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Molecules 2017, 22(6), 894; doi:10.3390/molecules22060894

Synthesis and Free Radical Scavenging Activity of New Hydroxybenzylidene Hydrazines

1
Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Ilkovicova 6, 842 15 Bratislava, Slovakia
2
Department of Chemistry, Faculty of Natural Sciences, Matej Bell University, Tajovskeho 40, 974 01 Banska Bystrica, Slovakia
3
Institute of Process Engineering, Faculty of Mechanical Engineering, Slovak University of Technology in Bratislava, Namestie slobody 17, 812 31 Bratislava, Slovakia
4
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Ilkovicova 6, 842 15 Bratislava, Slovakia
5
Department of Genetics, Faculty of Natural Sciences, Comenius University in Bratislava, Ilkovicova 6, 842 15 Bratislava, Slovakia
6
Department of Chromosome Biology, Max F. Perutz Laboratories, University of Vienna, Dr. Bohr-Gasse 9, 1030 Vienna, Austria
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Received: 7 April 2017 / Revised: 25 May 2017 / Accepted: 26 May 2017 / Published: 29 May 2017
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Hydroxybenzylidene hydrazines exhibit a wide spectrum of biological activities. Here, we report synthesis and free radical scavenging activity of nine new N-(hydroxybenzylidene)-N′-[2,6-dinitro-4-(trifluoromethyl)]phenylhydrazines. The chemical structures of these compounds were confirmed by 1H-NMR, 13C-NMR, 19F-NMR, IR spectroscopy, LC-MS, and elemental analysis. The prepared compounds were tested for their activity to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH), galvinoxyl radical (GOR), and 2,2′-azino-bis(3-ethylbenzothiazoline)-6-sulphonic acid (ABTS) radicals. The free radical scavenging activity expressed as SC50 values of these compounds varied in a wide range, from a strong to no radical scavenging effect. The most effective radical scavengers were hydroxybenzylidene hydrazines containing three hydroxyl groups in the benzylidene part of their molecules. The prepared compounds were also tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts. IC50 values of these compounds varied in wide range, from an intermediate to no inhibitory effect.
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Keywords: N-(hydroxybenzylidene)-N′-[2,6-dinitro-4-(trifluoromethyl)]phenylhydrazines; radical scavenging activity; DPPH scavenging; GOR scavenging; ABTS scavenging; photosynthetic electron transport N-(hydroxybenzylidene)-N′-[2,6-dinitro-4-(trifluoromethyl)]phenylhydrazines; radical scavenging activity; DPPH scavenging; GOR scavenging; ABTS scavenging; photosynthetic electron transport
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MDPI and ACS Style

Sersen, F.; Gregan, F.; Kotora, P.; Kmetova, J.; Filo, J.; Loos, D.; Gregan, J. Synthesis and Free Radical Scavenging Activity of New Hydroxybenzylidene Hydrazines. Molecules 2017, 22, 894.

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