Buspirone and some of the newer buspirone-like antidepressants have become the alternative to the benzodiazepines and the treatment of choice for patients with anxiety disorders. These drugs are composed of two pharmacologically important parts, arylpiperazine and imide linked by aliphatic chain. Structural modifications involve changes: in the aryl-piperazine moiety, in the imide part and in the length of aliphatic chain. The development of new biologically active structures is connected with deeper understanding of steric and electronic factors.

Considering the interaction of a ligand with 5-HT1A receptor, it was supposed that the distances between the aromatic substituent, nitrogen atom of piperazine and carbonyl group of imide moiety are important for binding of buspirone-like compounds [1,2]. Therefore, the data on the structure, conformational flexibility and properties of functional groups are of interest. Our interest was focused on the configuration of piperazine nitrogen attached to the aromatic moiety. The combined NMR and theoretical studies enabled an improvement of the model of pharmacophore. The results indicate that biological activity of buspirone-like ligands may dependent on the piramidal or flat configuration of the nitrogen atom.

[1] M.F. Hibert, M.W. Gittos, D.N. Middlemiss, A.K. Mir, J.R. Fozard, J. Med. Chem. 31, 1087 (1988); M.F. Hibert, I. McDermott, D.N. Middlemiss, A.K. Mir, J.R. Fozard, Eur. J. Med. Chem. 24, 31 (1989)

[2] Z. Chilmończyk, A. Szelejewska-Woźniakowska, J. Cybulski, M. Cybulski, A.E. Kozioł, M. Gdaniec, Arch. Pharm. Pharm. Med. Chem., 330,146 (1997)

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