The design, synthesis, and biochemical evaluation of derivatives of biphenyl sulfamate-based compounds as novel inhibitors of estrone sulfatase

We report the initial results of our study into the use of a potential transition state (TS) of the reaction catalyzed by the enzyme estrone sulfatase (ES) in the design of a series of simple 4 ′- O-sulfamoyl-4-biphenyl-based compounds as novel inhibitors of ES. The results of the study show that th...

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Bibliographic Details
Published in:Biochemical and biophysical research communications 2002-05, Vol.294 (1), p.180-183
Main Authors: Ahmed, Sabbir, James, Karen, Owen, Caroline P
Format: Article
Language:English
Subjects:
Catalysis
Coumarins - chemistry
Coumarins - pharmacology
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Estrone - analogs & derivatives
Estrone - chemistry
Estrone - pharmacology
Models, Chemical
Models, Molecular
Sulfatases - antagonists & inhibitors
Sulfonamides - chemistry
Sulfonamides - pharmacology
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Summary:We report the initial results of our study into the use of a potential transition state (TS) of the reaction catalyzed by the enzyme estrone sulfatase (ES) in the design of a series of simple 4 ′- O-sulfamoyl-4-biphenyl-based compounds as novel inhibitors of ES. The results of the study show that these compounds are: potent inhibitors, possessing greater inhibitory activity than 4-methylcoumarin-7- O-sulfamate (COUMATE); weaker inhibitors than the tricyclic derivative of COUMATE, namely 667-COUMATE and the steroidal inhibitor estrone-3- O-sulfamate (EMATE), and irreversible inhibitors of ES.
ISSN:0006-291X
1090-2104
DOI:10.1016/S0006-291X(02)00444-8