Synthesis and reactivity of azobenzene-based bispropargyl sulfones: interesting comparison between cyclic and acyclic systems.
Azobenzene-based bispropargyl bissulfone 3 containing stable E-azo moiety has been synthesized. Upon irradiation with long wavelength UV it isomerized to the Z-form 4, which can be thermally reisomerized to the E-isomer. Reactivity towards isomerization to the allenic system as well as DNA-cleaving efficiency under basic conditions was found to be significantly lower as compared to the previously synthesized cyclic sulfones 1 and 2. This lowering of reactivity can be explained in terms of low conversion to the allenic form and hence the lower extent of alkylation of DNA-bases, the only possible DNA-cleavage pathway for 3 and 4.
Mitra
Debarati
D
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
Kar
Moumita
M
Pal
Rhitankar
R
Basak
Amit
A
D000970:Antineoplastic Agents / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D053837:DNA Cleavage; D015394:Molecular Structure; D013450:Sulfones / Q000737:chemistry*
D000970:Antineoplastic Agents; D001391:Azo Compounds; D013450:Sulfones; C009850:azobenzene