FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W1973497184> ?p ?o ?g. }

• W1973497184 endingPage "2548" @default.
• W1973497184 startingPage "2541" @default.
• W1973497184 abstract "Eight new C5-substituted derivatives of the potential atypical antipsychotic agent 5-methoxy-2-[N-(2-benzamidoethyl)-N-n-propylamino]tetralin (5-OMe-BPAT, 1) have been prepared by chemical conversion of the 5-trifluoromethylsulfonyloxy (triflate) analogue 4 via various Stille-type cross-couplings, a Heck reaction, and an amidation in moderate to good yields. The 5-acetyl, 5-cyano, 5-methyl, 5-(2-furyl), 5-phenyl, methyl 5-carboxylate, and the 5-carboxamido analogues Scheme 1, Scheme 2 thus obtained, the previously disclosed 5-methoxy, 5-hydroxy, and 5-unsubstituted analogues 1–3, and the 5-triflate analogue 4 were evaluated for their ability to compete for [3H]-spiperone binding to rat striatal membranes containing dopamine D2 receptors, and their ability to compete for [3H]-8-OH-DPAT binding to rat frontal cortex membranes containing serotonin 5-HT1A receptors in vitro. Compounds Scheme 1, Scheme 2 displayed weak to high affinities for dopamine D2 receptors, with Ki-values ranging from 550 nM for the 5-carboxamido analogue to 4.9 nM for the 5-hydroxy analogue. The relative affinities of the 5-methoxy, 5-hydroxy, and 5-unsubstituted analogues suggested that these compounds may bind to the same site and in a similar way as the 5-oxygenated DPATs, with the 5-methoxy substituent of 1 functioning as a hydrogen bond acceptor. The serotonin 5-HT1A receptor tolerated more structural diversity at the C5-position of 1, as revealed by the higher Ki-values of Scheme 1, Scheme 2, which ranged from 60 nM for the 5-carboxamido analogue to 1.0 nM for the 5-unsubstituted analogue. Partial least-squares (PLS) analysis of a set of 24 molecular descriptors, generated for each analogue, revealed no significant correlation between the dopamine D2 receptor affinities of Scheme 1, Scheme 2 and their molecular properties, supporting the view that they may have different binding modes at this receptor subtype. A PLS model with moderate predictability (Q2=0.49) could be derived for the serotonin 5-HT1A receptor affinities of Scheme 1, Scheme 2. According to the model, a relatively lipophilic, nonpolar C5-substituent should be optimal for a high affinity at this receptor subtype." @default.
• W1973497184 created "2016-06-24" @default.
• W1973497184 creator A5014561284 @default.
• W1973497184 creator A5016071108 @default.
• W1973497184 creator A5030118197 @default.
• W1973497184 creator A5043248014 @default.
• W1973497184 creator A5063361719 @default.
• W1973497184 date "1999-11-01" @default.
• W1973497184 modified "2023-10-17" @default.
• W1973497184 title "C5-Substituted Derivatives of 5-OMe-BPAT: Synthesis and Interactions with Dopamine D2 and Serotonin 5-HT1A Receptors" @default.
• W1973497184 cites W1523570821 @default.
• W1973497184 cites W1964971292 @default.
• W1973497184 cites W1965395049 @default.
• W1973497184 cites W1965419059 @default.
• W1973497184 cites W1966377499 @default.
• W1973497184 cites W1974482128 @default.
• W1973497184 cites W1981064572 @default.
• W1973497184 cites W1981628074 @default.
• W1973497184 cites W1988062492 @default.
• W1973497184 cites W1990640560 @default.
• W1973497184 cites W1991427866 @default.
• W1973497184 cites W1992281684 @default.
• W1973497184 cites W1992840579 @default.
• W1973497184 cites W1997448807 @default.
• W1973497184 cites W2022209208 @default.
• W1973497184 cites W2022486547 @default.
• W1973497184 cites W2022875984 @default.
• W1973497184 cites W2029746418 @default.
• W1973497184 cites W2051527605 @default.
• W1973497184 cites W2051566866 @default.
