2,8-DITHIA-DIBENZO[e,h]AZULENES AND THEIR 8-OXA ANALOGS.SYNTHESIS AND ANTI-INFLAMMATORY ACTIVITY

摘要

Synthesis of 2,8-dithia-dibenzo[e,h]azulenes (III, X = S) and their 8-oxa analogs (III, X = O),~1 two novel classes of fused heterocyclic compounds, is described. Starting 11H-dibenzo[b,f]thiepm-10-one, 11H-dibenzo[b,f]oxepin-10-one and its 2-chloro derivative (1a-c) were oxidized to 1,2-diketones (2a-c) which subsequently reacted with 2,2'-dimethyl thiodiglycolate to form fused thiophene ring by Hinsberg cyclization reaction. Substituents at positions C(1) and C(3) were then further transformed in order to obtain aminoalkoxy derivatives 8-11. Structures of regioisomers 6c and 6d were elucidated using two-dimensional NMR techniques. All compounds with tetracyclic skeleton were tested in vitro for their anti-inflammatory activity.