Kapuku Benita, Bohle D Scott
Department of Chemistry, McGill University, 801 Sherbrooke St. W., Montreal, QC H3A 0B8, Canada.
Molecules. 2024 Feb 29;29(5):1084. doi: 10.3390/molecules29051084.
A new chloroquine-derived photoaffinity probe has been prepared by a convergent synthesis from derivative of 4,7-dichloroquinoline and N1,N1-diethyl-N4-methylpentane. The features of this probe are a unique 3-azido photolabel, the pyridine ring of the quinoline, and the presence of a secondary amine at the 4-position of the quinoline. These features, particularly the 4-amino methylation, prevent triazole formation through combination of the 3-azide and the 4-amine. This undergoes facile cleavage with exposure to a medium-pressure mercury lamp with a 254 nm excitation wavelength. Trapping of the nitrene byproduct is accomplished with its reaction with N-phenylmaleimide as its cycloazidation product. The structure of a ring-opened DBU amine has been structurally characterized.
一种新的氯喹衍生光亲和探针通过4,7-二氯喹啉衍生物与N1,N1-二乙基-N4-甲基戊烷的汇聚合成法制备而成。该探针的特点是具有独特的3-叠氮基光标记、喹啉的吡啶环以及喹啉4位上存在仲胺。这些特点，尤其是4-氨基甲基化，可防止3-叠氮基与4-胺结合形成三唑。该探针在暴露于激发波长为254 nm的中压汞灯时会发生容易的裂解。通过与N-苯基马来酰亚胺反应作为其环叠氮化产物来捕获氮烯副产物。已对开环DBU胺的结构进行了表征。
