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THE STUDY OF SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME NEW 1,4- DIAZINIUM DERIVATIVES

AUTHOR/S: M. UNGUREANU, A. POIATA, C. TUCHILUS, I. I. MANGALAGIU
Sunday 1 August 2010 by Libadmin2008

8th International Scientific Conference - SGEM2008, www.sgem.org, SGEM2008 Conference Proceedings/ ISBN: 954-918181-2, June 16-20, 2008, Vol. 2, 381-388 pp

ABSTRACT

In previous papers, we emphasised the important antimicrobial properties of some
pyrazine and quinoxaline derivatives. In order to extend the research in the 1,4-diazine
series, in this study we investigate the synthesis and amtimicrobial properties of some
pyrazine and 6-methyl-quinoaline new derivatives. To this stage, we synthesised
various cycloimmonium salts with acetophenone skeleton. On further treatment of
diazinium salts in alkaline medium, we obtained ylidic intermediates. The existence in
situ of ylids was made evident through the 3+2 dipolar cicloaddition with
dipolarophiles, activated alkynes and alkenes. Twelve new azabicyclic derivatives were
obtained. The chemical structures of new compounds was confrmed by C,H,N
elemental analysis and by spectral analysis.We tested the antibacterial and antifungal
activity of 15 new synthesised diazinium derivatives, cycloimmonium salts and
azabicyclic products. The assay was made on the following eight microorganisms:
Staphyloccocus aureus, Bacillus subtillis, Bacillus cereus, Sarcina lutea Escherichia
Coli, Candida albicans, Candida sake, Candida glabrata. The in vitro antimicrobial
tests was performed using the disc diffusimetric method established by the National
Committee for Clinical Laboratory Standards (NCCLS) (Document M7-A2, 1990).
Medium: Mueller-Hinton agar (Oxoid). The inhibitory activity of these compounds was
assessed by comparing it with the following witnesses: Tetracycline (for germs) and
Nytsatin (for fungus). Regarding the zones of inhibition, the diameters of the growth
inhibition zone (in mm) were measured after 24h of incubation at 35 oC. With regards to
the relations between the chemical structure and and the antimicrobial activity, it was
proved that the most active are the cycloaducts derived from 1,4- diazines. The results
show that these research present a premise for obtaining new antibacterial and
antifungal compounds of pyrazine and quinoxaline series.

Keywords: 1,4 diazine derivatives, antimicrobial activity, diffusimetric method