Schiff Base Coupling of Cyclic and High-Polymeric Phosphazenes to Aldehydes and Amines: Chemotherapeutic Models

Harry R. Allcock, Paul E. Austin

Research output: Contribution to journalArticlepeer-review

67 Scopus citations

Abstract

Prototype systems have been investigated for the synthesis of polymer-bound chemotherapeutic agents in which bioactive molecules are linked to poly(organophosphazenes) through Schiff base linkages. The sodium salts of the phenols 4-hydroxybenzaldehyde, 2-hydroxy-9-fluorenone, and 4-nitrophenol were allowed to react with hexachlorocyclotriphosphazene (III) to yield hydrolytically stable species of general formula [NP(OArX)2]3 (IV), where X = CHO, C=O, or NO2. The 4-nitrophenolic group of IV was reduced to the corresponding 4-aminophenolic unit with PtO2 and molecular hydrogen. Species IV formed Schiff base products with 2,4-dinitrophenylhydrazine, sulfadiazine, 3-hydroxytyramine, 2-amino-4-picoline, or citral. High-polymeric analogues of IV were synthesized with both phenoxy and OArX side groups (X = CHO, C=O, or NH2) by techniques similar to those used for the cyclic trimers, and the macromolecules formed Schiff base species with 2,4-dinitrophenylhydrazine, sulfadiazine, phenylhydrazine, hydralazine, or citral. The physical and chemical properties of the Schiff base products are discussed.

Original languageEnglish (US)
Pages (from-to)1616-1622
Number of pages7
JournalMacromolecules
Volume14
Issue number6
DOIs
StatePublished - Jan 1 1981

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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