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Paper | Regular issue | Vol 41, No. 6, 1995, pp.1219-1233
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7030
6-(N-Imidoalkyl)aminoalkylbenzothiazolin-2-ones as Ligands of the Serotoninergic 5-HT1A Receptors

Ousmane Diouf, Patrick Depreux, Daniel Lesieur, Jacques H. Poupaert,* and Daniel H. Caignard

*Ecole de Pharmacie, Université Catholique de Louvain, Avenue E. Mounier 73, B-1200 Bruxelles, Belgium

Abstract

A synthesis of 6-(N-imidoalkyl)aminoalkylbenzothiazolin-2-ones, during which it was necessary to prepare the corresponding 3-methyl-6-(n-N-methylaminoalkyl)benzothiazolin-2-ones using as key intermediates the suitable trifluoromethylalkyl derivatives, is described. This approach allowed access to monomethylated seconary amines which were then reacted with the bromoalkylimides to give the title compounds. All these compounds possess a common alkylimido linking group which was flanked by a 3-methylaminoalkylbenzothiazolin-2-one moiety. The variation of the number of methylene groups linking the central basic nitrogen to the benzothiazolin-2-one and to the imido group as well as the nature of the imido group were studied to delineate the structure-affinity relationships of this series.