RESUMEN

A series of C(18)-guggultetrol stereo isomers and C(18)-phytosphingosine regio/stereo isomers were synthesised in a stereoselective fashion involving metal mediated fragmentation, stereoselective reduction, 1,4 O → O silyl migration, and Grubbs' cross metathesis as key steps. d-Fructose was used as a raw material for the preparation of all the analogues. The isophytosphingosine derivatives were evaluated against their 5-LOX (5-lipoxigenase) inhibitory activity.

Asunto(s)

Araquidonato 5-Lipooxigenasa/metabolismo , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/síntesis química , Alcoholes Grasos/síntesis química , Alcoholes Grasos/farmacología , Fructosa/química , Esfingosina/análogos & derivados , Relación Dosis-Respuesta a Droga , Inhibidores Enzimáticos/farmacología , Alcoholes Grasos/química , Estructura Molecular , Esfingosina/síntesis química , Esfingosina/química , Esfingosina/farmacología , Estereoisomerismo , Relación Estructura-Actividad