Synthesis and antimicrobial activity of 1-(4-hydroxyphenyl)-4-acyl-5-aryl-3-hydroxy-3-pyrrolin-2-ones

Abstract

The reaction of methyl esters of acylpyruvic acids, 4-aminophenols, and aromatic aldehydes leads to the formation of 1-(4-hydroxyphenyl)-4-acyl-5-aryl-3-hydroxy-3-pyrrolin-2-ones. The proposed structures of the synthesized compounds were confirmed by IR and PMR spectroscopy. The antibacterial activity of some of the newly synthesized compounds was studied.Substituted tetrahydropyrrol-2,3-diones have previously been found to exhibit various types of biological activity [1]. It seemed interesting to introduce into the 1-position of the heterocycle a phenol group and to study how this might affect the antimicrobial activity of the resulting compounds. I (R 1 = Ph, R 2 = H), II (R 1 = CH 3 , R 2 = H), III (R 1 = CH 3 , R 2 = 4-Cl), IV (R 1 = Ph, R 2 = 4-Cl), V (R 1 = CH 3 , R 2 = 2-NO 2 ), VI (R 1 = CH 3 , R 2 = 2-OCH 3 ), VII (R 1 = CH 3 , R 2 = 4-CH 3 ), VIII (R 1 = CH 3 , R 2 = 3-NO 2 ), IX (R 1 = CH 3 , R 2 = 2-Cl), X (R 1 = CH 3 , R 2 = 2,5(OCH 3 ) 2 ), XI (R 1 = CH 3 , R 2 = 2-F), XII (R 1 = CH 3 , R 2 = 4-C 3 H 7 ), XIII (R 1 = CH 3 , R 2 = 4-NO 2 ), XIV (R 1 = CH 3 , R 2 = 3-OCH 3 ), XV (R 1 = CH 3 , R 2 = 3-OH), XVI (R 1 = CH 3 , R 2 = 4-F), XVII (R 1 = CH 3 , R 2 = 3-OCH 3 -4-OH), XVIII (R 1 = CH 3 , R 2 = 3-F), XIX (R 1 = Ph, R 2 = 3,4-(OCH 3 ) 2 ), XX (R 1 = Ph, R 2 = 2-NO 2 ), XXI (R 1 = Ph, R 2 = 3-NO 2 ), XXII (R 1 = 4-CH 3 , R 2 = 4-CH 3 ), XXIII (R 1 = 4-CH 3 , R 2 = Ph), XXIV (R 1 = 4-CH 3 , R 2 = 3-F), XXV (R 1 = 4-CH 3 , R 2 = 2-Cl), XXVI (R 1 = 4-CH 3 , R 2 = 4-NO 2 ), XXVII (R 1 = Ph, R 2 = Ph), XXVIII (R 1 = 4-CH 3 , R 2 = 4-F), XXIX (R 1 = 4-CH 3 , R 2 = 4-Br), XXX (R 1 = 4-CH 3 , R 2 = 4-OCH 3 ).

Synthesis of pyrrolidinone derivatives from aniline, an aldehyde and diethyl acetylenedicarboxylate in an ethanolic citric acid solution under ultrasound irradiation

“…174-177°C. IR: ν max /cm −1 3250, 3077, 2970, 1710, 1458, 1090 cm −1 ; 1 H NMR (250.13 MHz, CDCl 3 ) δ H 1.16 (t, 3H, J = 7.00 Hz, 3H), 4.17 (q, J = 7.00 Hz, 2H), 5.74 (s, 1H), 7.05-7.50 (m, 9H), 9.14 (br s, 1H); 13…”

“…2-Pyrrolidinone-containing natural products display extremely interesting biological activities. 13 C NMR spectra of the products, the X-ray structure analysis and 1 H NMR spectra of the crude product. CCDC 1429951.…”

“…8 (−)-Azaspirene (6) is a novel angiogenesis inhibitor that is isolated from the fungus Neosartorya sp. 9 Substituted 3-pyrrolin-2-ones with a 2-pyrrolidinone moiety are also of use in medicinal chemistry as many derivatives have shown significant pharmacological and biological activities, as, e.g., anti-cancer agents, 10 antitumours, 11 HIV-1 integrase inhibitors, 12 anti-microbial, 13 antibacterial 14 and anti-inflammatory. 15 In view of the importance of substituted pyrrolidinones, various synthetic methods have been reported.…”

Synthesis and antibacterial evaluation of novel 1-(2,6-diethylphenyl)-5-oxopyrrolidine derivatives

“…Many substituted 2-pyrrolidinones are synthesized over a long period of their research, and abundance of the synthetic ones demonstrate a wide variety of healing properties such as anti-HIV [4][5][6], antiarrhythmic, hypotensive, antihypertensive [7,8], anticancer and antitumour [9][10][11][12][13], anti-inflammatory [14], anti-obesity [15], antiepileptic [16], antimicrobial [17], are used as antagonist of ETB [18], and others [19][20][21][22][23]. This moiety is a component of many synthetic pharmaceuticals (levetiracetam, medication for treatment epilepsy, pramiracetam, known as Pramistar, is a central nervous system stimulant and nootropic agent, doxapram hydrochloride, marketed as Dopram (Fig.…”

Microwave-assisted synthesis of pyrrolidinone derivatives using 1,1’-butylenebis(3-sulfo-3H-imidazol-1-ium) chloride in ethylene glycol

“…2-Pyrrolidinone derivatives substituted in position-4 were able to reduce the extracellular glutamate level, therefore effective for the prophylaxis and treatment of a large number of disorders such as stroke [19]. This fascinating scaffold has diverse pharmacological activities including antibacterial, antifungal, anticancer and anticonvulsant [20][21][22][23]; therefore, many procedures for the preparation of substituted pyrrolidinone have been reported and also their various reactions offer great scope in the field of medicinal chemistry [24][25][26][27][28][29][30].…”