Synthesis and surfactant properties of novel acrylic acid oligomers containing perfluoro-oxa-alkylene units: an approach to anti-human immunodeficiency virus type-1 agents

Abstract

A new polymeric perfluoro-oxa-alkane diacyl peroxide has been prepared by the reaction of the corresponding perfluoro-oxa-alkane diacid fluoride and hydrogen peroxide under alkaline conditions. The decomposition behavior of this peroxide was quite similar to those of the fluoroalkanoyl peroxides [(R FCOO 2) 2; R F = perfiuoroalkyl and perfluoro-oxa-alkyl groups]. This peroxide decomposed homolytically with decarboxylation to afford the -R F- unit and, in addition, was useful for the introduction of the perfluoro-oxa-alkylene (-R F-) unit into acrylic acid homo- and co-oligomers via a radical process. These new acrylic acid oligomers containing the perfluoro-oxa-alkylene unit were shown to be soluble in water, methanol, ethanol, and tetrahydrofuran and were not only able to reduce the surface tension of water effectively but also to confer a good oil repellency. Furthermore, acrylic acid co-oligomers containing this perfluoro-oxa-alkylene unit were found to be potent and selective inhibitors of human immunodeficiency virus type 1 (HIV-1) in vitro.