• W1973497184 cites W2052594240 @default.
• W1973497184 cites W2058393017 @default.
• W1973497184 cites W2062375658 @default.
• W1973497184 cites W2066773748 @default.
• W1973497184 cites W2069444705 @default.
• W1973497184 cites W2074631079 @default.
• W1973497184 cites W2080174461 @default.
• W1973497184 cites W2084481837 @default.
• W1973497184 cites W2106322132 @default.
• W1973497184 cites W2120630627 @default.
• W1973497184 cites W2137417595 @default.
• W1973497184 cites W2138067285 @default.
• W1973497184 cites W2158863190 @default.
• W1973497184 cites W2950509508 @default.
• W1973497184 doi "https://doi.org/10.1016/s0968-0896(99)00196-0" @default.
• W1973497184 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/10632064" @default.
• W1973497184 hasPublicationYear "1999" @default.
• W1973497184 type Work @default.
• W1973497184 sameAs 1973497184 @default.
• W1973497184 citedByCount "5" @default.
• W1973497184 crossrefType "journal-article" @default.
• W1973497184 hasAuthorship W1973497184A5014561284 @default.
• W1973497184 hasAuthorship W1973497184A5016071108 @default.
• W1973497184 hasAuthorship W1973497184A5030118197 @default.
• W1973497184 hasAuthorship W1973497184A5043248014 @default.
• W1973497184 hasAuthorship W1973497184A5063361719 @default.
• W1973497184 hasConcept C120069818 @default.
• W1973497184 hasConcept C161790260 @default.
• W1973497184 hasConcept C169760540 @default.
• W1973497184 hasConcept C170493617 @default.
• W1973497184 hasConcept C185592680 @default.
• W1973497184 hasConcept C21774173 @default.
• W1973497184 hasConcept C2775864247 @default.
• W1973497184 hasConcept C44208683 @default.
• W1973497184 hasConcept C513476851 @default.
• W1973497184 hasConcept C53910766 @default.
• W1973497184 hasConcept C55493867 @default.
• W1973497184 hasConcept C71240020 @default.
• W1973497184 hasConcept C86803240 @default.
• W1973497184 hasConceptScore W1973497184C120069818 @default.
• W1973497184 hasConceptScore W1973497184C161790260 @default.
• W1973497184 hasConceptScore W1973497184C169760540 @default.
• W1973497184 hasConceptScore W1973497184C170493617 @default.
• W1973497184 hasConceptScore W1973497184C185592680 @default.
• W1973497184 hasConceptScore W1973497184C21774173 @default.
• W1973497184 hasConceptScore W1973497184C2775864247 @default.
• W1973497184 hasConceptScore W1973497184C44208683 @default.
• W1973497184 hasConceptScore W1973497184C513476851 @default.
• W1973497184 hasConceptScore W1973497184C53910766 @default.
• W1973497184 hasConceptScore W1973497184C55493867 @default.
• W1973497184 hasConceptScore W1973497184C71240020 @default.
• W1973497184 hasConceptScore W1973497184C86803240 @default.
• W1973497184 hasIssue "11" @default.
• W1973497184 hasLocation W19734971841 @default.
• W1973497184 hasLocation W19734971842 @default.
• W1973497184 hasOpenAccess W1973497184 @default.
• W1973497184 hasPrimaryLocation W19734971841 @default.
• W1973497184 hasRelatedWork W1976805986 @default.
• W1973497184 hasRelatedWork W2058091174 @default.
• W1973497184 hasRelatedWork W2156790153 @default.
• W1973497184 hasRelatedWork W2162230839 @default.
• W1973497184 hasRelatedWork W2419529664 @default.
• W1973497184 hasRelatedWork W3099606857 @default.
• W1973497184 hasRelatedWork W3200989062 @default.
• W1973497184 hasRelatedWork W4206347286 @default.
• W1973497184 hasRelatedWork W4290155861 @default.
• W1973497184 hasRelatedWork W4299615109 @default.
• W1973497184 hasVolume "7" @default.

• next