Indirect and Direct Detection of the 4-(Benzothiazol-2-yl)phenylnitrenium Ion from a Putative Metabolite of a Model Anti-Tumor Drug
| Autor: | Michael Novak, Huo Lei Peng, Samuel C. Brewer, Mrinal Chakraborty, Matthew S. Platz, Kyoung Joo Jin |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Models
Molecular Photolysis Molecular Structure Metabolite Organic Chemistry Photodissociation Phenylnitrenium Antineoplastic Agents Metabolism Biochemistry Article Ion chemistry.chemical_compound Hydrolysis chemistry Anti tumor drug Molecule Organic chemistry Benzothiazoles Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 11:4862-4865 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|