (2006) http://dx.doi.org/10.2174/092986706775197935CrossrefGoogle Scholar

  • [11] J.L. Marco, C.M. Carmo, Mini Rev. Med. Chem. 3, 518 (2003) http://dx.doi.org/10.2174/1389557033487908CrossrefGoogle Scholar

  • [12] K. Mekouar, J.-F. Mouscadet, D. Desmaele, F. Subra, H. Leh, D. Savoure, C. Auclair, J. d’Angelo, J. Med. Chem. 41, 2846 (1998) http://dx.doi.org/10.1021/jm980043eCrossrefGoogle Scholar

  • [13] J. Polanski, F. Zouhiri, L. Jeanson, D. Desmaele, J. d’Angelo, J-F. Mouscadet, R. Gieleciak, J. Gasteiger, M. Le Bret, J. Med. Chem. 45, 4647 (2002) http://dx.doi.org/10.1021/jm020845gCrossrefGoogle Scholar

  • [14] J. Polanski, H. Niedbala, R. Musiol, D. Tabak, B. Podeszwa, R. Gieleciak, A. Bak, A. Palka, T. Magdziarz, Acta Polonia Pharm. Drug Res. 61, 3 (2004) Google Scholar

  • [15] Y. Pommier, A.A. Johnson, C. Marchand, Nat. Rev. Drug. Discov. 4, 236 (2005) http://dx.doi.org/10.1038/nrd1660CrossrefGoogle Scholar

  • [16] F. Zouhiri, D. Danet, C. Bernard, M. Normand-Bayle, J. F. Mouscadet, H. Leh, C.M. Thomas, G. Mbemba, J. d’Angelo, D. Desmaele, Tetrahedron Lett. 46, 2201 (2005) http://dx.doi.org/10.1016/j.tetlet.2005.02.033CrossrefGoogle Scholar

  • [17] R. Musiol, J. Jampilek, V. Buchta, L. Silva, H. Niedbala, B. Podeszwa, A. Palka, K.A. Majerz-Maniecka, B. Oleksyn, J. Polanski, Bioorg. Med. Chem. 14, 3592 (2006) http://dx.doi.org/10.1016/j.bmc.2006.01.016CrossrefGoogle Scholar

  • [18] J. Jampilek, M. Dolezal, J. Kunes, V. Buchta, K. Kralova, Med. Chem. 1, 591 (2005) http://dx.doi.org/10.2174/157340605774598108CrossrefGoogle Scholar

  • [19] R. Musiol, J. Jampilek, K. Kralova, D.R. Richardson, D. Kalinowski, B. Podeszwa, J. Finster, H. Niedbala, A. Palka, J. Polanski, Bioorg. Med. Chem. 15, 1280 (2007) http://dx.doi.org/10.1016/j.bmc.2006.11.020CrossrefGoogle Scholar

  • [20] C.A. Lipinski, F. Lombardo, B.W. Dominy, P.J. Feeney, Adv. Drug. Delivery Rev. 23, 4 (1997) http://dx.doi.org/10.1016/S0169-409X(96)00423-1CrossrefGoogle Scholar

  • [21] A. Avdeef, Curr. Topics Med. Chem. 1, 277 (2001) http://dx.doi.org/10.2174/1568026013395100CrossrefGoogle Scholar

  • [22] V. Pliska, In V. Pliska, B. Testa, H. van der Waterbeemd (Eds.), Lipophilicity in Drug Action and Toxicology (Wiley-VCH, New York, 1996) 1 http://dx.doi.org/10.1002/9783527614998.ch1CrossrefGoogle Scholar

  • [23] S. Gocan, G. Cimpan, J. Comer, Adv. Chromatogr. 44, 79 (2006) Google Scholar

  • [24] K. Valko, C.M. Du, C. Bevan, D.P. Reynolds, M.H. Abraham, Curr. Med. Chem. 8, 1137 (2001) Google Scholar

  • [25] G. Cimpan, F. Irimie, S. Gocan, H.A. Claessens, J. Chromatogr. B 714, 247 (1998) http://dx.doi.org/10.1016/S0378-4347(98)00228-XCrossrefGoogle Scholar

  • [26] T. Hartmann, J. Schmitt, Drug Disc. Today Technol. 1, 431 (2004) http://dx.doi.org/10.1016/j.ddtec.2004.10.006CrossrefGoogle Scholar

  • [27] A. Nasal, D. Siluk, R. Kaliszan, Curr. Med. Chem. 10, 381 (2003) Google Scholar

  • [28] J.A. Rothwell, A.J. Day, M.R.A. Morgan, J. Agric. Food Chem. 53, 4355 (2005) http://dx.doi.org/10.1021/jf0483669CrossrefGoogle Scholar

  • [29] P. Ertl, P. Selzer, J. Muehlbacher, Drug Discov. Today 2, 201 (2004) http://dx.doi.org/10.1016/S1741-8364(04)02413-8CrossrefGoogle Scholar

  • [30] G.G. Nys, R.F. Rekker, Chim. Ther. 8, 521 (1973) Google Scholar

  • [31] G.G. Nys, R.F. Rekker, Chim. Ther. 9, 361 (1974) Google Scholar

  • [32] J. Cioslowski, A. Szarecka, D. Moncrieff, Molecular Physics 101, 1221 (2003) http://dx.doi.org/10.1080/0026897031000087630CrossrefGoogle Scholar

  • [33] B. Podeszwa, R. Musiol, D. Tabak, J. Finster, J. Polanski, H. Niedbala, A. Palka, Polish Patent Application P 380818 (2006) Google Scholar

