Synthesis and characterization of new 10-acylderivatives of the antipsoriatic agent dithranol: coupling products of dithranol with all-trans-retinoic acid, 13-cis-retinoid acid and an aromatic analogue of retinoic acid: all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl- nona-2,4,6,8-tetraenoate.
The synthesis of new 10-acylderivatives of dithranol 1 is described. Compound 1 was reacted with the acid chlorides of all-trans retinoic acid 5, 13-cis-retinoic acid 6 and all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-nona-2,4,6,8- tetraenoate 7 in toluene and collidin as a base to give the coupling products 2, 3 and 4. The different structures were confirmed by high resolution 1H- and 13C-NMR spectroscopy. Initial investigations with the enzyme glucose-6-phosphate dehydrogenase indicate that all of them are inhibitors of the protein and therefore might have antipsoriatic activity.
Berset
J D
JD
Dermatologische Klinik Universität Bern.
Krebs
A
A
D017255:Acitretin; D000875:Anthralin / Q000737:chemistry*; D015474:Isotretinoin / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011565:Psoriasis / Q000188:drug therapy*; D014212:Tretinoin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
D014212:Tretinoin; D015474:Isotretinoin; D017255:Acitretin; D000875:Anthralin