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Synthesis and Biological Evaluation of Fluorinated 3‐Phenylcoumarin‐7‐ O ‐Sulfamate Derivatives as Steroid Sulfatase Inhibitors
Author(s) -
Demkowicz Sebastian,
Daśko Mateusz,
Kozak Witold,
Krawczyk Katarzyna,
Witt Dariusz,
Masłyk Maciej,
Kubiński Konrad,
Rachon Janusz
Publication year - 2016
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12652
Subject(s) - steroid sulfatase , steroid , coumarin , chemistry , ic50 , potency , enzyme , stereochemistry , sulfatase , biochemistry , in vitro , organic chemistry , hormone
In the present work, we report the initial results of our study on a series of 3‐phenylcoumarin sulfamate‐based compounds containing C‐F bonds as novel inhibitors of steroid sulfatase. The new compounds are potent steroid sulfatase inhibitors, possessing more than 10 times higher inhibitory potency than coumarin‐7‐ O ‐sulfamate. In the course of our investigation, compounds 2b and 2c demonstrated the highest inhibitory effect on the enzymatic steroid sulfatase assay; both had IC 50 values of 0.27 μ m (the IC 50 value of coumarin‐7‐ O ‐sulfamate is 3.5 μ m , used as a reference).