[10-Acyldithranol dimers; new derivatives of the antipsoriatic dithranol; synthesis, characterization and biochemical properties].
With regard to the synthesis of 10-(omega-carboxyacyl)-derivatives dithranol 1 was reacted with the carboxylic acid dichlorides of succinic acid, glutaric acid, adipic acid and pimelic acid in toluene and collidin as a base. Instead of the expected derivatives the 10-acyldithranol dimers 5-7 were isolated as main products except for the reaction of succinyl chloride where only lactone 2 was formed. Moreover the 6-ring lactone 3 as a side product and traces of the 7-ring lactone 4 could also be isolated and characterized. All compounds revealed to be inhibitors of the enzyme glucose-6-phosphate dehydrogenase, indicating antipsoriatic activity.
Berset
J D
JD
Dermatologische Klinik, Universität Bern.
Krebs
A
A
D000875:Anthralin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D055598:Chemical Phenomena; D002621:Chemistry; D005954:Glucosephosphate Dehydrogenase / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D011565:Psoriasis / Q000188:drug therapy*
D005954:Glucosephosphate Dehydrogenase; D000875:Anthralin
10-Acyldithranol-Dimere; Neue Derivate des Antipsoriatikums Dithranol; Syntheseversuche, Charakterisierung und biochemische Eigenschaften.