Novel family of fused tricyclic [1,4]diazepines: Design, synthesis, crystal structures and molecular docking studies

An efficient one-pot strategy for the synthesis of a new family of imidazo[1,4]diazepines has been developed and its mechanism has been proposed, which follows a seven-membered ring closure reaction. The condensation of 2- and 4-imidazolecarboxaldehyde with pyrazole amines provides six compounds 1-6, which are based on two types of fused tricyclic scaffolds. All presented compounds were fully spectroscopically characterized and their structure was unambiguously determined by single crystal X-ray crystallography. Molecular docking studies reveal a high similarity between binding modes of diazepines 1, 6 and eticlopride in the dopamine D-3 receptor, as well as between enantiomers 2S, 6S and nortriptyline in dopamine transporter DAT. (C) 2017 Elsevier Ltd. All rights reserved.