Department of Chemistry and Biochemistry , Kent State University , Kent , Ohio 44242 , United States.
School of Science , Auckland University of Technology , Auckland 1142 , New Zealand.
Org Lett. 2019 Feb 15;21(4):1054-1057. doi: 10.1021/acs.orglett.8b04099. Epub 2019 Jan 29.
The design and synthesis of a photoactivatable HNO donor incorporating the (6-hydroxynaphthalen-2-yl)methyl (6,2-HNM) photocage coupled to the trifluoromethanesulfonamidoxy analogue of the well-established HNO generator Piloty's acid is described. The photoactive HNO donor stoichiometrically generates HNO (∼98%) at neutral pH conditions, and evidence for concerted C-O and N-S bond cleavage was obtained. The methanesulfonamidoxy analogue primarily undergoes undesired N-O bond cleavage.
描述了一种光活化的 HNO 供体的设计和合成,该供体结合了(6-羟基萘-2-基)甲基(6,2-HNM)光笼,与经过充分验证的 HNO 发生器 Piloty 酸的三氟甲磺酰胺氧基类似物相连。在中性 pH 条件下,光活性 HNO 供体以化学计量比生成 HNO(∼98%),并获得了协同 C-O 和 N-S 键断裂的证据。甲磺酰胺氧基类似物主要经历了不需要的 N-O 键断裂。