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

Tumosienė, Ingrida; Kantminienė, Kristina; Jonuškienė, Ilona; Peleckis, Artūras; Belyakov, Sergey; Mickevičius, Vytautas

doi:10.3390/molecules24050971

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

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Department of Organic Chemistry, Kaunas University of Technology, LT-50254 Kaunas, Lithuania

Department of Physical and Inorganic Chemistry, Kaunas University of Technology, LT-50254 Kaunas, Lithuania

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

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

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

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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. https://doi.org/10.3390/molecules24050971

AMA Style

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(5):971. https://doi.org/10.3390/molecules24050971

Chicago/Turabian Style

Tumosienė, Ingrida, Kristina Kantminienė, Ilona Jonuškienė, Artūras Peleckis, Sergey Belyakov, and Vytautas Mickevičius. 2019. "Synthesis of 1-(5-Chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives and Their Antioxidant Activity" Molecules 24, no. 5: 971. https://doi.org/10.3390/molecules24050971

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

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