Stereochemical considerations and the antiinflammatory activity of 6-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ols and related derivatives.
The antiinflammatory activity of a series of 6-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ols and related derivatives was examined using the reverse passive Arthus reaction (RPAR). The antiinflammatory activity of these compounds was markedly influenced by the stereochemistry of the amino alcohol moiety. The threo diastereomer exhibited activity in the RPAR, while the erythro diastereomer was devoid of any significant antiinflammatory activity. The antiinflammatory activity of the amino alcohols was also significantly influenced by the position and nature of the aromatic substituent. Latentiation of the amino alcohol function resulted in analogues exhibiting antiinflammatory activity equivalent to their amino alcohol precursors. Masking the amino alcohol function as a more stable derivative led to analogues exhibiting an antiinflammatory profile unique to their structural class.
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis*; D001567:Benzocycloheptenes / Q000138:chemical synthesis* / Q000627:therapeutic use; D001681:Biological Assay; D007249:Inflammation / Q000503:physiopathology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051381:Rats; D011917:Rats, Inbred Lew; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000893:Anti-Inflammatory Agents; D001567:Benzocycloheptenes