Amino acid amide derivatives of 2-[3-(aminomethyl)-4H-1,2,4-triazol-4-yl]benzophenones, a novel class of annelated peptidoaminobenzophenones

Article abstract of DOI:10.1021/jm00354a015

A series of the title compounds was prepared via condensation of the 3-(aminomethyl)triazolylbenzophenone with N-protected amino acids, followed by deprotection, amination of the 3-[(chloroacetamido)methyl]triazolylbenzophenone, or reduction of the relevant azide derivative. Some of the title compounds were also derived directly from the quinazolines by acid-induced rearrangement, followed by deprotection. These new amino acid amide derivatives of the triazolylbenzophenones were evaluated for central nervous system (CNS) activity. Members of this class of compounds exhibited a high level of CNS activities. For example, 2',5-dichloro-2-[3-[(glycylamino)methyl]-5-methyl-4H-1,2,4-triazol-4-yl ]benzophenone was as active as triazolam, with an ED₅₀ of 0.58 mg/kg (mice, po), against antifighting activity in the foot shock-induced fighting test. Other triazolylbenzophenone derivatives showed similar pharmacological activities.