New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Main Authors: Maryna V. Murlykina, Maryna N. Kornet, Sergey M. Desenko, Svetlana V. Shishkina, Oleg V. Shishkin, Aleksander A. Brazhko, Vladimir I. Musatov, Erik V. Van der Eycken, Valentin A. Chebanov
• Format: Article
• Language: English
• Published: Beilstein-Institut 2017-05-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: 3-amino-5-methylisoxazole; 5-amino-N-aryl-1H-pyrazole-4-carboxamides; antibacterial activity; Groebke–Blackburn–Bienaymé reaction; isocyanide Ugi reaction
• Online Access: https://doi.org/10.3762/bjoc.13.104

The well-known aminoazoles, 3-amino-5-methylisoxazole and 5-amino-N-aryl-1H-pyrazole-4-carboxamides, were studied as an amine component in Ugi and Groebke–Blackburn–Bienaymé multicomponent reactions. The first example of an application of aminoazoles in an Ugi four-component reaction was discovered and novel features of a Groebke–Blackburn–Bienaymé cyclocondensation are established and discussed. The heterocycles obtained were evaluated for their antibacterial activity and several of them demonstrated a weak antimicrobial effect, but for most of the compounds a 30–50% increase in biomass of Gram-positive strains (mainly B. subtilis) compared to control was observed.