Book of Abstracts - Ruhr-Universität Bochum

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P-77 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum Water Enables Direct Palladium-Catalyzed C-allylation of Cyclic 1,3-Diones with Allylic Alcohols without Activators Shyh-Chyun Yang *a and Yi-Jen Shue a a Kaohsiung Medical University, School of Pharmacy, 100 Shih-Chuan 1st Road, 807, Kaohsiung, Taiwan. E-mail: scyang@kmu.edu.tw The palladium-catalyzed allylation is a powerful tool for C–C, C–N, and C–O bond formation, which has been widely applied to organic chemistry. We have recently disclosed a new catalytic system for palladium/carboxylic acid–catalyzed allylation with allylic alcohols in water as a suspension medium. 1 Organic reactions in water have recently attracted much attention, because water is a safe and economical substitute for conventional organic solvent. Herein, we report that palladium-catalyzed ally-OH bond cleavage in the absence of activating agents. Allylation of cyclic 1,3-diones worked well with aromatic allylic alcohols in water and gave generally good to high yields. This is a simple and efficient route for C–C bond formation. References O O R Pd /P-ligand, H 2O OH R 135 R R O O + O O 1. (a) S.-C. Yang, Y.-C. Hsu, K.-H. Gan. Tetrahedron 2006, 62, 3949-3958. (b) K.-H. Gan, C.-J. Jhong, S.-C. Yang, Tetrahedron 2008, 64, 1204-1212.
P-78 ISBOMC `10 5.7 – 9.7. 2010 Ruhr-Universität Bochum In Vitro Interactions of Rhenium(III) Compounds with Phospholipids and Nucleic Bases Derivatives a Dina Y. Yegorova, b Nataliia I. Shtemenko, a Alexander V. Shtemenko a Department of Inorganic Chemistry, Ukrainian State Chemical Technological University, Gagarin Ave. 8, Dnipropetrovs’k 49005, Ukraine. E-mail: shtemenko@ukr.net, b Department of Biophysics and Biochemistry, Dnipropetrovs’k National University, 72 Gagarin avenue, Dnipropetrovs’k 49010, Ukraine In our previous investigations it was shown that rhenium(III) complexes had antitumor, antihemolytic and red blood cells stabilizing properties. 1 The important component of the integral biological activity of any substance is its ability to cross the cell membrane and to react with nuclear bases. Investigations of the interaction between rhenium(III) cluster complexes and phospholipids as one of the main components of a cell membrane and nuclear bases is of great importance as may help to understand the mechanism of their action and to find further synthetic directions. In this work the experiments were accomplished with cluster rhenium(III) compounds with common formulas: [Bu4N]2×[Re2Cl8], cis-[Re2(CH3COO)2Cl4]×2H2O, trans-Re2(C2H5COO)2Cl4 , Re2(RCOO)3Cl3, Re2(RCOO)4Cl2, where R - CH3, C2H5, i-C3H7, C10H15; with phospholipids: phosphatidylcholine, phosphatidylserine, phosphatidylethanolamine and nuclear bases derivatives: 9methyladenin and 9-methylguanin. The electronic absorbtion spectra of mixtures of the substances were studied. According to the obtained spectra the strongest interaction was found with phosphatidylholine among other main phospholipids of cells membrane. It was shown that the mechanism of interaction depended on the structural type of cluster rhenium(III) complexes. In the case of tetra-μ-carboxylates bridged equatorial carboxylic groups were replaced by phosphate groups of phosphatidylholine with following formation of monodentate derivatives. During interaction of phosphatidylholine with cistetrachlorodi-μ-carboxylates of dirhenium(III) replacement of terminal chlorides by phosphatidylholine ligands with formation of monodentate derivatives with the change of the previous structural type was shown. The same interactions were shown to be realized during formation of nanoliposomes of cluster rhenium(III) compounds and phosphatidylholine. Hydrolytic process of the complex rhenium(III) compounds was shown to take place in water solutions, that’s why nanoliposomal forms of rhenium(III) complex compounds were obtained from phosphatidylholine to prolong their therapeutic effect. It was shown that the coordination of phosphate groups of phosphatidylholine to the cluster centre (unit) of Re2 6+ provided prevention of hydrolytic process and increased the stability of these compounds. Bidentate coordination of the 9 MeA to equatorial position of the cluster Re2 6+ centre through N1/N6 atoms of the nucleic base heterocidic ring was shown. Another type of coordination was shown for Guanine derivative: 9MeG coordinated by monodentate mode to axial position of the Re2 6+ centre only through N1 atom of the heterocidic ring. The mechanism of interaction between nucleic bases and rhenium(III) compounds was different in comparison with the same for platinides that explained the effectiveness of the Rhenium – Platinum antitumor system in the earlier experiments in vivo. References 1. (a) N. Shtemenko, P. Collery, A. Shtemenko, Anticancer Res. 2007, 27, 2487-2492. (b) A. Shtemenko, P. Collery, N. Shtemenko, K. Domasevitch, E. Zabitskaya, A. Golichenko, Dalton Trans. 2009, 5132-5136. 136
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Page 145 and 146: Sergey Abramkin Universität Wien,
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