  • [34] B. Podeszwa, H. Niedbala, J. Polanski, R. Musiol, D. Tabak, J. Finster, K. Serafin, M. Milczarek, J. Wietrzyk, S. Boryczka, W. Mol, J. Jampilek, J. Dohnal, D. Kalinowski, D.R. Richardson, Bioorg. Med. Chem. Let. 17, 6138 (2007) http://dx.doi.org/10.1016/j.bmcl.2007.09.040CrossrefGoogle Scholar

  • [35] K.A. Majerz-Maniecka, R. Musiol, W. Nitek, B.J. Oleksyn, J. Polanski, Bioorg. Med. Chem. Lett. 16, 1005 (2005) http://dx.doi.org/10.1016/j.bmcl.2005.10.083CrossrefGoogle Scholar

  • [36] R. Musiol, B. Podeszwa, J. Finster, H. Niedbala, J. Polanski, Monatsh. Chem. 137, 1211 (2006) http://dx.doi.org/10.1007/s00706-006-0513-1CrossrefGoogle Scholar

  • [37] R. Musiol, D. Tabak, H. Niedbala, B. Podeszwa, J. Jampilek, K. Kralova, J. Dohnal, J. Finster, A. Mencel, J. Polanski, Bioorg. Med. Chem. 16, 4490 (2008) http://dx.doi.org/10.1016/j.bmc.2008.02.065CrossrefGoogle Scholar

  • [38] J. Polanski, H. Niedbala, R. Musiol, B. Podeszwa, D. Tabak, A. Palka, A. Mencel, J.-F. Mouscadet, M. Le Bret, Letters in Drug Design and Discovery 4, 99 (2007) http://dx.doi.org/10.2174/157018007779422532CrossrefGoogle Scholar

  • [39] M. Yoshimoto, C. Hansch, J. Med. Chem. 19, 71 (1976) http://dx.doi.org/10.1021/jm00223a015CrossrefGoogle Scholar

  • [40] W.D. Warner, J.D. Musto, J.N. Sane, K.H. Kim, G.L. Grunewald, J. Med. Chem. 20, 92 (1977) http://dx.doi.org/10.1021/jm00211a019CrossrefGoogle Scholar

  • [41] G. Piraprez, M.F. Herent, S. Collin, Flavour Fragr. J. 13, 400 (1998) http://dx.doi.org/10.1002/(SICI)1099-1026(199811/12)13:6<400::AID-FFJ767>3.0.CO;2-XCrossrefGoogle Scholar

  • [42] K. Valko, J. Chromatogr. A 1037, 299 (2004) http://dx.doi.org/10.1016/j.chroma.2003.10.084CrossrefGoogle Scholar

  • [43] C. Yamagami, N. Takao, Chem. Express. 6, 113 (1991) Google Scholar

  • [44] C. Yamagami, K. Iwasaki, A. Ishikawa, Chem. Pharm. Bull. 45, 1953 (1997) Google Scholar

  • [45] C. Yamagami, K. Araki, K. Ohnishi, K. Hanasato, H. Inaba, M. Aono, A. Ohta, J. Pharm. Sci. 88, 1299 (1999) http://dx.doi.org/10.1021/js990112sCrossrefGoogle Scholar

  • [46] C. Yamagami, K. Kawase, K. Iwaki, Chem. Pharm. Bull. 50, 1578 (2002) http://dx.doi.org/10.1248/cpb.50.1578CrossrefGoogle Scholar

  • [47] M.H. Palmer, The Structure and Reactions of Heterocyclic Compounds (Edward Arnold Publisher Ltd., London, 1967) 105 Google Scholar

  • [48] J. Jampilek, J. Vinsova, J. Dohnal, In J.A. Seijas, M. P. Vázquez-Tato (Eds.), Electronic Conference on Synthetic Organic Chemistry, November 1–30, 2005 (MDPI, Basel, Switzerland, 2005) A008 Google Scholar

  • [49] J.D. Geerlings, C.A.G.O. Varma, J. Photochem. Photobiol. A. 129, 129 (1999) http://dx.doi.org/10.1016/S1010-6030(99)00190-2CrossrefGoogle Scholar

  • [50] M. Albrecht, K. Witt, R. Frohlich, O. Kataeva, Tetrahedron 58, 561 (2002) http://dx.doi.org/10.1016/S0040-4020(01)01168-1CrossrefGoogle Scholar

  • [51] A. Koll, A. Karpfen, P. Wolschann, J. Mol. Struct. 790, 55 (2006) http://dx.doi.org/10.1016/j.molstruc.2006.03.029CrossrefGoogle Scholar

About the article

Published Online: 2009-06-21

Published in Print: 2009-09-01


Citation Information: Open Chemistry, Volume 7, Issue 3, Pages 586–597, ISSN (Online) 2391-5420, DOI: https://doi.org/10.2478/s11532-009-0059-2.

Export Citation

© 2009 Versita Warsaw. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Maciej Serda, Anna Mrozek-Wilczkiewicz, Josef Jampilek, Matus Pesko, Katarina Kralova, Marcela Vejsova, Robert Musiol, Alicja Ratuszna, and Jaroslaw Polanski
Molecules, 2012, Volume 17, Number 11, Page 13483
[2]
Anna Hawrył, Edyta Kuśmierz, Mirosław Hawrył, Ryszard Świeboda, and Monika Wujec
Journal of Liquid Chromatography & Related Technologies, 2015, Volume 38, Number 4, Page 430
[3]
Wioleta Cieslik, Robert Musiol, Jacek E. Nycz, Josef Jampilek, Marcela Vejsova, Mariusz Wolff, Barbara Machura, and Jaroslaw Polanski
Bioorganic & Medicinal Chemistry, 2012, Volume 20, Number 24, Page 6960

Comments (0)

Please log in or register to comment.
Log in