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Ebselen analogues: synthesis and antimicrobial activity

Magdalena Piętka-Ottlik 1,  Anna Krasowska 2,  Anna Jaromin 3

1. Wroclaw University of Technology, Faculty of Chemistry, Organic and Pharmaceutical Technology Group, Wybrzeze Wyspianskiego 27, Wrocław 50-370, Poland
2. University of Wroclaw, Faculty of Biotechnology, Department of Biotransformation, Joliot-Curie 14A, Wrocław 50-383, Poland
3. University of Wroclaw, Faculty of Biotechnology, Department of Lipids and Liposomes, Joliot-Curie 14A, Wrocław 50-383, Poland

Abstract
Ebselen and its organoselenium analogues are well known as active immunostimulants, inhibitors of enzymes, antioxidants, anti-inflammatory, antitumor, antiviral and antimicrobial agents1-6.
In this work we report synthesis and results of biological evaluation of a series of C substituted ebselen analogues (Fig.1).


The general strategy for the synthesis of C-substituted benzisoselenazol-3(2H)-ones is based on the conversion of commercially available 5 substituted 2-chlorobenzoic acids or 2-aminobenzoic acids into 5-substituted 2 (chloroseleno)benzoyl chlorides and finally on the tandem selenenylation-acylation of primary amines with these reagents. Prepared compounds were tested towards inhibition of the viability of gram positive (Bacillus subtilis), gram negative (Escherichia coli) bacteria and pathogenic fungus Candida albicans. The preliminary results indicate the promising, anti-bacterial and anti-mycotic activity of tested compounds in low concentrations.

References:

1. Mugesh G. et al., Chem. Rev., 101, 2125 (2001),
2. Mugesh G. et al., Chem. Soc. Rev., 29, 347 (2000),
3. Nogueira CW. et al., Arch Toxicol.,11, 1313 (2011),
4. Wojtowicz H. et al., Il Farmaco, 58(12), 1235 (2003),
5. Wojtowicz H. et al., Il Farmaco, 59(11), 863 (2004),
6. Piętka-Ottlik M., et al., Chem Pharm Bull, 56.1423 (2008).

This work was financially supported by the National Science Centre (NCN) under grant no. UMO-2013/09/D/ST5/03814.
 

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

Submitted: 2014-04-08 07:42
Revised:   2014-05-02 10:49