RESUMO
The spirostanic steroidal side-chain of diosgenin and hecogenin was modified to produce 22-oxocholestane derivatives. This type of side-chain was obtained in good yields through a straightforward four-step pathway. These compounds show potent brassinosteroid-like growth promoting activity evaluated via the rice lamina joint inclination bioassay. This is the first report of steroidal skeletons bearing the 22-oxocholestane side-chain and preserving the basic structure (A-D rings) from their corresponding parent compounds acting as plant growth promoters.
Assuntos
Colestanos , Oryza/crescimento & desenvolvimento , Reguladores de Crescimento de Plantas , Colestanos/síntese química , Colestanos/química , Colestanos/farmacologia , Reguladores de Crescimento de Plantas/síntese química , Reguladores de Crescimento de Plantas/química , Reguladores de Crescimento de Plantas/farmacologiaRESUMO
The title steroid, C34H50O6S, is an inter-mediate on the synthetic route between diosgenin and brassinosteroids, which possess the A ring modified with the 2α,3α-diol functionality. The polycyclic spiro-stan system has the expected conformation, with six-membered rings adopting chair forms and the five-membered rings envelope forms (flap atoms are the methine C atom in the C/D-ring junction and the spiro C atom connecting rings E and F). The 3ß-tosyl-ate group is oriented in such a way that S=O bonds are engaged in inter-molecular hydrogen bonds with O-H and C-H donors. Chains of mol-ecules are formed along [100] via O-Hâ¯O hydrogen bonds, and secondary weak C-Hâ¯O inter-actions connect two neighbouring chains in the [001] direction.