Design, synthesis and reactivity of C2-symmetric azobenzene-based amino acid-bis(propargyl sulfones)

Abstract

C(2)-symmetric azobenzene-amino acid linked bis(propargyl sulfones) 1 and 2 containing stable E azo moiety have been synthesized. Upon irradiation with long wavelength UV these compounds isomerized to the Z-form, whose thermal reisomerization to the E-isomer slowed down considerably Under basic pH, the compounds showed DNA cleavage in μmolar concentrations with the Z-isomers showing better cleaving efficiency. The difference in cleaving efficiency between the Z and the E-isomer is more than the corresponding pair of sulfones without amino acid linker.