Phosphazene High Polymers with Bioactive Substituent Groups: Prospective Anesthetic Aminophosphazenes

Harry R. Allcock; Paul E. Austin; Thomas X. Neenan

doi:10.1021/ma00231a001

Phosphazene High Polymers with Bioactive Substituent Groups: Prospective Anesthetic Aminophosphazenes

Harry R. Allcock, Paul E. Austin, Thomas X. Neenan

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

Anesthetic residues derived from procaine (4), benzocaine (5), chloroprocaine (6), butyl p-aminobenzoate (7), and 2-amino-4-picoline (8) have been linked to trimeric and high-polymeric phosphazene systems through the arylamino function by nucleophilic replacement of halogen in (NPCl₂)₃ or (NPCl₂)_n. Total halogen replacement occurred with the trimers and 99–100% replacement with the high polymers when forcing reaction conditions were employed. Mixed-substituent “copolymers” containing methylamino and procaino or 2-amino-4-picolino residues in a 50:50 ratio were also prepared in order to increase the solubility of the polymers in water. Comparisons are made between the small-molecule cyclotriphosphazene model systems and the high polymers.

Original language	English (US)
Pages (from-to)	689-693
Number of pages	5
Journal	Macromolecules
Volume	15
Issue number	3
DOIs	https://doi.org/10.1021/ma00231a001
State	Published - 1982

All Science Journal Classification (ASJC) codes

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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title = "Phosphazene High Polymers with Bioactive Substituent Groups: Prospective Anesthetic Aminophosphazenes",

abstract = "Anesthetic residues derived from procaine (4), benzocaine (5), chloroprocaine (6), butyl p-aminobenzoate (7), and 2-amino-4-picoline (8) have been linked to trimeric and high-polymeric phosphazene systems through the arylamino function by nucleophilic replacement of halogen in (NPCl2)3 or (NPCl2)n. Total halogen replacement occurred with the trimers and 99–100% replacement with the high polymers when forcing reaction conditions were employed. Mixed-substituent “copolymers” containing methylamino and procaino or 2-amino-4-picolino residues in a 50:50 ratio were also prepared in order to increase the solubility of the polymers in water. Comparisons are made between the small-molecule cyclotriphosphazene model systems and the high polymers.",

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language = "English (US)",

volume = "15",

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journal = "Macromolecules",

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publisher = "American Chemical Society",

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TY - JOUR

T1 - Phosphazene High Polymers with Bioactive Substituent Groups

T2 - Prospective Anesthetic Aminophosphazenes

AU - Allcock, Harry R.

AU - Austin, Paul E.

AU - Neenan, Thomas X.

PY - 1982

Y1 - 1982

N2 - Anesthetic residues derived from procaine (4), benzocaine (5), chloroprocaine (6), butyl p-aminobenzoate (7), and 2-amino-4-picoline (8) have been linked to trimeric and high-polymeric phosphazene systems through the arylamino function by nucleophilic replacement of halogen in (NPCl2)3 or (NPCl2)n. Total halogen replacement occurred with the trimers and 99–100% replacement with the high polymers when forcing reaction conditions were employed. Mixed-substituent “copolymers” containing methylamino and procaino or 2-amino-4-picolino residues in a 50:50 ratio were also prepared in order to increase the solubility of the polymers in water. Comparisons are made between the small-molecule cyclotriphosphazene model systems and the high polymers.

AB - Anesthetic residues derived from procaine (4), benzocaine (5), chloroprocaine (6), butyl p-aminobenzoate (7), and 2-amino-4-picoline (8) have been linked to trimeric and high-polymeric phosphazene systems through the arylamino function by nucleophilic replacement of halogen in (NPCl2)3 or (NPCl2)n. Total halogen replacement occurred with the trimers and 99–100% replacement with the high polymers when forcing reaction conditions were employed. Mixed-substituent “copolymers” containing methylamino and procaino or 2-amino-4-picolino residues in a 50:50 ratio were also prepared in order to increase the solubility of the polymers in water. Comparisons are made between the small-molecule cyclotriphosphazene model systems and the high polymers.

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Phosphazene High Polymers with Bioactive Substituent Groups: Prospective Anesthetic Aminophosphazenes

Abstract

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