Синтез та антимікробна активність 4-хлоро-5-(2-нітровініл)-1Н-імідазолів і продуктів їх взаємодії з 3-метил-2-піразолін-5-оном

• Date: 2014
• Main Authors: Chornous, V. O., Mel’nyk, O. Ya., Grozav, A. M., Yakovychuk, N. D., Vovk, M. V.
• Format: Article
• Language: Ukrainian
• Published: National University of Pharmacy 2014
• Subjects: 4-хлоро-5-формілімідазоли; нітроалкани; 3-метил-2-піразолін-5-он; 4-хлоро-5- (2-нітровініл)імідазоли; 4-[1-(4-хлороімідазол-5-іл)-2-нітроалкіл]-5-метил-1H-піразол-3-оли; протигрибкова та бактерицидна активність; УДК 547.79 547.781.4 615.31
• Online Access: https://ophcj.nuph.edu.ua/article/view/ophcj.14.808
• Journal Title: Journal of Organic and Pharmaceutical Chemistry

The work is devoted to the synthesis of new derivatives of 5-(2-nitrovinyl)imidazole, investigation of their chemical behaviour in the Michael reaction with heterocyclic CH-acids and study of their antifungal and antibacterial action. It has been found that 1-substituted 4-chloro-5-(2-nitrovinyl)imidazoles can be prepared with 71-83% yields by heating 4-chloro-5-formylimidazoles with the excess of nitromethane or nitroethane in the presence of anhydrous ammonium acetate. The compounds synthesized are typical representatives of activated alkenes and react with 3-methyl-2-pyrazolin-5-one in the Michael reaction. It has been shown that when refluxing in water for 3 h the interaction proceeds regioselectively with the most nucleophilic C4 atom of pyrazolinone giving 4-[1-(4-chloro-1H-imidazole-5-yl)-2-nitroalkyl]-5-methyl-1H-pyrazol-3-oles. In the case of the spatially hindered exocyclic part of the molecule 1H NMR spectra have characteristic features. The biological screening results of the compounds obtained have confirmed a high bactericidal and fungicidal effect. It has been found that antimicrobial properties are dependent on the nature of the substituent in the position 1 of the imidazole cycle and the structure of the exocyclic fragment. In particular, the condensation products of 4-chloroimidazol-5-carbaldehyde with nitroethane showed 4-6 times higher bactericidal activity compared to the analogous compounds obtained from nitromethane.