Indirect and direct detection of the 4-(benzothiazol-2-yl)phenylnitrenium ion from a putative metabolite of a model anti-tumor drug

Mrinal Chakraborty, Kyoung Joo Jin, Samuel C. Brewer, Huo Lei Peng, Matthew S. Platz, Michael Novak

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

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 N3- trapping and directly by UV-vis spectroscopy following laser flash photolysis. The transient, with λmax 570 nm, and a lifetime of 530 ns, reacts with N 3- at a diffusioncontrolled rate and generates the quinol 6 by reaction with water.

Original languageEnglish (US)
Pages (from-to)4862-4865
Number of pages4
JournalOrganic Letters
Volume11
Issue number21
DOIs
StatePublished - Nov 5 2009

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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