"Síntese de compostos anfifílicos derivados de δ-d-gliconolactona, potenciais agentes surfactantes”

Abstract

Surfactants are amphiphilic molecules widely used in many industries. A constant need for products obtained from natural raw materials instead of petroleum derivatives has led to a lot of studies on developing “natural” surfactants derivative from carbohydrates. These compounds are versatile, biodegradable and introduce a wide range of applications, awake the interest of our laboratory and others research groups. Aiming the development of new tensoactives molecules which can also act as antibacterial agents, we describe in this work the preparation of several N-alkyl diamines and one tetra-amine, having an hydrophobic carbonic chain, and its respective gluconamides. Therefore, in this opportunity we describe the synthesis and characterization of amphiphilic compounds obtained from starting long chain alcohols. These compounds were initially treated with methanesulfonyl chloride in dichlorometane and pyridine, leading to the corresponding alkyl mesylates. The aminated intermediates were prepared by substitution of the mesyl group or of chlorine atom of n-octyl-chloride by diamines: 1,2-ethanediamine, 1,3propanediamine or 1,4-butanediamine. The condensation of these aminated intermediates with the δ-D-gluconolactone furnished the final gluconamides. The structures of the obtained compounds were elucidated by infrared spectroscopy, 1H and 13C NMR. Two of the final compounds showed moderate activity against the Mycobacterium tuberculosis.