Síntese de derivados adamantóides diaminados e amino álcoois, potenciais agentes farmacológicos

Abstract

Adamantoids compounds have been the subject of interest since the turn of the 20th century due to its analogy with the diamond structure. The unique structure of adamantane is reflected in their highly differing physical and chemical properties, which can have many applications, including drug design and drug delivery, and is present in a variety of bioactive compounds showing activity against several infectious agents, and in many physiological disorders. Along with amines and especially polyamines which are substances that widely occur in biological material may be involved in many aspects such as growth, cell division and differentiation been considered a potential target for chemotherapy for several, especially infectious diseases. In this context, this paper aims at the preparation of new diamines and amino alcohols adamantoids derivatives, which are potential pharmacological agents. To obtain the desired compounds, 1-adamantane methanol has the hydroxyl group converted into a better leaving group, and then replaced by different amines and amino alcohols. For the synthesis of the 2- adamantanone derivatives it was employed reductive amination with diamines and amino alcohols followed by the reduction with NaBH3CN. It was prepared in this work 19 compounds, including 12 previously unpublished, which were characterized by infrared spectroscopy and 1H and 13C nuclear magnetic resonance. Preliminary biological evaluations were performed and compound 7 showed the best activity on the realized biological assays.