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US 7,605,241 B2Granted
Synthesis of inhibitors of p90Rsk
AssigneeUniversity of Virginia Patent Foundation
InventorsSidney M. Hecht, David J. Maloney
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Abstract
The synthesis of the naturally occurring kaempferol glycoside SLO1O1-1, as well as analogs thereof, has been accomplished, as has its biochemical evaluation. SLO1O1-1 exhibits selective and potent p90 Rsk inhibitory activity at nanomolar concentrations without inhibiting the function of upstream kinases such as MEK, Raf, or PKC. The synthetic scheme of the invention verified the structural assignment of the natural product and has provided access to material sufficient for detailed biological evaluation.
Claims6
A method for synthesizing a compound having the general structure of formula I:
- wherein R1 and R2 are each independently selected from the group consisting of OH and OAc, and R3 is OAc;
- said method comprising;
- synthesizing from naringenin a flavonol (4)
- wherein the conditions for step c1 comprise TFA:H2O (20:2), CH2Cl2, (93%);
- synthesizing a carbohydrate moiety by synthesizing from L-rhamnose compound 5
- synthesizing rhamnosyl bromide from compound 5, and then condensing 4 and the rhamnosyl bromide.
3 more elements
Dependencies are inferred from the claim text.