P. P. Purygin, A. A. Danilin, N. A. Klenova
Mar 1, 1999
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Journal
Pharmaceutical Chemistry Journal
Abstract
Amines and amides of the adamantane series exhibit a broad spectrum of pharmacological activity, including analgesic [1], antiinflammatory [2], anticonvulsive [3], and antivirat [4, 5]. Adamantane and its derivatives are capable of changing the hexagonal packing of methylene groups in the alkyl chains of phospholipids, thus affecting the functional properties of membrane proteins. Data obtained on models of erythrocytic membranes and liposomes showed that remantadine may incorporate into the lipid membranes, modifying their structure and imparting to them a more "liquid-phase" character [6]. In the context of an investigation of the membrane activity of adamantane derivatives and the role of this factor in the antiviral and cytotoxic properties of these compounds, of special interest are amides containing, on the one hand, the adamantyl radical and, on the other hand, an amino acid residue. The purpose of this work was to synthesize some new adamantane-containing amino acids (IIIa, IIIb, and IV) and to study their effects upon the state of hemoglobin and membranes in human blood erythrocytes. The adamantane-containing amino acids IIIa, IIIb, and IV were synthesized by interaction of l-adamantanecarboxylic (I) and (1-adamantyl)acetic (11) acids with glycine, D,L-alanine, and L-valine.