Synthesis and Antimicrobial Activity of 3-Hydroxy- and 3-Arylamino-5-aryl-4-acyl-1-(pyridyl)-3-pyrrolin-2-ones

Previously we reported on the synthesis of 3-hydroxy-3pyrrolin-2-ones containing aromatic substituents in position 5 and aroyl [1 – 4] or arylsulfonyl [2, 5] in position 4. It was found that these compounds possess, depending on the character of substituent in position 1 of the heterocycle, antimicrobial [6], antiviral [6, 7], analgesic [6], and antiamnesic [8] properties. For elucidating the influence of the character of substituents in position 1 on the biological activity of 3-pyrrolin-2ones, especially on their antimicrobial properties, it was of interest to introduce a pyridine residue into this position. In order to obtain 5-aryl-4-acyl-1-(2-pyridyl)-3-hydroxy-3-pyrrolin-2-ones (I – XV), we have studied the reactions of acylpyruvic acid esters with a mixture of aromatic aldehydes and 2-aminopyridine or 5-bromo-2-aminopyridine. R = H (XVI, XVII), CH3 (XVIII), Br (XIX), C2H5O (XX), CH3O (XXI); R 1 =C H 3 (I – V, XVI), C6H5 (VI – XI, XVII – XXI), 4-BrC6H4 (XII, XIII),