Synthesis and Biological Activity of 3-[Phenyl(1,3-thiazol-2-yl)-amino]propanoic Acids and Their Derivatives

Mickevičius, Vytautas; Voskienė, Aušra; Jonuškienė, Ilona; Kolosej, Ramūnė; Šiugždaitė, Jūratė; Venskutonis, Petras Rimantas; Kazernavičiūtė, Rita; Brazienė, Zita; Jakienė, Elena

doi:10.3390/molecules181215000

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Article

5 December 2013

19 Pages

Synthesis and Biological Activity of 3-[Phenyl(1,3-thiazol-2-yl)-amino]propanoic Acids and Their Derivatives

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Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, Lithuania

Lithuanian University of Health Sciences, Veterinary Academy, Tilžės 18, LT-47181 Kaunas, Lithuania

Department of Food Technology, Kaunas University of Technology, Radvilėnų pl. 19, LT-50254 Kaunas, Lithuania

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Lithuanian Research Centre for Agriculture and Forestry, Rumokai Experimental Station, Klausučiai, 70462 Vilkaviškis Distr., Lithuania

Molecules2013, 18(12), 15000-15018;https://doi.org/10.3390/molecules181215000

This article belongs to the Section Organic Chemistry

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Abstract

New N,N-disubstituted β-amino acids and their derivatives with thiazole, aromatic, and heterocyclic substituents were synthesized from N-phenyl-N-thiocarbamoyl-β-alanine by the Hantzsch method; derivatives with hydrazone fragments were also obtained. Some of the synthesized compounds exhibited discrete antimicrobial activity, and 3-[(4-oxo-4,5-dihydro-1,3-thiazol-2-yl)(phenyl)amino]propanoic acid was found to promote rapeseed growth and to increase seed yield and oil content.

Keywords:

N-phenyl-N-thiocarbamoyl-β-alanine; Hantzsch synthesis; thiazole; hydrazone; biological activity

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