Evaluation of Antiradical Activity and Reducing Capacity of Synthesised Bispyridinium Dibromides Obtained by Quaternisation of 4-Pyridyl-1,4-dihydropyridines with Propargyl Bromide

Martins Rucins; Marina Gosteva; Sergey Belyakov; Arkadij Sobolev; Karlis Pajuste; Mara Plotniece; Brigita Cekavicus; Dace Tirzite; Aiva Plotniece

doi:10.1071/CH14033

RESEARCH ARTICLE

Evaluation of Antiradical Activity and Reducing Capacity of Synthesised Bispyridinium Dibromides Obtained by Quaternisation of 4-Pyridyl-1,4-dihydropyridines with Propargyl Bromide

Martins Rucins ^A ^B , Marina Gosteva ^A , Sergey Belyakov ^A , Arkadij Sobolev ^A , Karlis Pajuste ^A , Mara Plotniece ^A , Brigita Cekavicus ^A , Dace Tirzite ^A and Aiva Plotniece ^A ^C

+ Author Affiliations

- Author Affiliations

^A Latvian Institute of Organic Synthesis, Aizkraukles str. 21, Riga, LV-1006, Latvia.

^B Faculty of Medicine, University of Latvia, Raina blvd. 19, Riga, LV-1586, Latvia.

^C Corresponding author. Email: aiva@osi.lv

Australian Journal of Chemistry 68(1) 86-92 https://doi.org/10.1071/CH14033
Submitted: 28 January 2014 Accepted: 27 March 2014 Published: 7 May 2014

Abstract

New bispyridinium dibromides based on the 1,4-dihydropyridine (1,4-DHP) cycle were synthesised in the reaction between 4-pyridyl-1,4-DHP derivatives and propargyl bromide. It has been shown that variation of the substituent position on the pyridine as well as small changes in the electronic nature of the 1,4-DHP cycle as a result of the substituent nature at the 3 and 5 positions do not affect the course of the reaction and in all cases the corresponding bispyridinium dibromides 4a–e were formed. The antiradical activity, using 1,1-diphenyl-2-picrylhydrazine as a free radical scavenger, and the reducing capacity using phosphomolybdenum complexes have been evaluated for the newly synthesised compounds 4a–e. It has been shown that all tested 1,4-DHP bispyridinium dibromides 4a–e possess reducing capacity and antiradical properties. Moreover, the reducing capacity results could be explained by the influence of the electronic nature of the substituent at the 3 and 5 positions of the 1,4-DHP cycle.

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Evaluation of Antiradical Activity and Reducing Capacity of Synthesised Bispyridinium Dibromides Obtained by Quaternisation of 4-Pyridyl-1,4-dihydropyridines with Propargyl Bromide

Abstract

References

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