Site-Selectivity of the Reaction of 3-Amino-4-Cyano-5-Phenyl-1H-Pyrrole-2-Carboxylic Acid Amide with α-Halocarbonyl Compounds. Antimicrobial Activity and Docking Study for COVID-19 of the Products

In this context, we are interested to study the site-selectivity of the reaction of 3-amino-4-cyano-5-phenyl-1H-pyrrole-2-carboxylic acid amide 1 with different types of hydrazonoyl halides as well as the α-haloketones. The products of these reactions were confirmed from their spectral data and conformational studies to be pyrrolo[1,2-d][1,2,4]triazine and pyrrolo[1,2-a]pyrazine derivatives. We used docking studies to test the ability of the new synthesized pyrrolo[1,2-d][1,2,4]triazine and pyrrolo[1,2-a]pyrazine derivatives to dock and inhibit the microbes and COVID-19 proteins. The results of both docking studies revealed a strong fit of almost the tested derivatives into the active sites of peroxiredoxin 5 (Pdb: 2WFC; the overexpressed proteins in Candida albicans) and COVID-19 main protease (Pdb: 6LU7; severe acute respiratory syndrome coronavirus 2). Moreover, the antimicrobial activity of the products was investigated against two selected Fungi species and two G+ and two G− bacteria. The results of antimicrobial activity indicated that almost all derivatives showed no activity against fungi species, while all of them have moderate activity against bacteria strains (G+ and G− bacteria).