Studies on the anti-psoriatic activity and spectroscopy of 10- benzylthio-anthralin and its deuterated analogs

Antipsoriatic anthrones are among the most commonly used topical agents for the treatment of psoriasis. 10-Arylthio-derivatives of anthralin [dithranol; 1,8-dihydroxy-9(10H)-antracenone] are of interest in the search for new antipsoriatic agents. The synthesis of 10-benzylthio-1,8-dihydroxy- 9(10H)-antracenone and its deuterated analogs is described. The application of this information to the design of novel anthrones has resulted in compounds with diminished oxygen radical generating properties which may permit a separation of antipsoriatic and inflammatory effects. The structures of these compounds were confirmed on the basis of ¹³C NMR and DEPT experiment studies, which also led to the revised assignment of the ¹H NMR spectrum. The compounds were evaluated for their ability to inhibit the growth of the human keratinocyte cell line HaCaT. Biological tests showed that 10-benzylthio-1,8-dihydroxy-9(10H)-antracenone slightly inhibited the HaCaT cells.