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Molecules 2019, 24(5), 971; https://doi.org/10.3390/molecules24050971

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

1
Department of Organic Chemistry, Kaunas University of Technology, LT-50254 Kaunas, Lithuania
2
Department of Physical and Inorganic Chemistry, Kaunas University of Technology, LT-50254 Kaunas, Lithuania
3
Laboratory of Physical Organic Chemistry, Latvian Institute of Organic Synthesis, Aizkraukles 21, 1006 Riga, Latvia
*
Author to whom correspondence should be addressed.
Academic Editors: Carmela Saturnino and Derek McPhee
Received: 4 February 2019 / Revised: 4 March 2019 / Accepted: 5 March 2019 / Published: 9 March 2019
(This article belongs to the Special Issue Synthesis and Characterization of Heterocyclic Compounds)
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Abstract

A series of novel 1-(5-chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives containing chloro, hydroxyl, isopropyl, nitro, nitroso, and amino substituents at benzene ring and 1-(5-chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carbohydrazide derivatives bearing heterocyclic moieties were synthesized. Antioxidant activity of the synthesized compounds was screened by DPPH radical scavenging method and reducing power assay. A number of compounds were identified as potent antioxidants. Antioxidant activity of 1-(5-chloro-2-hydroxyphenyl)-4-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyrrolidin-2-one has been tested to be 1.5 times higher than that of a well-known antioxidant ascorbic acid. 1-(5-Chloro-2-hydroxyphenyl)-4-(4-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyrrolidin-2-one has shown 1.35 times higher antioxidant activity than that of vitamin C by DPPH radical scavenging method and optical density value of 1.149 in reducing power assay. The structure of 1-(5-chloro-2-hydroxyphenyl)-N-(1,3-dioxoisoindolin-2-yl)-5-oxopyrrolidine-3-carboxamide was unambiguously assigned by means of X-ray diffraction analysis data. View Full-Text
Keywords: pyrrolidin-2-one; azoles; antioxidative; X-ray pyrrolidin-2-one; azoles; antioxidative; X-ray
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Tumosienė, I.; Kantminienė, K.; Jonuškienė, I.; Peleckis, A.; Belyakov, S.; Mickevičius, V. Synthesis of 1-(5-Chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives and Their Antioxidant Activity. Molecules 2019, 24, 971.

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