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Synthesis and Appetite Suppressant Activity of 1-aryloxy-2-substituted Aminomethyltetrahydronaphthalenes as Conformationally Rigid Analogues of Fluoxetine

Synthesis and Appetite Suppressant Activity of 1-aryloxy-2-substituted Aminomethyltetrahydronaphthalenes as Conformationally Rigid Analogues of Fluoxetine

Kalpana Bhandari, Shipra Srivastava, Girija Shankar, Chandishwar Nath

Bioorg Med Chem. 2006 Apr 15;14(8):2535-44.

PMID: 16337129

Abstract:

Several 1-aryloxy-2-substituted aminomethyltetrahydronaphthalenes (7-21) as conformationally rigid analogues of fluoxetine were synthesized and evaluated for their anorexigenic and antidepressant activities. For SAR studies the related acyclic analogues (22-27) were also prepared. Out of the 21 synthesized compounds, 10 compounds (9, 10, 11, 15, 16, 18, 21, 22, 23 and 27) exhibited significant anorexigenic activity (at 75 micromol/kg). Interestingly, all the compounds (7-20, 22-26) were devoid of antidepressant effect, except for compounds 21 and 27 in which the antidepressant activity was retained. Compound 16 emerged as the most active compound of the series with better anorexigenic activity (97.92%) compared to fluoxetine (76.25%) and even with a clinically used drug sibutramine, thus providing a new structural lead for appetite suppressants.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
CS31043150	Sibutramine Related Compound A			Price

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