Potential neurotropic and antiinflammatory agents: 2-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yl sulfides

Abstract

2-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-thiol (VII) was synthesized from 2,10-dichloro-10,11-dihydrodibenzo[b,f]thiepin (IV) and was alkylated with a series of aminoalkyl chlorides which led to amino sulfides IX, XII, XIII, and XVI-XX. The primary amine IXa was transformed by treatment with ethyl chloroformate to the carbamate Xa which was reduced to the methylamino compound XIa. The carbamate XX was similarly reduced to compound XXI. Alkylation of VII with 2-bromoethanol gave the alcohol XIVa which was transformed to the crude tosylate XVa. Its reactions with the corresponding piperazines gave compounds XXII to XXIV. The alcohol XXII was esterified to the decanoate XXV. Reactions of the sodium salt of VII with ethyl chloroacetate, ethyl 2-chloropropionate and ethyl 4-chlorobutyrate gave the corresponding esters which were saponified to acids XXVIb-XXVIIIb. Their amides XXVId to XXVIIId and XXVIe were prepared either via the acid chlorides or via the esters. Out of the compounds prepared only XIa showed a clear profile of a potential antidepressant. The other compounds showed indications of thymoleptic, antiinflammatory and antimicrobial activities.