School of Chemistry, National University of Ireland Galway, University Road, H91 TK33 Galway, Ireland.
Department of Chemistry, University of Cyprus, P.O. Box 20537, Nicosia 1678, Cyprus.
Molecules. 2019 Jan 14;24(2):282. doi: 10.3390/molecules24020282.
7-Oxo-1,2,4-benzotriazines (benzo[1,2,4]triazin-7-ones) are reversible thioredoxin reductase inhibitors that exhibit very strong correlations to pleurotin. In this article, we provide the first synthesis of fluorinated derivatives. Fluorination using Selectfluor of benzo[1,2,4]triazin-7-ones occurs regioselectively and in high yield at the enamine-activated position. This electron N-lone pair activation overrides the activation/deactivation effects of some other substituents. The reaction time was significantly reduced with the use of microwave irradiation at 120 °C and 7 bar. The cytotoxicity and cyclic voltammetry measurements for 8-fluoro-1,3-diphenylbenzo[][1,2,4]triazin-7(1)-one () are presented and compared with its synthetic precursor, 1,3-diphenylbenzo[][1,2,4]triazin-7(1)-one ().
7-氧代-1,2,4-苯并三嗪（苯并[1,2,4]三嗪-7-酮）是一种可逆的硫氧还蛋白还原酶抑制剂，与 pleurotin 具有很强的相关性。在本文中，我们首次合成了氟化衍生物。使用 Selectfluor 对苯并[1,2,4]三嗪-7-酮进行氟化反应，在烯胺活化位置具有区域选择性和高产率。这种电子 N-孤对的活化克服了其他一些取代基的活化/失活效应。使用微波辐射在 120°C 和 7 巴的条件下，反应时间显著缩短。还介绍了 8-氟-1,3-二苯基苯并[][1,2,4]三嗪-7(1)-酮（）的细胞毒性和循环伏安法测量结果，并与它的合成前体 1,3-二苯基苯并[][1,2,4]三嗪-7(1)-酮（）进行了比较。
