Synthesis and pharmacological activity of 5-aryl-4-acetyl-1-carboxyalkyl-tetrahydropyrrole-2,3-diones

Abstract

Previously we have reported on the antiinflammatory [1] and antiviral [2] properties of 1,4,5-trisubstituted tetrahydropyrrole-2,3 -diones.tn continuation of the search for biologically active compounds in the series of substituted tetrahydropyrrole-2,3-diones (structurally similar to pyracetam), it was of interest to attempt their synthesis by the method described in [2], using natural co-and 13-amino acids as the amino components, and study the nootropic, antibacterial, antiinflammatory, and analgesic activity.For this purpose we have studied the interaction of methyl ester of acetylpyruvic acid with a mixture of an aromatic aldehyde and amino acid. Our experiments showed that short-time heating of glycine (as the amino acid) in alcohol, followed by holding the reaction mixture at room temperature, leads to 5-aryl-4-acetyl-l-carboxyalkyltetrahydropyrrole-2,3-diones (I -V) with good yield.

Synthesis, Properties, and Antimicrobial Activity of 3-Hydrazones of 1-Aryl-5-methyl-1,5-ethoxycarbonylpyrrolidine-2,3-diones

“…Previously, we have reported that tetrahydropyrrole-2,3-diones substituted at positions 1, 4, and 5 of the heterocycle possess analgesic [1], nootropic [1], antiinflammatory [2], antibacterial [3], and antiviral activity [4]. In continuation of the search for biologically active compounds in the class of substituted pyrrolidine-2,3-diones, it was also of interest to obtain their 3-hydrazones and to study how this structural change will modify the chemical properties and antibacterial activity of pyrrolidine-2,3-diones.…”

Synthesis and Antibacterial Activity of 3,4-Diaryl-5-(4-Guanidylsulfonylphenyl)-4,6-Dihydropyrrolo[3, 4-C]Pyrazol-6-Ones

“…Substituted tetrahydropyrrol-2,3-diones are known to have antimicrobial, anti-inflammatory, analgesic, nootropic, and other types of activity [2,3].…”

Synthesis and biological activity of 5-aryl-4-acyl-3-hydroxy-1-morpholinoalkyl-3-pyrrolin-2-ones

“…Previously, we demonstrated that substituted 3-hydroxy-3-pyrrolin-2-ones possess pharmacological activity of various types, including antimicrobial [1 -3], antiinflammatory [4], analgesic [4,5], antiviral [6], and nootropic [3,5] in combination with relatively low toxicity. According to the published data, both the type and magnitude of activity depend on the character of the substituent in position 1 of the heterocycle [3,4].…”