Synthesis and Antibacterial Activity of 1-(4-Aminosulfonylphenyl)-5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones
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SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 1-(4-AMINOSULFONYLPHENYL)-5-ARYL-4-ACYL-3HYDROXY-3-PYRROLIN-2-ONES V. L. Gein,1 T. F. Odegova,1 K. A. Tkachenko,1 O. V. Bobrovskaya,1 and M. I. Vakhrin1 Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 47, No. 7, pp. 31 – 33, July, 2013. Original article submitted July 12, 2012.
Interaction of 4-aminobenzenesulfamide with a mixture of an aromatic aldehyde and the methyl ester of an acylpyruvic acid was used to prepare 1-(4-aminosulfonylphenyl)-5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones. The antibacterial activity of these compounds was studied. Keywords: 1-(4-aminosulfonylphenyl)-5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones, synthesis, antibacterial activity.
dimethylsulfoxide and dimethylformamide, and with -d6 in glacial acetic acid and dioxane, but poorly soluble in ethanol and insoluble in water. The structures of the compounds synthesized here were confirmed by 1H NMR and IR spectroscopy. The 1H NMR spectra of compounds I – XII contained signals from aromatic protons in the form of multiplets at 6.83 – 8.09 ppm, a singlet from the heterocycle position 5 methine proton at 6.00 – 6.56 ppm, a singlet from the pyrroline ring position 3 hydroxyl group at 10.81 – 10.85 ppm, and signals from primary amino group protons among the aromatic proton sig-
The pyrrolidin-2,3-dione ring is one of the most interesting systems in chemical, physicochemical, and biological studies. A number of drugs used in medicine are pyrrolidin2-one (piracetam) and tetrahydropyrrole (lincomycin hydrochloride, clindamycin hydrochloride, captopril, etc.) derivatives [1]. Substituted tetrahydropyrrol-2,3-diones are also known to display anti-inflammatory, analgesic, nootropic, and other activities [2, 3]. Continuing our studies related to the synthesis of 3-hydroxy-3-pyrrolin-2-ones, we have prepared tetrahydropyrrol-2,3-diones with a aminosulfonylphenyl substituent at position 1 of the heterocyclic ring. Compounds I – XII were synthesized using a published method [4] in a three-component reaction between acylpyruvic acid methyl ester, aromatic aldehydes, and 4-aminobenzenesulfamide in glacial acetic acid (I – VIII) or acetonitrile (IX – XII (method A). Compounds I – XII were also prepared using a two-step procedure: reaction of 4-aminobenzenesulfamide with aromatic aldehydes produced Schiff bases, which were then interacted with acetyl(benzoyl)pyruvic acid methyl ester. Boiling of equimolar quantities of the corresponding Schiff base and acetyl(benzoyl)pyruvic acid methyl ester in glacial acetic acid or acetonitrile was found to form 1-(4-aminosulfonylphenyl)-5-aryl-4-acetyl(benzoyl)-3-hydroxy-3-pyrrolin -2-ones (I – XII) (method B) (Table 1). The resulting compounds, I – XII, were white, pale yellow, or cream-colored crystalline substances, soluble in 1
TABLE 1. Constants and Yields of Compounds I-XII. Yield, % a
b
Melting temperature, °C
Atomic formula
46 56 45 59 71 76 66 45 71 73 65 69
47 59 53 45 60 71 75 52 47 65 63 53
243 – 245 235 – 236 240 – 242 232 – 234 273 – 275 238 – 240 253 – 2
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