Synthesis of Novel Benzimidazoles 2-Functionalized with Pyrrolidinone and γ-Amino Acid with a High Antibacterial Activity

Synthesis and Antibacterial Activity of New Azole, Diazole and Triazole Derivatives Based on p-Aminobenzoic Acid

“…With a great affinity displayed towards a numerous enzymes and receptors, the benzimidazoles could be potentially explored for the development of new pharmaceuticals. Numerous studies revealed that compounds derived from a benzimidazole nucleus exhibit analgesic and anti-inflammatory activity [ 41 ], as well as antiulcerative [ 42 ], anticancer [ 43 ], antiparasitic [ 44 ], antimicrobial [ 45 , 46 , 47 ], antioxidant [ 46 ], anticonvulsant [ 48 ], anticancer/antiestrogenic [ 49 , 50 ], antihypertensive [ 51 ], antifouling [ 52 ], and many others [ 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 ] activities. Therefore, the strategies of developing compounds bearing the benzimidazole scaffold should be further explored to generate pharmacologically active molecules.…”

“…Methyl 4-(4-((2,5-dimethyl-1H-pyrrol-1-yl)carbamoyl)-2-oxopyrrolidin-1-yl)benzoate (6): To a solution of hydrazide 4 (3,48 g, 12.5 mmol) in ethanol (15 mL), 2,5-hexanedione (1.85 mL, 15.8 mmol) and glacial acetic acid (2 mL) were added by stirring, and the mixture was heated at reflux for 1,5 h. Then the reaction mixture was cooled down, and the formed crystalline solid was filtered off, washed with ethanol and ether, and recrystallized from methanol to give the title compound 6 (yellowish solid, yield 2.11 g,47.5%, m. p. 147-148 • C). 1 H-NMR (400 MHz, DMSO-d 6 ): δ = 2.00 (s, 6H, 2CH 3 ), 2.74-3.01 (m, 2H, COCH 2 ), 3.46-3.54 (m, 1H, CH), 3.84 (s, 3H, OCH 3 ), 3.98-4.22 (m, 2H, NCH 2 ), 5.65 (s, 2H, 2C=CH), 7.85 (d, J = 8.8 Hz, 2H, H ar ), 7.97 (d, J = 8.8 Hz, 2H, H ar ), 10.94 (s, 1H, NH) ppm.…”

Synthesis of 1-(5-Chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives and Their Antioxidant Activity

“…8-C N -Ethyl-2-pyrrolidinone substituted flavan-3-ols isolated from the aqueous extract of pu-erh tea have been proven to possess antioxidant activity [ 5 ]. Pyrrole derivatives comprise a class of biologically active heterocyclic compounds which can serve as promising scaffolds for agents possessing antioxidant [ 3 , 6 , 7 ], anticancer, anti-depressant, anti-inflammatory, anti-malarial, anti-HIV, antibacterial [ 8 ], anti-tubercular, anti-ulcer, anti-hypertensive, insecticidal, cytotoxic, and antiviral [ 9 , 10 ] properties.…”

Nucleophilic ring opening of 1,4-disubstituted 2-pyrrolidones with hydrazine. Synthesis of azoles with a high antibacterial activity

“…Also, the compounds whose molecules possess an azole ring, such as pyrrole [11][12][13], 1,3,4-oxadiazole [14][15][16][17][18][19] and 1,2,4-triazole [19][20][21][22][23], are often characterized as good antimicrobial agents. In our previous works [24][25][26][27], we have reported that the heating under reflux of 4-(1H-benzimidazol-2-yl)-1-(substituted phenyl)pyrrolidin-2-ones in a 20% aqueous sodium hydroxide solution leads to the opening of the 2-pyrrolidinone cycle, followed by the formation of sodium salts of the corresponding N-substituted γ-amino acids. These acids are obtained by acidifying the corresponding salt solutions with acetic acid and can be easily cyclized to the initial pyrrolidin-2-ones under the influence of heat or mineral acids.…”