1
40
2
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Text
A resource consisting primarily of words for reading. Examples include books, letters, dissertations, poems, newspapers, articles, archives of mailing lists. Note that facsimiles or images of texts are still of the genre Text.
URL Address
<a href="http://doi.org/10.1016/j.molstruc.2013.04.030" target="_blank" rel="noreferrer noopener">http://doi.org/10.1016/j.molstruc.2013.04.030</a>
Rights
Article information provided for research and reference use only. All rights are retained by the journal listed under publisher and/or the creator(s).
Pages
86-94
Volume
1045
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Dublin Core
The Dublin Core metadata element set is common to all Omeka records, including items, files, and collections. For more information see, http://dublincore.org/documents/dces/.
Title
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Triquinane scaffolds: Shape and geometry as a function of saturation and bridgehead groups
Publisher
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Journal of Molecular Structure
Date
A point or period of time associated with an event in the lifecycle of the resource
2013
2013-08
Subject
The topic of the resource
amines; blocker; Chemistry; Crystal structure; derivatives; L-type calcium channel blockers; olefin metathesis; Pentacycloundecane; Polycyclic cage; system; Triquinane
Creator
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Young L M; Zeller M; Geldenhuys W J; Malan S F; Van der Schyf C J
Description
An account of the resource
Polycyclic hydrocarbon compounds, also known as "cage compounds", are of interest in drug discovery due to their versatility as scaffolds. Derivatives of both pentacycloundecane-dione and triquinane-dione have been the focus of numerous investigations as multifunctional neuroprotective drugs where these compounds were used as novel drug scaffolds with the ability to cross the blood brain barrier. Here we present the synthesis, characterization and single crystal X-ray analysis for two triquinane synthons; tricyclo[6.3.0.0(2.6)]undecane-4,9-diene-3,11-dione (compound 5 crystallizes in the monoclinic system, unit cell parameters are: a=6.5876 (12) angstrom, b=10.4204 (19) angstrom, c=12.074 (2) angstrom; V=825.4 (3) angstrom(3) and Z=4) and tricyclo[6.3.0.0(2.6)]undecane-3,11-dione (compound 6 crystallizes in monoclinic system, unit cell parameters are: a=7.5992 (7) angstrom, b=10.7294 (10)angstrom, c=10.8664 (10) angstrom; V=884.04 (14) angstrom(3) and Z=4); as well as a triquinane derivative, N-(3-methoxybenzyl)-3,11-azatricyclo[6.3.0.0(2.6)]undecane (compound 11 crystallizes in triclinic system, unit cell parameters are: a = 7.6714 (7) angstrom, b=9.0100 (9) angstrom, c=11.2539 (11) angstrom; V=745.78 (12) angstrom(3) and Z=2). The size and geometrical conformation of the triquinane scaffolds were compared to tetra and pentacycloundecanes, revealing that tricyclo[6.3.0.0(2.6)]-undecane-3,11-dione experiences strain relief resulting in greater flexibility, a more asymmetric molecular shape and larger surface area. However, with the introduction of the aza-bridge in N-(3-methoxybenzyl)-3,11-azatricyclo[6.3.0.0(2.6)]undecane, much of the flexibility and asymmetry is lost again. We also discuss the rearrangement mechanism for the observed retro cycloaddition and reversion, and utilized density functional theory calculations to discuss the photocyclization mechanism of this unique [2 + 2] Diels-Alder system. (C) 2013 Elsevier B.V. All rights reserved.
Identifier
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<a href="http://doi.org/10.1016/j.molstruc.2013.04.030" target="_blank" rel="noreferrer noopener">10.1016/j.molstruc.2013.04.030</a>
Format
The file format, physical medium, or dimensions of the resource
Journal Article
2013
amines
blocker
Chemistry
Crystal structure
derivatives
Geldenhuys W J
Journal Article
Journal of Molecular Structure
L-type calcium channel blockers
Malan S F
olefin metathesis
Pentacycloundecane
Polycyclic cage
system
Triquinane
Van der Schyf C J
Young L M
Zeller M
-
Text
A resource consisting primarily of words for reading. Examples include books, letters, dissertations, poems, newspapers, articles, archives of mailing lists. Note that facsimiles or images of texts are still of the genre Text.
