Synthesis of 6,8-diaminopurines via acid-induced cascade cyclization of 5-aminoimidazole precursors and preliminary anticancer evaluation

Abstract

Inspired by the pharmacological interest of 6-substituted purine roscovitine for cancer treatment, 5-aminoimidazole-4-carboxamidine precursors containing a cyanamide unit were prepared by condensation of 5-amino-4-cyanoformimidoylimidazoles with a wide range of primary...

Novel Imidazole‐based Hydrazonoyl Cyanides and Amidrazones Containing N(N,O)‐Heterocycles: Selective Synthesis, Reaction Mechanisms and Preliminary Anticancer Evaluation

“…[37] More recently, reaction of imidazoles 1 with cyanamide in the presence of an excess of acetic acid resulted in cyanoimino derivatives that were converted into highly fluorescent 2-amino-6cyanopurines, [38] or 6,8-diaminopurines with potent anticancer activity. [39] Since piperidine, morpholine and piperazine have also been considered privileged heterocyclic moieties in drug design, [40] we decided to conjugate these important scaffolds with the 5aminoimidazole nucleus. Herein, we report the selective synthesis of 5-aminoimidazole-4-N-carboxamidrazones and 5-aminoimidazole-4-hydrazonoyl cyanides incorporating piperidine, morpholine and piperazine moieties, as they represent key synthetic precursors for the preparation of new nitrogen heterocycles.…”