[Synthesis, characterization, racemation and biochemical studies on 10-acylderivatives of chrysarobin: sorbylchrysarobin, beta-carbethoxypropionylchrysarobin and senecioylchrysarobin].
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.
Berset
J D
JD
Dermatologische Klinik der Universität Bern.
Krebs
A
A
D000873:Anthracenes / Q000138:chemical synthesis* / Q000494:pharmacology; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D005954:Glucosephosphate Dehydrogenase / Q000037:antagonists & inhibitors
D000873:Anthracenes; D000894:Anti-Inflammatory Agents, Non-Steroidal; C063892:10-senecioylchrysarobin; C063893:10-beta-carbethoxypropionylchrysarobin; C063894:10-sorbylchrysarobin; C013883:chrysarobin; D005954:Glucosephosphate Dehydrogenase
Syntheseversuche, Charakterisierung, Razemattrennung und biochemische Eigenschaften von 10-Acylderivaten des Chrysarobins: Sorbylchrysarobin, beta-Carbethoxypropionylchrysarobin und Senecioylchrysarobin.