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four lowest energy solution conformations of (+)-spongistatin 1 (1.27) were determined. The
results suggest that the western hemisphere including the ABEF rings have a common
conformation that does not change between the four lowest energy states (Figure 1.9). The
eastern hemisphere including the DC rings have structurally significant differences in
conformations between the four lowest energy states. This data suggested that the western
hemisphere is rigid, while the eastern hemisphere is more flexible. It was hypothesized that
the binding domain was located within the conformationally rigid portion of the molecule.
Subsequently, analogues of (+)-spongistatin 1 (1.27) were constructed, which maintained the
western hemisphere and ABEF rings, but had a simplified eastern hemisphere (Figure 1.9).
Figure 1.9 A pharmacophore analogue (1.28) of (+)-spongistatin 1 (1.27).
Compound 1.28 represents a thirty-step decrease in its construction when compared
to the natural product (1.27), and maintained nM activity with an IC50 of 60.5 nM in a U937
lymphoma cell line (1.27 displayed an IC50 of 0.06 nM). SAR compliments total synthesis
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