Indirect and direct detection of the 4-(benzothiazol-2-yl)phenylnitrenium ion from a putative metabolite of a model anti-tumor drug.
2-(4-Aminophenyl)benzothiazoles related to 1 are potentially important pharmaceuticals. Metabolism apparently involves oxidation and esterification to 3. In water, hydrolysis and photolysis of 3 generates the nitrenium ion 4 that can be detected indirectly by N(3)(-) trapping and directly by UV-vis spectroscopy following laser flash photolysis. The transient, with lambda(max) 570 nm, and a lifetime of 530 ns, reacts with N(3)(-) at a diffusion-controlled rate and generates the quinol 6 by reaction with water.
Department of Chemistry and Biochemistry, Miami University, Oxford, Ohio 45056, USA.
Mrinal
M
Chakraborty
Kyoung Joo
KJ
Jin
Samuel C
SC
Brewer
Huo-Lei
HL
Peng
Matthew S
MS
Platz
Michael
M
Novak
D000970:Antineoplastic Agents / Q000032:analysis* / Q000737:chemistry; D052160:Benzothiazoles / Q000032:analysis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010782:Photolysis
C111133:2-(4-aminophenyl)benzothiazole; C545618:4-(benzothiazol-2-yl)phenylnitrenium; D000970:Antineoplastic Agents; D052160:Benzothiazoles