Sersen Frantisek, Gregan Fridrich, Kotora Peter, Kmetova Jarmila, Filo Juraj, Loos Dusan, Gregan Juraj
Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Ilkovicova 6, 842 15 Bratislava, Slovakia.
Department of Chemistry, Faculty of Natural Sciences, Matej Bell University, Tajovskeho 40, 974 01 Banska Bystrica, Slovakia.
Molecules. 2017 May 29;22(6):894. doi: 10.3390/molecules22060894.
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.
羟基苯亚甲基肼类化合物具有广泛的生物活性。在此，我们报道了9种新型N-(羟基苯亚甲基)-N'-[2,6-二硝基-4-(三氟甲基)]苯基肼的合成及其自由基清除活性。这些化合物的化学结构通过1H-NMR、13C-NMR、19F-NMR、红外光谱、液相色谱-质谱联用以及元素分析得以确证。对所制备的化合物进行了清除2,2-二苯基-1-苦基肼自由基（DPPH）、加尔文氧自由基（GOR）以及2,2'-联氮-双-(3-乙基苯并噻唑啉-6-磺酸)自由基（ABTS）的活性测试。以SC50值表示的这些化合物的自由基清除活性在很宽的范围内变化，从具有强自由基清除作用到无清除作用。最有效的自由基清除剂是在其分子的苯亚甲基部分含有三个羟基的羟基苯亚甲基肼。还对所制备的化合物抑制菠菜叶绿体光合电子传递的活性进行了测试。这些化合物的IC50值在很宽的范围内变化，从具有中等抑制作用到无抑制作用。
