Synthesis of New C- and N-Glycopyranosyl Azoles and Their Half-Sandwich Ru(II) Complexes

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Synthesis of New C- and N-Glycopyranosyl Azoles and Their Half-Sandwich Ru(II) Complexes

László Somsák 1 , István Kacsir 1 , Éva Bokor 1 , Péter Buglyó 2 , Attila Bényei 3 , Tibor Docsa 4 , Ádám Sipos 4

1 Department Of Organic Chemistry, University Of Debrecen, Debrecen, Hungary, 2 Department of Inorganic and Analytical Chemistry, University of Debrecen, Debrecen, Hungary, 3 Department of Physical Chemistry, University of Debrecen, Debrecen, Hungary, 4 Department of Medicinal Chemistry, Faculty of Medicine, University of Debrecen, Debrecen, Hungary

Cancer is among the most prevalent diseases worldwide. The patients suffering from tumors can be treated, among others, by platinum-based chemotherapeutic agents (cisplatin, oxaliplatin). Since these drugs have numerous side-effects, new platinum metal complexes (Ru, Os, Rh, Ir) as potential anticancer agents have also been investigated. In this context, the half-sandwich type complexes of Ru(II) have emerged as a promising compound class. [1,2]

Tumor cells are characterized by significantly increased glucose uptake compared to normal cells. Based on this fact, the application of carbohydrate derivatives incorporated into metal complexes is considered, which ‒ by means of their sugar moiety ‒ may have influence on the carbohydrate metabolism of the cancer cells e.g. as ligands of glucose transporters [2] or as inhibitors of the glycogen phosphorylase [3] enzyme.

Recently, some cyclopentadienyl-ruthenium(II) complexes with C-glycosylated N-heterocylic ligands (heterocycles: 1,3,4-oxadiazole, tetrazole) have been shown to display remarkable cytotoxic activity. [4,5]

Based on these pleriminaries, preparation of new five-membered glycopyranosyl heterocycles and their complexation with [(p-cym)Ru(II)Cl2]2 were planned. C- and N-Glycopyranosyl and C-glucosaminyl azoles (1,3,4-oxadiazoles, 1,2,3-triazoles, thiazoles, imidazoles) have been synthesized, which can coordinate as bidentate ligands to Ru(II), on the other hand they have the potential to inhibit the glycogen phosphorylase enzyme.

In the presentation synthetic details of the new glycosyl heterocycles, their enzyme kinetic evaluation and the results of their complexation reactions will be summarized.

Melchart, M.; Sadler, P. J. Ruthenium Arene Anticancer Complexes In Bioorganometallics, G. Jaouen, Ed. Wiley-VCH Verlag GmbH & Co. KGaA, 2006 39-64.

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Fernandes, A. C.;, Florindo, P.; Pereira, D. M.; Borralho, P. M.; Rodrigues, C. M. P.; Piedade, M. F. M. J. Med. Chem., 2015, 58, 4339−4347.

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