FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2968362493> ?p ?o ?g. }

• W2968362493 endingPage "111614" @default.
• W2968362493 startingPage "111614" @default.
• W2968362493 abstract "Two new piperazinyl-ureido single ring aryl sulfamate-based inhibitor series were designed against the emerging oncology drug target steroid sulfatase (STS), for which there are existing potent steroidal and non-steroidal agents in clinical trials. 4-(Piperazinocarbonyl)aminosulfamates (5–31) were obtained by reacting 4-hydroxyarylamines with phenylchloroformate, subsequent sulfamoylation of the resulting hydroxyarylcarbamates and coupling of the product with 1-substituted piperazines. Pyrimidinyl-piperazinourea sulfamates (35–42) were synthesized by pyrimidine ring closure of 4-Boc-piperazine-1-carboxamidine with 3-(dimethylamino)propenones, deprotection and coupling with the sulfamoylated building block. Target ureidosulfamates 5–31 and 35–42 were evaluated both as STS inhibitors in vitro using a lysate of JEG-3 human placenta choriocarcinoma cell line and in a whole cell assay. SAR conclusions were drawn from both series. In series 35–42 the best inhibitory activity is related to the presence of a benzofuryl on the pyrimidine ring. In series 5–31 the best inhibitory activity was shown by the ureas bearing 4-chlorophenyl, 3,4-dichlorophenyl groups or aliphatic chains at the piperazino 4-nitrogen displaying IC50 in the 33–94 nM concentration range. Final optimization to the low nanomolar level was achieved through substitution of the arylsulfamate ring with halogens. Four halogenated arylsulfamates of high potency were achieved and two of these 19 and 20 had IC50 values of 5.1 and 8.8 nM respectively and are attractive for potential in vivo evaluation and further development. We demonstrate the optimization of this new series to low nanomolar potency, employing fluorine substitution, providing potent membrane permeant inhibitors with further development potential indicating piperazinyl-ureido aryl sulfamate derivatives as an attractive new class of STS inhibitors." @default.
• W2968362493 created "2019-08-22" @default.
• W2968362493 creator A5004708346 @default.
• W2968362493 creator A5023339313 @default.
• W2968362493 creator A5042341003 @default.
• W2968362493 creator A5048329837 @default.
• W2968362493 creator A5054953431 @default.
• W2968362493 creator A5056175643 @default.
• W2968362493 creator A5082393921 @default.
• W2968362493 date "2019-11-01" @default.
• W2968362493 modified "2023-10-16" @default.
• W2968362493 title "Synthesis and in vitro evaluation of piperazinyl-ureido sulfamates as steroid sulfatase inhibitors" @default.
• W2968362493 cites W1494423816 @default.
• W2968362493 cites W1964485062 @default.
• W2968362493 cites W1972493915 @default.
• W2968362493 cites W1973813358 @default.
• W2968362493 cites W1974752167 @default.
• W2968362493 cites W1990763118 @default.
• W2968362493 cites W1991080894 @default.
• W2968362493 cites W2001070076 @default.
• W2968362493 cites W2014536534 @default.
• W2968362493 cites W2020948060 @default.
• W2968362493 cites W2029154177 @default.
• W2968362493 cites W2051917527 @default.
• W2968362493 cites W2052933595 @default.
• W2968362493 cites W2062299665 @default.
• W2968362493 cites W2066093944 @default.
• W2968362493 cites W2072214192 @default.
• W2968362493 cites W2087150071 @default.
• W2968362493 cites W2087174112 @default.
• W2968362493 cites W2088677748 @default.
• W2968362493 cites W2092309725 @default.
• W2968362493 cites W2098841434 @default.
• W2968362493 cites W2124246726 @default.
• W2968362493 cites W2127285450 @default.
• W2968362493 cites W2128455963 @default.
• W2968362493 cites W2128828790 @default.
• W2968362493 cites W2136207509 @default.
• W2968362493 cites W2163359570 @default.
• W2968362493 cites W2180096718 @default.
• W2968362493 cites W2280153690 @default.
• W2968362493 cites W2337352499 @default.
• W2968362493 cites W2566197758 @default.
• W2968362493 cites W2624837801 @default.
• W2968362493 cites W2744817126 @default.
• W2968362493 cites W276536374 @default.
• W2968362493 cites W2795504821 @default.
• W2968362493 cites W2891850968 @default.
• W2968362493 cites W2944748061 @default.
• W2968362493 cites W2951638273 @default.
• W2968362493 cites W832523408 @default.
• W2968362493 doi "https://doi.org/10.1016/j.ejmech.2019.111614" @default.
• W2968362493 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/31422224" @default.
• W2968362493 hasPublicationYear "2019" @default.
• W2968362493 type Work @default.
• W2968362493 sameAs 2968362493 @default.
• W2968362493 citedByCount "10" @default.
• W2968362493 countsByYear W29683624932020 @default.
• W2968362493 countsByYear W29683624932021 @default.
• W2968362493 countsByYear W29683624932022 @default.
• W2968362493 crossrefType "journal-article" @default.
• W2968362493 hasAuthorship W2968362493A5004708346 @default.
• W2968362493 hasAuthorship W2968362493A5023339313 @default.
• W2968362493 hasAuthorship W2968362493A5042341003 @default.
• W2968362493 hasAuthorship W2968362493A5048329837 @default.
• W2968362493 hasAuthorship W2968362493A5054953431 @default.
• W2968362493 hasAuthorship W2968362493A5056175643 @default.
• W2968362493 hasAuthorship W2968362493A5082393921 @default.
• W2968362493 hasBestOaLocation W29683624932 @default.
• W2968362493 hasConcept C150903083 @default.
• W2968362493 hasConcept C178790620 @default.
• W2968362493 hasConcept C185592680 @default.
• W2968362493 hasConcept C202751555 @default.
• W2968362493 hasConcept C207001950 @default.
• W2968362493 hasConcept C2777752497 @default.
• W2968362493 hasConcept C2778090324 @default.
• W2968362493 hasConcept C2779321679 @default.
• W2968362493 hasConcept C2780263894 @default.
• W2968362493 hasConcept C2780378348 @default.
• W2968362493 hasConcept C2780902042 @default.
• W2968362493 hasConcept C2781056017 @default.
• W2968362493 hasConcept C2781076698 @default.
• W2968362493 hasConcept C55493867 @default.
• W2968362493 hasConcept C57992300 @default.
• W2968362493 hasConcept C71240020 @default.
• W2968362493 hasConcept C71315377 @default.
• W2968362493 hasConcept C86803240 @default.
• W2968362493 hasConceptScore W2968362493C150903083 @default.
• W2968362493 hasConceptScore W2968362493C178790620 @default.
• W2968362493 hasConceptScore W2968362493C185592680 @default.
• W2968362493 hasConceptScore W2968362493C202751555 @default.
• W2968362493 hasConceptScore W2968362493C207001950 @default.
• W2968362493 hasConceptScore W2968362493C2777752497 @default.
• W2968362493 hasConceptScore W2968362493C2778090324 @default.
• W2968362493 hasConceptScore W2968362493C2779321679 @default.
• W2968362493 hasConceptScore W2968362493C2780263894 @default.
• W2968362493 hasConceptScore W2968362493C2780378348 @default.
• W2968362493 hasConceptScore W2968362493C2780902042 @default.

• next