[Synthesis, characterization, racemation and biochemical studies on 10-acylderivatives of chrysarobin:...

The racemic synthesis of three 10-acylderivatives of chrysarobin (1) is described. Senecioylchrysarobin (3), beta-carbethoxypropionylchrysarobin (4) and sorbylchrysarobin (5) were prepared by reaction of (1) with the corresponding carboxylic acid chlorides and collidine as a base in toluene. The separation of the racemates of (3) and (5) on a chiral stationary phase is demonstrated for the first time. All of the new compounds showed an increased potency of inhibition of the enzyme glucose-6-phosphate dehydrogenase, an indication for possible antipsoriatic activity.