Show simple item record

dc.contributor.authorYoung, Lois-May
dc.contributor.authorZeller, Matthias
dc.contributor.authorGeldenhuys, Werner J.
dc.contributor.authorMalan, Sarel F.
dc.contributor.authorVan der Schyf, Cornelis J.
dc.identifier.citationYoung, L.M. (2013). Triquinane scaffolds: Shape and geometry as a function of saturation and bridgehead groups. Journal of Molecular Structure, 1045: 86-94en_US
dc.description.abstractPolycyclic 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]undecane-4,9-diene-3,11-dione (compound 5 crystallizes in the monoclinic system, unit cell parameters are: a = 6.5876 (12) A, b = 10.4204 (19) A, c = 12.074 (2) A; V = 825.4 (3) A3 and Z = 4) and tricyclo[,6]undecane-3,11-dione (compound 6 crystallizes in monoclinic system, unit cell parameters are: a = 7.5992 (7) A, b = 10.7294 (10) A, c = 10.8664 (10) A; V = 884.04 (14) A3 and Z = 4); as well as a triquinane derivative, N-(3-methoxybenzyl)-3,11-azatricyclo[,6]undecane (compound 11 crystallizes in triclinic system, unit cell parameters are: a = 7.6714 (7) A, b = 9.0100 (9) A, c = 11.2539 (11) A; V = 745.78 (12) A3 and Z = 2). The size and geometrical conformation of the triquinane scaffolds were compared to tetra and pentacycloundecanes, revealing that tricyclo[,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]undecane, much of the flexibility and asymmetry is lost again. We also discuss the rearrangement mechanism for the observed retro cycloaddition and reversion, 0022-2860/$en_US
dc.subjectPolycyclic cageen_US
dc.subjectCrystal structureen_US
dc.subjectL-type calcium channel blockersen_US
dc.titleTriquinane scaffolds: Shape and geometry as a function of saturation and bridgehead groupsen_US

Files in this item


There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record