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Comptes Rendus Chimie
Volume 18, n° 4
pages 399-409 (avril 2015)
Doi : 10.1016/j.crci.2014.09.007
Received : 1 May 2014 ;  accepted : 22 September 2014
Selenopheno[3,2-c ]- and [2,3-c ]coumarins: Synthesis, cytotoxicity, angiogenesis inhibition, and antioxidant properties
 

Pavel Arsenyan a, , Jelena Vasiljeva a, Irina Shestakova a, Ilona Domracheva a, Elina Jaschenko a, Nadezhda Romanchikova a, Ainars Leonchiks b, Zhanna Rudevica b, Sergey Belyakov a
a Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia 
b Latvian Biomedical Research and Study Centre, Ratsupites 1, 1067 Riga, Latvia 

Corresponding author at: Department of Medicinal chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia.
Abstract

A simple method for the synthesis of substituted selenopheno[2,3-c ] and -[3,2-c ]coumarins by treatment of the corresponding ethynylcoumarins with in situ prepared selenium(IV) bromide in 1,4-dioxane-water was elaborated. Molecular structures for selected derivatives were confirmed by X-ray diffraction measurements. The cytotoxic activity of novel selenophenocoumarins showed higher activity and lower acute toxicity than sodium selenite on various tumor cell lines as well as an ability for inhibiting matrix metalloproteinases (MMP-1 – MMP-14), angiogenesis on matrigel in vitro and in vivo . The compounds exhibit antioxidant and prooxidant properties.

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Keywords : Angiogenesis, Antioxidant, Coumarin, Cytotoxic activity, Selenium, Selenophene




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