Design and synthesis of biomimetic polyacrylamides

✍ Scribed by D. Roizard; A. Brembilla; P. Lochon

• Book ID: 103956044
• Publisher: Elsevier Science
• Year: 1989
• Weight: 519 KB
• Volume: 10
• Category: Article
• ISSN: 0923-1137
• DOI: 10.1016/0923-1137(89)90028-6

✦ Synopsis

Water-soluble biomimetic (co)polyacrylamides have been synthesized. Their preparation requires radical (co)polymerizations of new cyclic monomers in dimethylformamide solution, followed by appropriate chemical modifications. The starting acrylamides are obtained with good yields from acryl chloride and aniline derivatives substituted in the 3, 4-positions by NO2 and NH 2 groups. The aromatic moiety is linked to the acryl group by means of a hydrophobic spacer arm .-type]. For n = O, 4-amino-3-nitroaniline is used as the starting reagent," for n v~ O, symmetrical diaminoalkanes must first be monofunctionalized with the help of SNar reaction carried out on 4-nitro-3-aminochlorobenzene. Benzimidazole rings are then synthesized via reduction of the nitro group with Na2S204 and cyclization with glycolic acid. The first esterolytic tests of picolinate activated ester show enhanced hydrolysis rates, which means that the esterolytic activity of the 2-hydroxymethylbenzimidazole residues is totally retained in the macromolecular structures elaborated, and that the use of appropriate esters shouM result in increased hydrolysis rates induced by hydrophobic complexation.