The synthesis and free radical polymerization of N-(4-methacryloyloxyphenyl), 2-(4-methoxyphenyl) acetamide (OM), a methacrylic derivative of 4-methoxyphenylacetic acid (a non-steroidal antiinflammatory compound) is described. Also the introduction of a residue of 4-aminophenol (an analgesic and antipyretic metabolite) has been designed, in order to obtain macromolecules supporting two pharmacological residues with complementary action per repeat unit. The stereochemical configuration of POM chains has been analysed by ~H and 13C n.m.r, spectroscopies; polymers prepared by a free radical mechanism at temperatures of 50 and 70°C, are predominantly syndiotactic and follow a Bernoullian distribution of tactic sequences, with an isotacticity parameter tr = 0.27, very close to that of the free radical polymerization of 4-(methacryloyloxy)acetanilide (tr = 0.26 ), but slightly different to that of methyl methacrylate (a = 0.22). The results are interpreted in terms of the influence of the aromatic character of the side substituents on the pseudoasymmetric quaternary carbon of the methacrylic units.
Посилання на статтю:
Polymers with pharmacological activity: 7. Synthesis and stereochemistry of polymeric derivatives of 4-methoxyphenylacetic acid / Julio San Roman and Alberto Gallardo // Polymer. – 1992. – Vol 33. – P. 2840-2847.