23445-16-1Relevant academic research and scientific papers
Chemo- and stereoselective synthesis of benzocycloheptene and 1-benzoxepin derivatives as α-sympathomimetic and anorexigenic agents
Tandon, Vishnu K.,Singh, Kunwar A.,Awasthi, Anoop K.,Khanna,Lal, Bansi,Anand, Nitya
, p. 2867 - 2870 (2007/10/03)
The synthesis and pharmacological evaluation of cis- and trans-6-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ols 4a-c and 5a-c and cis- and trans-4-amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ols 4d-f and 5d-f were carried out. Chemo- and stereoselective synthesis of 5a-f was achieved by reduction of corresponding α-amino ketones 3a-f with LiAl(t-BuO) 3H. cis-4-Amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ol 4d and trans-4-amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ol 5d exhibited marked anorexigenic activity in mice at a dose of LD50 800 and 500mg/kg and ED50 75 and 55mg/kg, respectively, while the analog cis-2,3-dihydroxy-6-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol 8 showed typical α-sympathomimetic activity.
Stereochemical considerations and the antiinflammatory activity of 6-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ols and related derivatives
Wong,Sasso,Jones,Kaminski
, p. 20 - 27 (2007/10/02)
The antiinflammatory activity of a series of 6-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ols and related derivatives were 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.