URL Address
<a href="http://doi.org/10.1039/c0sc00544d" target="_blank" rel="noreferrer noopener">http://doi.org/10.1039/c0sc00544d</a>
Rights
Article information provided for research and reference use only. All rights are retained by the journal listed under publisher and/or the creator(s).
Pages
642-648
Issue
4
Volume
2
Search for Full-text
Locate full-text within NEOMED Library's e-journal collections
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Dublin Core
The Dublin Core metadata element set is common to all Omeka records, including items, files, and collections. For more information see, http://dublincore.org/documents/dces/.
Title
A name given to the resource
N-Aryl-substituted 3-(beta-D-glucopyranosyloxy)-2-methyl-4(1H)-pyridinones as agents for Alzheimer's therapy
Publisher
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Chemical Science
Date
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2011
2011
Subject
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4(1h)-pyridinone; biological evaluation; Blood-brain barrier; Chemistry; copper; Crystal structure; derivatives; disease; iron chelators; physicochemical properties; targeting a-beta; transgenic mice
Creator
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Scott L E; Telpoukhovskaia M; Rodriguez-Rodriguez C; Merkel M; Bowen M L; Page B D G; Green D E; Storr T; Thomas F; Allen D D; Lockman P R; Patrick B O; Adam M J; Orvig C
Description
An account of the resource
Molecules designed to sequester, redistribute and/or remove metal ions are attractive therapeutic agents in neurodegenerative diseases such as Alzheimer's disease. The multifactorial nature of the condition and the generally poor target specificity associated with metal ion-binding therapy has led to the development of multifunctional 3-hydroxy-4-(1H)-pyridinone pro-ligands. The excellent qualities of the basic 3-hydroxy-4-pyridinone framework as a low toxicity metal chelator and an antioxidant, as well as its antibacterial and analgesic properties among other functions, inspired us to functionalize it with a framework derived from thioflavin-T, the well-known traditional dye used as a marker to detect amyloid deposits in tissue sections. Thus 2-methyl-3-hydroxy-1-(4-dimethylaminophenyl)-4(1H)-pyridinone(HL1), 2-methyl-3-hydroxy-1-(4-methylaminophenyl)-4(1H)-pyridinone (HL2), 1-(4-aminophenyl)-3-hydroxy-2-methyl-4(1H)-pyridinone (HL3), 1-(6-benzothiazolyl)-3-hydroxy-2-methyl-4(1H)-pyridinone (HL4), 1-(2-benzothiazolyl)-3-hydroxy-2-methyl-4(1H)-pyridinone (HL5) and 2-methyl-3-hydroxy-1-[4-(4-bromophenyl)-2-thiazolyl]-4(1H)-pyridinone (HL6) were obtained. Glycosylation, as well as incorporation of structures mimicking those of known amyloid imaging agents, may target drug action to the site of interest, the metal-overloaded amyloid plaques in the Alzheimer's brain. The pro-ligands were assessed for their antioxidant activity, cytotoxicity and ability to interfere with metal ion-induced amyloid peptide aggregation to screen promising lead compounds. Finally, in a brain uptake study with a radiolabeled glucoconjugate pyridinone, 3-(beta-Dglucopyranosyloxy)-1-[4-(4-[I-125] iodophenyl)-2-thiazolyl]-2-methyl-4(1H)-pyridinone ([I-125]-GL(7)) was shown to cross the blood-brain barrier using an in situ rat brain perfusion technique.
Identifier
An unambiguous reference to the resource within a given context
<a href="http://doi.org/10.1039/c0sc00544d" target="_blank" rel="noreferrer noopener">10.1039/c0sc00544d</a>
Format
The file format, physical medium, or dimensions of the resource
Journal Article
2011
4(1h)-pyridinone
Adam M J
Allen D D
biological evaluation
Blood-brain barrier
Bowen M L
Chemical science
Chemistry
copper
Crystal structure
derivatives
Disease
Green D E
iron chelators
Journal Article
Lockman P R
Merkel M
Orvig C
Page B D G
Patrick B O
physicochemical properties
Rodriguez-Rodriguez C
Scott L E
Storr T
targeting a-beta
Telpoukhovskaia M
Thomas F
Transgenic mice