"Aminomalononitrile and Diaminomaleonitrile inspired prebiotic chemistry as a novel multicomponent tool for the synthesis of imidazole purine and pyrimidine derivatives

Title : "Aminomalononitrile and Diaminomaleonitrile inspired prebiotic chemistry as a novel multicomponent tool for the synthesis of imidazole purine and pyrimidine derivatives

Abstract:

Amino imidazole carbonitrile derivatives decorated with a-amino acid side-chains have been synthesized by a multicomponent microwave assisted reaction inspired by the prebiotic chemistry of aminomalononitrile as a tool for generating high chemical diversity. These compounds were used as annulation synthons for the preparation of 8,9- disubstituted-6,9-dihydro-1H-purin-6-ones by reaction with formic acid as a simple C-1 donor reagent. The novel heterocycles were characterized by significant activity against influenza A virus, amino imidazole carbonitrile derivatives showing the highest activity. Thus, the chemical complexity generated by prebiotic chemistry furnished a general tool for the identification of novel antiviral agents.

Audience take-away:

Today, the modernization of the MCC by innovative techniques (e.g. microwave-assisted procedures) furnishes an impressive combination of tools to force and speed-up the production of complex heterocyclic derivatives encompassing the so called “Molecular Evolution-Inspired Synthesis”. In this context, aminomalononitrile (AMN) has been identifed as a common intermediate in the prebiotic chemistry of HCN and NH2CHO, besides to diaminomaleonitrile. AMN is involved in the formation of imidazole intermediates, such as amino imidazole carbonitrile and amino imidazole carboxyamide, which are precursors of purine and pyrimidine nucleobases and analogues.The presentation will be focused on an innovative multicomponent prebiotic chemistry approach for the preparation of amino imidazole carbonitrile and purine derivatives decorated with different a-amino acid side-chains. The synthesis involves a one pot microwave-assisted condensation followed by a solvent free annulation and represent the first link between prebiotic chemistry and modern viruses.

Biography:

Bruno Mattia Bizzarri is Post-Doc researcher and a professor of Organic chemistry at the Department of Ecology and Biology, University of Tuscia. In 2013 he was graduated in Medicinal Chemistry at University of Siena and he received the Ph.D. degree in Green Chemistry in 2017. His research work is mainly focused on the synthesis of natural products by the application of new green chemistry approaches and the investigation of prebiotic chemistry processes in a chemo mimetic view. In particular, he is mainly involved in the development of a multicomponent synthesis for the preparation of selected bioactive compounds starting from prebiotic probe.