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Synthesis and fungistatic activity of aryl-substituted naphthalene- and indene-2-carbonitriles

Kozik B, Burgieł Z. J., Sepioł J. J., Wilamowski J., Łuczyński M. K., Góra M.

Environmental Biotechnology

2006

Vol. 2, No. 1

20-25

4-Aryl-substituted 1-aminonaphthalene-2-carbonitriles and 3-phenyl-1-oxo-1H-indene-2-carbonitriles were prepared in a two--step synthesis from appropriate carbonyl compounds and were evaluated in vitro for growth-inhibiting activity against some phytopathogenic fungi: Fusarium culmorum, Penicillium expansum, Botrytis cinerea and Alternaria species. The results were compared with the activity of a commercial fungicide - captan. The highest fungistatic activity was revealed by 1-amino-4-phenylnaphthalene-2-carbonitrile. An efficient synthesis of 1-amino-4-arylnaphthalene-2-carbonitriles involves condensation of diarylacetaldehydes or 1,1-diarylacetones with malonodinitrile and cyclization of the obtained aryl-ylidenemalonodinitriles in concentrated sulfuric acid. The benzannulation reaction is accompanied by a quasi-aromatic rearrangement. The indenone derivatives were synthesized in the same manner from substituted benzophenones. As the formation of five-membered ring during the cyclization of diarylmethylidenemalonodinitriles was less effective, the rearrangement was not observed.

Oxidative metabolism, mutagenic and carcinogenic properties of some polycyclic aromatic hydrocarbons

Łuczyński M. K., Góra M., Brzuzan P., Wilamowski J., Kozik B.

Environmental Biotechnology

2005

Vol. 1, No. 1

16--28

This attempt to synthesize the present state of knowledge on the correlation between the structure of chosen PAHs and their mutagenic or carcinogenic activity shows that the dependencies cannot be treated univocally. Extreme complexity of the subject, typical for investigations on the boundary between chemistry and biology, inclines one to search for new ways of synthesis of new compounds, which would be of interest for biologists studying the problem of chemical carcinogenesis. On the other hand, there is a strong need for elaborating a standardized test that would explicitly define the carcinogenic properties of a specific compound. The use of a variety of methods for the determination of carcinogenic potency of chemical compounds combined with simultaneous differentiation of structure of examined compounds, sometimes leads to contradictory conclusions. Correlation between mutagenic and carcinogenic activity of some compounds is also sometimes questionable. Modern molecular biology should allow for elaborating a method which would give a satisfactory and reliable answer to the fundamental question: is a specific compound carcinogenous for a human organism? And if so - to what extent?