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, J. M. ; Lal, Bansi ; Anand, Nitya (2004) Chemo- and stereoselective synthesis of benzocycloheptene and 1-benzoxepin derivatives as α-sympathomimetic and anorexigenic agents Bioorganic & Medicinal Chemistry Letters, 14 (11). pp. 2867-2870. ISSN 0960-894X

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.bmcl.2004.03.064

Abstract

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 500 mg/kg and ED50 75 and 55 mg/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.

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