Prototypical polymer-bound chemotherapeutic or herbicidal systems have been synthesized in which bioactive molecules are linked to poly(organophosphazenes) by peptide-coupling techniques. The synthetic procedures were developed first through the use of cyclotriphosphazene small-molecule model systems and with the initial use of simple nonbioactive carboxylic acids. These reactions were then utilized for the synthesis of high-polymeric analogues containing bioactive side groups. The sodium salts of 4-cyanophenol and phenol were allowed to react with (NPCl2)3 or (NPCl2)n to yield derivatives of type [NP(OPh)x-(OC6H4CN)y]3 or n. The 4-cyano groups were then reduced to 4-(aminomethyl)phenoxy units with the use of BH3·THF. Condensation of the pendent amino groups with acetic, propionic, benzoic, acrylic, and nicotinic acids, N-acetylglycine, N-acetyl-DL-penicillamine, p-(dipropylsulfamoyl)benzoic acid, and 2,4-dichlorophen-oxyacetic acid was accomplished with the use of dicyclohexylcarbodiimide. The physical and chemical properties of the products are discussed.
All Science Journal Classification (ASJC) codes
- Organic Chemistry
- Polymers and Plastics
- Inorganic Chemistry
- Materials Chemistry