Collect. Czech. Chem. Commun. 1988, 53, 1307-1316

Potential antidepressants: 4-(Aminoalkoxy)thioxanthones

Irena Červená, Jiří Holubek, Emil Svátek and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Four different approaches were used for preparing a series of the title compounds. Reactions of the sodium salt of 4-hydroxythioxanthone (V) with dimethylaminoalkyl chlorides gave the ethers VI and VII. Partial demethylation of VII via the carbamate IX afforded the secondary amine VIII. Reactions of the 4-bromobutoxy compound XI with amines resulted in II, XII, and XIII. Reaction of V with 1-chloro-2,3-epoxypropane and the following treatment of the resulting XIV with 2-propanamine gave the amino alcohol XV. The xanthone III was obtained via XVIII similarly like II. The products, especially II and III are cyclic analogues of the antidepressant and cerebral activator "bifemelane" (I) but they do not exhibit the pharmacological profile of antidepressants.