FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2894791214> ?p ?o ?g. }

• W2894791214 endingPage "316" @default.
• W2894791214 startingPage "307" @default.
• W2894791214 abstract "The conjugated system of cinnamic acid, α-substituted with a phosphonoalkyl residue, was previously validated as a scaffold that provided one of the most potent organophosphorus inhibitors of bacterial urease. Following the idea of using Morita-Baylis-Hillman adducts to introduce the terminal phosphonic side chain functionality to the α,β-unsaturated system, we currently report the synthesis and activity of an extended series of compounds. Cinnamates modified with 3-phosphonopropyl and 4-phosphonobutyl side chains were obtained in a convenient two-step procedure, which involved Pd-mediated transformations of the Morita-Baylis-Hillman bromides as the key substrates. The introduction of a terminal alkenyl fragment, which was achieved by Stille coupling with stannanes, was followed by a tandem C-P bond formation/oxidation process. A submicromolar ligand of Sporosarcina pasteurii urease (Ki = 0.509 μM) was identified among the active molecules. In addition, inhibitors of Proteus mirabilis urease affected bacterial growth at the micromolar level. Based on the structure-activity relationship and the mechanism of inhibition, we suggest a nontypical mixed mode of action for the slow binding compounds. We presume that the molecular distance between the phosphonic group and the backbone double bond allows a dual activity: complexation of the acidic group with nickel ions and Michael addition of a cysteine forming the active site lid." @default.
• W2894791214 created "2018-10-12" @default.
• W2894791214 creator A5028966759 @default.
• W2894791214 creator A5061135367 @default.
• W2894791214 creator A5063684833 @default.
• W2894791214 creator A5079265593 @default.
• W2894791214 creator A5088642666 @default.
• W2894791214 date "2018-11-01" @default.
• W2894791214 modified "2023-09-25" @default.
• W2894791214 title "Structural exploration of cinnamate-based phosphonic acids as inhibitors of bacterial ureases" @default.
• W2894791214 cites W111798076 @default.
• W2894791214 cites W1899069604 @default.
• W2894791214 cites W1971705557 @default.
• W2894791214 cites W1982700422 @default.
• W2894791214 cites W1985729069 @default.
• W2894791214 cites W2007748264 @default.
• W2894791214 cites W2007785330 @default.
• W2894791214 cites W2019701320 @default.
• W2894791214 cites W2021553112 @default.
• W2894791214 cites W2032294371 @default.
• W2894791214 cites W2066442269 @default.
• W2894791214 cites W2067785467 @default.
• W2894791214 cites W2067998161 @default.
• W2894791214 cites W2077938400 @default.
• W2894791214 cites W2081047141 @default.
• W2894791214 cites W2081289996 @default.
• W2894791214 cites W2092915584 @default.
• W2894791214 cites W2095041765 @default.
• W2894791214 cites W2108317022 @default.
• W2894791214 cites W2109987434 @default.
• W2894791214 cites W2114594973 @default.
• W2894791214 cites W2139787143 @default.
• W2894791214 cites W2142312912 @default.
• W2894791214 cites W2153045427 @default.
• W2894791214 cites W2153165213 @default.
• W2894791214 cites W2158123709 @default.
• W2894791214 cites W2174014422 @default.
• W2894791214 cites W2178889737 @default.
• W2894791214 cites W2216063091 @default.
• W2894791214 cites W2314103805 @default.
• W2894791214 cites W2316005451 @default.
• W2894791214 cites W2318066473 @default.
• W2894791214 cites W2322250019 @default.
• W2894791214 cites W2331780316 @default.
• W2894791214 cites W2510927590 @default.
• W2894791214 cites W2559675363 @default.
• W2894791214 cites W2587967902 @default.
• W2894791214 cites W2598343444 @default.
• W2894791214 cites W2800182274 @default.
• W2894791214 cites W2803103828 @default.
• W2894791214 cites W2810347648 @default.
• W2894791214 cites W2884567349 @default.
• W2894791214 cites W2949247294 @default.
• W2894791214 cites W2949904403 @default.
• W2894791214 cites W2951602907 @default.
• W2894791214 cites W2951732877 @default.
• W2894791214 cites W4239747192 @default.
• W2894791214 doi "https://doi.org/10.1016/j.ejmech.2018.09.074" @default.
• W2894791214 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30300843" @default.
• W2894791214 hasPublicationYear "2018" @default.
• W2894791214 type Work @default.
• W2894791214 sameAs 2894791214 @default.
• W2894791214 citedByCount "13" @default.
• W2894791214 countsByYear W28947912142019 @default.
• W2894791214 countsByYear W28947912142020 @default.
• W2894791214 countsByYear W28947912142021 @default.
• W2894791214 countsByYear W28947912142022 @default.
• W2894791214 countsByYear W28947912142023 @default.
• W2894791214 crossrefType "journal-article" @default.
• W2894791214 hasAuthorship W2894791214A5028966759 @default.
• W2894791214 hasAuthorship W2894791214A5061135367 @default.
• W2894791214 hasAuthorship W2894791214A5063684833 @default.
• W2894791214 hasAuthorship W2894791214A5079265593 @default.
• W2894791214 hasAuthorship W2894791214A5088642666 @default.
• W2894791214 hasConcept C108204754 @default.
• W2894791214 hasConcept C112613896 @default.
• W2894791214 hasConcept C116569031 @default.
• W2894791214 hasConcept C170493617 @default.
• W2894791214 hasConcept C178790620 @default.
• W2894791214 hasConcept C181199279 @default.
• W2894791214 hasConcept C185592680 @default.
• W2894791214 hasConcept C204921945 @default.
• W2894791214 hasConcept C21951064 @default.
• W2894791214 hasConcept C2779201268 @default.
• W2894791214 hasConcept C2779521917 @default.
• W2894791214 hasConcept C41183919 @default.
• W2894791214 hasConcept C521977710 @default.
• W2894791214 hasConcept C55493867 @default.
• W2894791214 hasConcept C71240020 @default.
• W2894791214 hasConceptScore W2894791214C108204754 @default.
• W2894791214 hasConceptScore W2894791214C112613896 @default.
• W2894791214 hasConceptScore W2894791214C116569031 @default.
• W2894791214 hasConceptScore W2894791214C170493617 @default.
• W2894791214 hasConceptScore W2894791214C178790620 @default.
• W2894791214 hasConceptScore W2894791214C181199279 @default.
• W2894791214 hasConceptScore W2894791214C185592680 @default.
• W2894791214 hasConceptScore W2894791214C204921945 @default.
• W2894791214 hasConceptScore W2894791214C21951064 @default.

• next