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Design and Synthesis of Crown Ether Thiosemicarbazones
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1  University of Santiago de Compostela, Department of Inorganic Chemistry


Thiosemicarbazones are well known compounds that show antitumoral and antibacterial proprieties[1] ; while crown ether moiety acts as ion sensor to entrap cations size-selectively from the environment, implied in the production of sensors, membrane ion transport or potential anti-cancerous species, among others[2]. The combination of both functions into the same molecule should increase their unique applications.

Herein we report on the synthesis of a molecule that combines both functions. The main aspect is that the study has being performed beginning with the design of the compound using DFT calculations, with the package of programs g09[3], after which follows the final synthesis and characterization using 1H NMR, IR and crystallographic analysis.


We wish to thank the financial support received from the Xunta de Galica (Galicia, Spain) under the Grupos de Referencia Competitiva Programme Projects GRC2015/009. F.Lucio thanks the Spanish Ministry of Education (grant FPU13/05014).


[1] (a) A. I. Matesanz, J. M. Pérez, P. Navarro, J. M. Moreno, E. Colacio, P. Souza, J. Inorg. Biochem. 1999, 76. (b) G. Domagk, Quimioteraia de la tuberculosis por las tiosemicarbazonas. Científico Médica, 1951. (c) M. T. Cocco, C. Congiu, V. Onnis, M. L. Pellerano , A. De Logu Bioorganic and Medicinal Chemistry, 2002, 10 501.

[2] (2) (a) C Preihs, D. Magda, J. Sessler J. Porphyrins and Phthalocyanines, 2011, 15, 539. (b) Z. Sun, M. Barboiu, Y-M Legrand, E. Petit, A. Rotaru, Angew. Chem. Int. Ed. 2015, 54, 14473

[3]  M. J. Frisch et alGaussian 09, Revision D.01; Gaussian, Inc., Wallingford CT, 2013.


Keywords: DFT, Crown Ethers, Thiosemicarbazones.