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Synthesis and Biological Evaluation of Fluorinated 3-Phenylcoumarin-7-O-Sulfamate Derivatives as Steroid Sulfatase Inhibitors. 2016

Sebastian Demkowicz, and Mateusz Daśko, and Witold Kozak, and Katarzyna Krawczyk, and Dariusz Witt, and Maciej Masłyk, and Konrad Kubiński, and Janusz Rachon
Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, 80-233, Gdansk, Poland.

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 IC50 values of 0.27 μm (the IC50 value of coumarin-7-O-sulfamate is 3.5 μm, used as a reference).

UI MeSH Term Description Entries
D011485 Protein Binding The process in which substances, either endogenous or exogenous, bind to proteins, peptides, enzymes, protein precursors, or allied compounds. Specific protein-binding measures are often used as assays in diagnostic assessments. Plasma Protein Binding Capacity,Binding, Protein
D003374 Coumarins Synthetic or naturally occurring substances related to coumarin, the delta-lactone of coumarinic acid. 1,2-Benzopyrone Derivatives,1,2-Benzopyrones,Coumarin Derivative,Coumarine,1,2-Benzo-Pyrones,Benzopyran-2-ones,Coumarin Derivatives,Coumarines,1,2 Benzo Pyrones,1,2 Benzopyrone Derivatives,1,2 Benzopyrones,Benzopyran 2 ones,Derivative, Coumarin,Derivatives, 1,2-Benzopyrone,Derivatives, Coumarin
D004791 Enzyme Inhibitors Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Enzyme Inhibitor,Inhibitor, Enzyme,Inhibitors, Enzyme
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D013449 Sulfonamides A group of compounds that contain the structure SO2NH2. Sulfonamide,Sulfonamide Mixture,Sulfonamide Mixtures,Mixture, Sulfonamide,Mixtures, Sulfonamide
D043266 Steryl-Sulfatase An arylsulfatase with high specificity towards sulfated steroids. Defects in this enzyme are the cause of ICHTHYOSIS, X-LINKED. 3 Beta-Hydroxysteroid Sulfate Sulfatase,Arylsulfatase C,Arylsulphatase C,Cholesterol Sulfatase,Cholesterol Sulfate Sulfatase,DHEA Sulfatase,Dehydroepiandrosterone Sulfate Sulfatase,Estrone Sulfate Sulfatase,Estrone Sulfate Sulfohydrolase,Steroid Sulfatase,Steroid Sulfohydrolase,Steroid Sulphatase,Sterol Sulfatase,Sterylsulfatase,3 Beta Hydroxysteroid Sulfate Sulfatase,Steryl Sulfatase,Sulfatase, Cholesterol,Sulfatase, Cholesterol Sulfate,Sulfatase, DHEA,Sulfatase, Dehydroepiandrosterone Sulfate,Sulfatase, Estrone Sulfate,Sulfatase, Steroid,Sulfatase, Sterol,Sulfate Sulfatase, Cholesterol,Sulfate Sulfatase, Dehydroepiandrosterone,Sulfate Sulfatase, Estrone,Sulfate Sulfohydrolase, Estrone,Sulfohydrolase, Estrone Sulfate,Sulfohydrolase, Steroid,Sulphatase, Steroid
D054879 Halogenation Covalent attachment of HALOGENS to other compounds. Bromination,Chlorination,Fluorination,Iodination,Iodation
D020128 Inhibitory Concentration 50 The concentration of a compound needed to reduce population growth of organisms, including eukaryotic cells, by 50% in vitro. Though often expressed to denote in vitro antibacterial activity, it is also used as a benchmark for cytotoxicity to eukaryotic cells in culture. IC50,Concentration 50, Inhibitory
D030562 Databases, Protein Databases containing information about PROTEINS such as AMINO ACID SEQUENCE; PROTEIN CONFORMATION; and other properties. Amino Acid Sequence Databases,Databases, Amino Acid Sequence,Protein Databases,Protein Sequence Databases,SWISS-PROT,Protein Structure Databases,SwissProt,Database, Protein,Database, Protein Sequence,Database, Protein Structure,Databases, Protein Sequence,Databases, Protein Structure,Protein Database,Protein Sequence Database,Protein Structure Database,SWISS PROT,Sequence Database, Protein,Sequence Databases, Protein,Structure Database, Protein,Structure Databases, Protein

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