The specific aims of this project are the synthesis of the pentagonal dodecahedrane, several monosubstituted dodecahedranes, isomeric ring systems represented by ditrigional dodecahedrane, and larger related spherical molecules exemplified by pentakaidecahedrane and hexakaidecahedrne. Also targeted are fundamental studies to functionalize these molecules in order to make possible a wide variety of interesting derivatives. The chemical significance of the proposed research lies in the development of new synthetic methodology. The health relevance lies in the contributions the new compounds could make to our knowledge of influenza inhibition and allied fields. The capability of the above globular carbocyclic ring systems for hydrophobic binding to receptor sites is expected to convey high biological activity , particularly in the antiviral area. The anticipated high degree of lipid solubility, low extent of ionization, and lack of plasma-protein binding should virutually ensure facile and rapid passage into brain and cerebro-spinal fluids. Their efficacy may be associated with their innate ability to penetrate tissues and fluids. Each of the structural types to be prepared satisfies the qualitative criteria of high symmetry and spherical geometry.
| Lagerwall, D R; Gallucci, J C; Paquette, L A (1991) Structure of diethyl 1,2,3,3b,4a,5,6,7,8,8a,8b,9-dodecahydro-1,5-dioxo-4,8,9-metheno-4H-cycl openta [1,2-a:4,3-a']dipentalene-4,10-dicarboxylate. Acta Crystallogr C 47 ( Pt 9):1868-72 |
| Gallucci, J C; Taylor, R T; Kobayashi, T et al. (1989) X-ray crystallographic analysis of the structural distortions induced by substitution and annulation of the dodecahedrane nucleus. Acta Crystallogr C 45 ( Pt 6):893-8 |
