Compounds removed from the condensation reaction between 2-acetylpyridine and 2-formylpyridine. Synthesis, crystal structure and biological evaluation
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54-3.057:547:615.2 (1)
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RUSNAC, Roman; BOTNARU, Maria; BARBA, Nicanor; PETRENKO, Peter A.; CHUMAKOV, Yurii; GULEA, Aurelian. Compounds removed from the condensation reaction between 2-acetylpyridine and 2-formylpyridine. Synthesis, crystal structure and biological evaluation. In: Chemistry Journal of Moldova. 2020, nr. 2(15), pp. 88-98. ISSN 1857-1727.
10.19261/cjm.2020.695
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Chemistry Journal of Moldova
Numărul 2(15) / 2020 / ISSN 1857-1727 /ISSNe 2345-1688

Compounds removed from the condensation reaction between 2-acetylpyridine and 2-formylpyridine. Synthesis, crystal structure and biological evaluation


CZU: 54-3.057:547:615.2
DOI: 10.19261/cjm.2020.695
Pag. 88-98

Rusnac Roman1, Botnaru Maria1, Barba Nicanor1, Petrenko Peter A.2, Chumakov Yurii23, Gulea Aurelian1
 
1 State University of Moldova,
2 Institute of Applied Physics,
3 Gebze Technical University
 
Disponibil în IBN: 30 decembrie 2020


Rezumat

The research is devoted to the study of unexpected products that formed as a result of the condensation reaction between 2-acetylpyridine and 2-formylpyridine under the Claisen-Schmidt reaction conditions. The structure of the compounds was determined and confirmed using FTIR, 1H and 13C NMR spectroscopy, and X-ray diffraction technique. As a result, a sequence of reactions leading to the following compounds has been proposed: 1,3-bis(pyridin-2-yl)prop-2-en-1-one (3); 1,3,5-tri(pyridin-2-yl)pentane-1,5-dione (4); (2,4-dihydroxy-2,4,6-tri(pyridin-2-yl)cyclohexyl)(pyridin-2-yl)methanone (5) and (4-hydroxy-2,4,6-tri(pyridin-2-yl)cyclohexane-1,3-diyl)bis(pyridin-2-ylmethanone) (6) as well as 2-formylpyridine (1) and 2-acetylpyridine (2). The plausible mechanisms of these chemical transformations and synthetic methods for obtaining substituted cyclohexanol derivatives are also presented. The synthesized compounds were tested for antimicrobial and antioxidant activity. The obtained results show that the compounds 4-6 have moderate antifungal activity. The activity of compound 6 is nine times higher towards Cryptococcus neoformans than the activity of Nistatin that is used in medical practice. The present experimental results show that compound 6 has potential application in antibacterial and antifungal areas.

Cuvinte-cheie
1, 3-bis(pyridin-2-yl)prop-2-en-1-one, Claisen-Schmidt condensation, intramolecular aldol condensation, Michael addition, substituted cyclohexanol