Synthesis and Free Radical Scavenging Activity of New Hydroxybenzylidene Hydrazines
Frantisek Sersen,
Fridrich Gregan,
Peter Kotora,
Jarmila Kmetova,
Juraj Filo,
Dusan Loos,
Juraj Gregan
Affiliations
Frantisek Sersen
Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Ilkovicova 6, 842 15 Bratislava, Slovakia
Fridrich Gregan
Department of Chemistry, Faculty of Natural Sciences, Matej Bell University, Tajovskeho 40, 974 01 Banska Bystrica, Slovakia
Peter Kotora
Institute of Process Engineering, Faculty of Mechanical Engineering, Slovak University of Technology in Bratislava, Namestie slobody 17, 812 31 Bratislava, Slovakia
Jarmila Kmetova
Department of Chemistry, Faculty of Natural Sciences, Matej Bell University, Tajovskeho 40, 974 01 Banska Bystrica, Slovakia
Juraj Filo
Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Ilkovicova 6, 842 15 Bratislava, Slovakia
Dusan Loos
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Ilkovicova 6, 842 15 Bratislava, Slovakia
Juraj Gregan
Department of Genetics, Faculty of Natural Sciences, Comenius University in Bratislava, Ilkovicova 6, 842 15 Bratislava, Slovakia
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.
