FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W3092238952> ?p ?o ?g. }

• W3092238952 endingPage "4526" @default.
• W3092238952 startingPage "4526" @default.
• W3092238952 abstract "Pharmacological chaperones (PCs) are small compounds able to rescue the activity of mutated lysosomal enzymes when used at subinhibitory concentrations. Nitrogen-containing glycomimetics such as aza- or iminosugars are known to behave as PCs for lysosomal storage disorders (LSDs). As part of our research into lysosomal sphingolipidoses inhibitors and looking in particular for new β-galactosidase inhibitors, we report the synthesis of a series of alkylated azasugars with a relative “all-cis” configuration at the hydroxy/amine-substituted stereocenters. The novel compounds were synthesized from a common carbohydrate-derived piperidinone intermediate 8, through reductive amination or alkylation of the derived alcohol. In addition, the reaction of ketone 8 with several lithium acetylides allowed the stereoselective synthesis of new azasugars alkylated at C-3. The activity of the new compounds towards lysosomal β-galactosidase was negligible, showing that the presence of an alkyl chain in this position is detrimental to inhibitory activity. Interestingly, 9, 10, and 12 behave as good inhibitors of lysosomal β-glucosidase (GCase) (IC50 = 12, 6.4, and 60 µM, respectively). When tested on cell lines bearing the Gaucher mutation, they did not impart any enzyme rescue. However, altogether, the data included in this work give interesting hints for the design of novel inhibitors." @default.
• W3092238952 created "2020-10-15" @default.
• W3092238952 creator A5004665891 @default.
• W3092238952 creator A5026035535 @default.
• W3092238952 creator A5030680362 @default.
• W3092238952 creator A5039610045 @default.
• W3092238952 creator A5077968940 @default.
• W3092238952 creator A5081549372 @default.
• W3092238952 date "2020-10-02" @default.
• W3092238952 modified "2023-10-16" @default.
• W3092238952 title "Synthesis of “All-Cis” Trihydroxypiperidines from a Carbohydrate-Derived Ketone: Hints for the Design of New β-Gal and GCase Inhibitors" @default.
• W3092238952 cites W1489340648 @default.
• W3092238952 cites W1833787853 @default.
• W3092238952 cites W1963514249 @default.
• W3092238952 cites W1970219166 @default.
• W3092238952 cites W1977747792 @default.
• W3092238952 cites W1983928893 @default.
• W3092238952 cites W1986326120 @default.
• W3092238952 cites W1991216094 @default.
• W3092238952 cites W2000365602 @default.
• W3092238952 cites W2004580493 @default.
• W3092238952 cites W2012107327 @default.
• W3092238952 cites W2015352658 @default.
• W3092238952 cites W2022643694 @default.
• W3092238952 cites W2027897295 @default.
• W3092238952 cites W2031348074 @default.
• W3092238952 cites W2037793280 @default.
• W3092238952 cites W2044568919 @default.
• W3092238952 cites W2102440201 @default.
• W3092238952 cites W2116086639 @default.
• W3092238952 cites W2116572569 @default.
• W3092238952 cites W2146692652 @default.
• W3092238952 cites W2147001430 @default.
• W3092238952 cites W2148524443 @default.
• W3092238952 cites W2154054158 @default.
• W3092238952 cites W2161109927 @default.
• W3092238952 cites W2171406737 @default.
• W3092238952 cites W2182495314 @default.
• W3092238952 cites W2310868575 @default.
• W3092238952 cites W2327650204 @default.
• W3092238952 cites W2337279793 @default.
• W3092238952 cites W2480345480 @default.
• W3092238952 cites W2524140589 @default.
• W3092238952 cites W2588840351 @default.
• W3092238952 cites W2760815903 @default.
• W3092238952 cites W2784044092 @default.
• W3092238952 cites W2791576807 @default.
• W3092238952 cites W2792420878 @default.
• W3092238952 cites W2893665080 @default.
• W3092238952 cites W2908654150 @default.
• W3092238952 cites W2913535366 @default.
• W3092238952 cites W2922159284 @default.
• W3092238952 cites W2929961692 @default.
• W3092238952 cites W3007840732 @default.
• W3092238952 cites W3010929988 @default.
• W3092238952 cites W4234505218 @default.
• W3092238952 cites W4238627525 @default.
• W3092238952 doi "https://doi.org/10.3390/molecules25194526" @default.
• W3092238952 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/7582770" @default.
• W3092238952 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33023214" @default.
• W3092238952 hasPublicationYear "2020" @default.
• W3092238952 type Work @default.
• W3092238952 sameAs 3092238952 @default.
• W3092238952 citedByCount "2" @default.
• W3092238952 countsByYear W30922389522022 @default.
• W3092238952 countsByYear W30922389522023 @default.
• W3092238952 crossrefType "journal-article" @default.
• W3092238952 hasAuthorship W3092238952A5004665891 @default.
• W3092238952 hasAuthorship W3092238952A5026035535 @default.
• W3092238952 hasAuthorship W3092238952A5030680362 @default.
• W3092238952 hasAuthorship W3092238952A5039610045 @default.
• W3092238952 hasAuthorship W3092238952A5077968940 @default.
• W3092238952 hasAuthorship W3092238952A5081549372 @default.
• W3092238952 hasBestOaLocation W30922389521 @default.
• W3092238952 hasConcept C131779359 @default.
• W3092238952 hasConcept C134195300 @default.
• W3092238952 hasConcept C146686406 @default.
• W3092238952 hasConcept C161790260 @default.
• W3092238952 hasConcept C164361826 @default.
• W3092238952 hasConcept C178790620 @default.
• W3092238952 hasConcept C181199279 @default.
• W3092238952 hasConcept C181647583 @default.
• W3092238952 hasConcept C185592680 @default.
• W3092238952 hasConcept C198503264 @default.
• W3092238952 hasConcept C21951064 @default.
• W3092238952 hasConcept C2776792218 @default.
• W3092238952 hasConcept C2777738585 @default.
• W3092238952 hasConcept C2778689049 @default.
• W3092238952 hasConcept C2779938440 @default.
• W3092238952 hasConcept C55493867 @default.
• W3092238952 hasConcept C71240020 @default.
• W3092238952 hasConceptScore W3092238952C131779359 @default.
• W3092238952 hasConceptScore W3092238952C134195300 @default.
• W3092238952 hasConceptScore W3092238952C146686406 @default.
• W3092238952 hasConceptScore W3092238952C161790260 @default.
• W3092238952 hasConceptScore W3092238952C164361826 @default.
• W3092238952 hasConceptScore W3092238952C178790620 @default.
• W3092238952 hasConceptScore W3092238952C181199279 @default.

• next