Antitumor Benzothiazoles. 8. Synthesis, Metabolic Formation, and Biological Properties of the C- and N-Oxidation Products of Antitumor 2-(4-Aminophenyl)benzothiazoles

2-(4-Aminophenyl)benzothiazoles 1 and their N-acetylated forms have been converted to C- and N-hydroxylated derivatives to investigate the role of metabolic oxidation in the mode of action of this series of compounds. 2-(4-Amino-3-methylphenyl)benzothiazole (1a, DF 203, NSC 674495) is a novel and po...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1999-10, Vol.42 (20), p.4172-4184
Main Authors: Kashiyama, Eiji, Hutchinson, Ian, Chua, Mei-Sze, Stinson, Sherman F, Phillips, Lawrence R, Kaur, Gurmeet, Sausville, Edward A, Bradshaw, Tracey D, Westwell, Andrew D, Stevens, Malcolm F. G
Format: Article
Language:English
Subjects:
Aniline Compounds - chemical synthesis
Aniline Compounds - chemistry
Aniline Compounds - metabolism
Aniline Compounds - pharmacology
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - metabolism
Antineoplastic Agents - pharmacology
Benzothiazoles
Biological and medical sciences
Culture Media
Drug Screening Assays, Antitumor
General aspects
Humans
Medical sciences
Oxidation-Reduction
Pharmacology. Drug treatments
Radioligand Assay
Structure-Activity Relationship
Thiazoles - chemical synthesis
Thiazoles - chemistry
Thiazoles - metabolism
Thiazoles - pharmacology
Tumor Cells, Cultured
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Summary:2-(4-Aminophenyl)benzothiazoles 1 and their N-acetylated forms have been converted to C- and N-hydroxylated derivatives to investigate the role of metabolic oxidation in the mode of action of this series of compounds. 2-(4-Amino-3-methylphenyl)benzothiazole (1a, DF 203, NSC 674495) is a novel and potent antitumor agent with selective growth inhibitory properties against human cancer cell lines. Very low IC50 values (
ISSN:0022-2623
1520-4804
DOI:10.1021/jm990104o