Book of Abstracts - Ruhr-Universität Bochum

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P-21 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Antiproliferative Activity of Cationic and Neutral Heterobimetallic Ferrocene-(Vinyl)Ru(CO)Cl(P i Pr3)2 Complexes Konrad Kowalski, *a Ingo Ott, *b Rainer. F. Winter, c and Ronald Gust d a University of Łódź, Faculty of Chemistry, Department of Organic Chemistry, Tamka 12, 91-403 Łódź, Poland. b Technische Universität Braunschweig, Institute of Pharmaceutical Chemistry, Beethovenstraße 55, 38106 Braunschweig, Germany. c Universität der Regensburg, Institut für Anorganische Chemie, Universitätsstraße 31, D-93040 Regensburg, Germany. d Freie Universität Berlin, Institute of Pharmacy, Königin-Luise-Str. 2+4, 14195 Berlin, Germany. E-mail: kondor15@wp.pl Recently, some of us reported 1 on the mixed ferrocene ruthenium organometallic species 1 and 2 with the main focus on measuring the degree of electron delocalization in mixed-valent 2 and its medium dependence. In the bioorganometallic chemistry field the cytotoxic activity of some ferrocenium salts and the lack of activity of the corresponding ferrocenes is well known 2 . On the other hand the anticancer activity of mixed ferrocene/ruthenium complexes has been recently reported 3 . Considering these data, complexes 1 and 2 along with their monometallic counterparts 3-8 have been subjected toward biological studies 4 . Antiproliferative activity of 1-8 was carried out in HT-29 colon carcinoma and MCF-7 breast cancer cells. Both bimetallic derivatives 1 and 2 exhibited IC50 values between 4.8 μM and 16.8 μM. These values are within the range of common cytostatics such as cisplatin and 5fluorouracil investigated as control in the same assay. In addition our tests show higher antiproliferative activity of cationic 2 than of neutral 1. In order to rationalize this observation the cellular uptake of 1, 2 and 4 was determined by measurement of the ruthenium content of cells exposed to the complexes by atomic absorption spectroscopy. Unexpectedly, the cellular uptake of cationic 2 exceeded those of neutral 1 and were comparable to those exhibited by 4. This results suggest that 2 might be effectively transported across cellular lipid membranes by an active transporter system. Such a transporter systems are known to be crucial factors for cellular metal biodistribution. However, they haven’t been identified for any cationic ferrocenes yet. Fe P i Pr 3 Ru P i Pr 3 Cl CO Fe PiPr + 3 Ru P i Pr 3 Cl CO PF 6 - 1 2 3 79 Fe R R = -OCH 3 -F -CF 3 -N(CH 3) 2 -CHO Acknowledgements: KK is grateful to the Alexander von Humboldt-Stiftung for a research fellowship at the group of Prof. Dr. R. F. Winter, University of Regensburg References 1. K. Kowalski, M. Linseis, R. F. Winter, M. Zabel, S. Záliš, H. Kelm,; H-J. Krüger, B. Sarkar, W. Kaim, Organometallics 2009, 28, 4196. 2. G. Tabbi, G. Cassino, G. Cavigiolio, D. Colangelo, A. Ghiglia, I Viano, D. Osella, J. Med. Chem. 2002, 45, 5786. 3. M. Auzias, B. Therrien, G. Süss-Fink, P. Stepnicka, W.H. Ang, P. J. Dyson, Inorg. Chem. 2008, 47, 578. 4. I. Ott, K. Kowalski, R. Gust, J. Maurer, P. Mücke, R.F. Winter, Bioorg. Med. Chem. Lett. 2010, 20, 866-869. P i Pr 3 Ru P i Pr 3 4 5 6 7 8 Cl CO
P-22 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Green Chemistry in the Production of Ferrocene Derivatives Using Recyclable Solid Heteropolyacids as Catalysis Jorge Jios, a Gustavo Romanelli, b and Nils Metzler-Nolte *c a Laseisic (CIC-CONICET-UNLP), Departamento de Química, Facultad de Ciencias Exactas, UNLP. Camino Centenario e/505 y 508, CP1897, Gonnet, Argentina. b Centro de Investigación y Desarrollo en Ciencias Aplicadas “Dr. J. J. Ronco” (CINDECA), Departamento de Química, Facultad de Ciencias Exactas, UNLP-CONICET. Calle 47 Nº 257, B1900AJK La Plata, Argentina. c Lehrstuhl für Anorganische Chemie I, Bioanorganische Chemie, Fakultät für Chemie und Biochemie, Ruhr- Universität Bochum, Universitätsstrasse150, D-44801 Bochum, Germany. E-mail: jljios@quimica.unlp.edu.ar Dihydropyrimidinone are known to exhibit a wide range of biological activities such as antiviral, antitumour, antibacterial, and anti-inflammatory properties. 1 Several reagents/methods have been reported for their preparation under milder and more efficient procedures such as Amberlyst-15, Nafion-H, KSF clay with dry acetic acid under microwave irradiation, ionic liquids, cerric ammonium nitrate under ultrasonication, Lewis acids with transition metals, lanthanides, and indium chloride. 2 In this work we present an improved procedure for the obtention of dihydropyrimidinones bearing ferrocene in a three component one-pot condensation reaction using heteropolyacid catalysts (Figure 1). R Fe +2 + O O C O H R´ NH 2CONH 2 Superacid Catalyst The results are discussed in terms of the catalyst used, their selectivity and the reaction conversion degree. The aim of this work is investigate a convenient synthesis for the production of new metallocene carrying heterocyclic compounds with biological activities. The spectral data are discussed in detail. References 1. C. O. Kappe, Tetrahedron 1993, 49, 6937-6963, and references cited therein. 2. (a) F. Bigi, S. Carloni, B. Frullanti, R. Maggi, G. Sartori, Tetrahedron Lett. 1999, 40, 3465-3468. (b) J. Peng, Y. Deng, Tetrahedron Lett. 2001, 42, 5917-5919. (c) J. S. Yadav, B. V. S. Reddy, K. B. Reddy, K. S. Raj, A. R. J. Prasad, Chem. Soc. Perkin Trans. 1 2001, 1939-1941. (d) E. H. Hu, D. R. Sidler, U. H. Dolling, J. Org. Chem. 1998, 63, 3454-3457. (e) Y. Ma, C. Qian, L. Wang, M. Yang, J. Org. Chem. 2000, 65, 3864-3868. (f) J. Lu, Y. Bai, Z. Wang, B. Yang, H. Ma, Tetrahedron Lett. 2000, 41, 9075-9078. (g) B. C. Rannu, A. Hajra, U. Jana, J. Org. Chem. 2000, 65, 6270-6272. (h) H. N. Karade, M. Sathe, M. P. Kaushik. Molecules 2007, 12, 1341-1351. 80 R' O R Fe +2 N H NH O
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ISBOMC ‘10 5th International Symp
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Foreword ISBOMC `10 5.7 - 9.7. 2010
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General information ISBOMC `10 5.7
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Monday, July 5 th 2010 16:00 to 18:
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Sergey Abramkin Universität Wien,
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Tensim Dallagi ENSCP, France t.dall
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Prof. Dr. Toshikazu Hirao Osaka Uni
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Obiora Augustine Orakwue Hyqid Nige
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