Molecules (Feb 2024)

Synthesis and Photolysis Properties of a New Chloroquine Photoaffinity Probe

  • Benita Kapuku,
  • D. Scott Bohle

DOI
https://doi.org/10.3390/molecules29051084
Journal volume & issue
Vol. 29, no. 5
p. 1084

Abstract

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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.

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