The principal objectives of the research program outlined herein are the development of methods for the synthesis of functionalized and reactive dodeca-hedrane derivatives, clarification of the mechanisms by which these species react, and systematic structural variation (where possible) to develop structure-activity relationships. In particular, we wish to capitalize on our observations that while secododecahedryl and homododecahedryl amines are modestly good antiviral agents, aminododecahedrane exhibits high toxicity and, in fact, is powerful at inhibiting leukemia cell lines. The potential of this class of compounds makes analysis of their mode of action and clarification of those structural features responsible for the different activities timely and important. No other laboratory in the world is as equipped to deal with this problem as we are. Speculation abounds on the extent and direction of electronic effects capable of operating within the dodecahedrane sphere. We hope to provide quantitative documentation of these phenomena. Controlled polyfunctionalization of dodecahedrane needs to be developed. The new chemistry to be implemented here should concomitantly make available new amino- substituted spherical compounds for appropriate bioassay. In order to broaden the range of useful chemical reactions, it is imperative that we have convenient access to dodecahedryl anions and free radicals. Knowledge of the energetic costs of preparing these intermediates would be invaluable in their deployment. Similarly, the strain energies of several unsaturated compounds, the consequences of tethering dodecahedryl ring systems, and the expectedly rich chemistry of homododecahedrane. derived compounds are to be intensely explored. The heat of formation of dodeca. hedrane is a value of importance to the scientific community as a whole. Finally, we intend to dedicate effort to the elaboration of larger spherical molecules such as pentakai- and hexakaidecahedrane and to obtaining their monoamino derivatives for antiviral bioassay.
| 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 |
