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Synthesis and biological activity of novel N,N-cyclic-2,4-dihydroxythiobenzamide derivatives

Joanna Matysiak 1,  Alicja Skrzypek 1,  Urszula Głaszcz 1,  Joanna Wietrzyk 2,  Elżbieta Krajewska-Kułak 3,  Andrzej Niewiadomy 1

1. University of Life Sciences, Department of Chemistry, Akademicka 15, Lublin 20-950, Poland
2. Polish Academy of Sciences, Institute of Immunology and Experimental Therapy (IITD), Rudolfa Weigla 12, Wrocław 53-114, Poland
3. Medical University of Bialystok, Department of Integrated Medical Care, Marii Skłodowskiej-Curie 7A, Białystok 15-096, Poland

Abstract
Benzanilide (N-phenylbenzamide) derivatives possess a broad spectrum of biological activities. They have been found to exhibit antimalarial, antibacterial and antifungal properties [1-3]. Derivatives of N-(2-hydroxyphenyl)benzamide have been  studied for the last few years as the possible metabolites of the antibacterial active benzo[d]oxazole derivatives [4]. Some benzanilide derivatives have been reported to inhibit the c-Met tyrosine kinase receptor, which is a potentially important target for the treatment of cancer [5].
The aim of presented work was the synthesis of new N,N-cyclic-2,4-dihydroxythiobenzamide derivatives with potential antifungal and antiproliferative  activity against human cancer cells. The synthesis of the desired compounds were achieved by reacting of the sulfinylbis((2,4-dihydroxyphenyl)methanethione (STB) with secondary amines. Purity of compounds was monitored by the reversed-phase (RP-18) HPLC chromatography (MeOH – water). The structure of compounds was confirmed by IR, 1H NMR, 13C NMR spectroscopy and mass spectrometry.

The tested compounds inhibited proliferation of tumor cells derived from human bladder cancer line (HCV29T). Cisplatin was used as a reference drug. The cytotoxic activity in vitro was expressed as IC50 and  was at the level of 10.51 – 33.98 μg.ml-1. Antifungal properties were evaluated against different strains of Candida.

References:

1. Desai K.R. Shaikh M.S., et al., Med. Chem. Res., 20, 321, (2011).
2. Ertan T., Yildiz S., et al., Bioorg. Med. Chem., 15, 2032, (2007).
3. Niewiadomy A., Matysiak J., Mącik-Niewiadomy G., Eur. J. Pharm. Sci., 13, 243, (2001).
4. Oren I.Y., Aki-Sener E., et al., Turk. J. Chem., 28, 441, (2004).
5. Allen J.V. Bardelle C. et al., Bioorg. Med. Chem. Lett., 21, 5224 (2011).

 

 

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Presentation: Poster at IX Multidyscyplinarna Konferencja Nauki o Leku, by Joanna Matysiak
See On-line Journal of IX Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2014-03-14 16:46
Revised:   2014-05-02 12:55