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

doi:10.1021/ol901959z

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 journal › Article › peer-review

25 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 λ_max 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 language	English (US)
Pages (from-to)	4862-4865
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	21
DOIs	https://doi.org/10.1021/ol901959z
State	Published - Nov 5 2009
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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

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.",

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T1 - Indirect and direct detection of the 4-(benzothiazol-2-yl)phenylnitrenium ion from a putative metabolite of a model anti-tumor drug

AU - Chakraborty, Mrinal

AU - Jin, Kyoung Joo

AU - Brewer, Samuel C.

AU - Peng, Huo Lei

AU - Platz, Matthew S.

AU - Novak, Michael

PY - 2009/11/5

Y1 - 2009/11/5

N2 - 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.

AB - 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.

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ER -

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

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