Dual side-reactions limit the utility of a key polymer therapeutic precursor

被引:29
作者
Devenish, SRA
Hill, JB
Blunt, JW
Morris, JC
Munro, MHG
机构
[1] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand
[2] Univ Adelaide, Sch Chem & Phys, Adelaide, SA 5005, Australia
关键词
pMAOS; pHPMA; NHS ester; NMR spectroscopy; structure elucidation; chemoselectivity;
D O I
10.1016/j.tetlet.2006.02.131
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In contrast to literature reports, the activated polyacid poly(methacryloxysuccinimide) reacts with nucleophiles to give, initially, a high proportion of ring-opened residues. This copolymer then reacts intramolecularly to form a polymer with a high fraction of glutarimide residues. These side reactions occur to such an extent as to preclude the use of poly(methacryloxysuccinimide) as a precursor to polymethacrylamides. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2875 / 2878
页数:4
相关论文
共 16 条
[1]   Drug delivery systems: Entering the mainstream [J].
Allen, TM ;
Cullis, PR .
SCIENCE, 2004, 303 (5665) :1818-1822
[2]  
Bilim V, 2003, CURR OPIN MOL THER, V5, P326
[3]   SYNTHESIS OF NITROXIDES FOR USE AS PROCATIONIC LABELS AND THEIR INCORPORATION INTO NAFION FILMS [J].
DEGRAND, C ;
LIMOGES, B ;
BLANKESPOOR, RL .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2573-2577
[4]   The dawning era of polymer therapeutics [J].
Duncan, R .
NATURE REVIEWS DRUG DISCOVERY, 2003, 2 (05) :347-360
[5]  
Godwin A, 2001, ANGEW CHEM INT EDIT, V40, P594, DOI 10.1002/1521-3773(20010202)40:3<594::AID-ANIE594>3.0.CO
[6]  
2-P
[7]  
Godwin A., 2001, ANGEW CHEM, V113, P614
[8]   Synthesis of precursors of poly(acryl amides) by copper mediated living radical polymerization in DMSO [J].
Monge, S ;
Haddleton, DM .
EUROPEAN POLYMER JOURNAL, 2004, 40 (01) :37-45
[9]   FORMATION OF UNUSUAL SIDE-PRODUCTS FROM SUCCINIMIDYL ESTERS OF FATTY-ACIDS DURING THE ACYLATION OF AMINO-ACIDS [J].
PAQUET, A ;
BERGERON, M .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (14) :1806-1808
[10]   An information rich biomedical polymer library [J].
Pedone, E ;
Li, XW ;
Koseva, N ;
Alpar, O ;
Brocchini, S .
JOURNAL OF MATERIALS CHEMISTRY, 2003, 13 (11) :2825-2837