title: [Covalent binding of 1-aminoadamantan derivatives to protein antigens using the isothiocyanate and the imidic acid ester procedures. Part 27: Immunosuppressive agent-antigen conjugates (author's transl)].
abstract: Because of the described immunosuppressive potency of 1-aminoadamantan, the authors prepared conjugates of N-substituted 1-aminoadamantan derivatives with human serum albumin (HSA) and bovine gamma globulin (BGG). To achieve covalent binding of 1-aminoadamantan (1) to HSA and BGG (following the isothiocyanate procedure), 1 was converted to the N-(p-isothiocyanatobenzoyl) derivative of 1-aminoadamantan (4) via the nitro compound (2) and the amino compound (3). The reaction of 4 with HSA and BGG yielded conjugates with thiourea structure. The imidic acid ester hydrochloride (7) and the thioimidic acid ester hydrochloride (11) were prepared from the N-(p-cyanobenzoyl) derivative of 1-aminoadamantan (6) and reacted with HSA and BGG to give conjugates with amidine structure.
mesh_terms: D000547:Amantadine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000941:Antigens; D002626:Chemistry, Pharmaceutical; D007096:Imidoesters; D007166:Immunosuppressive Agents; D011485:Protein Binding; D012709:Serum Albumin; D013861:Thiocyanates; D005719:gamma-Globulins
chemical_list: D000941:Antigens; D007096:Imidoesters; D007166:Immunosuppressive Agents; D012709:Serum Albumin; D013861:Thiocyanates; D005719:gamma-Globulins; D000547:Amantadine
vernacular_title: Kovalente bindung von 1-Aminoadamantanderivaten an Proteinantigene nach dem Isothiocyanat- und dem Imidsäureesterverfahren.