Synthesis of proline-modified analogues of the neuroprotective agent glycyl-L-prolyl-glutamic acid (GPE)

被引:38
作者
Harris, PWR [1 ]
Brimble, MA [1 ]
Muir, VJ [1 ]
Lai, MYH [1 ]
Trotter, NS [1 ]
Callis, DJ [1 ]
机构
[1] Univ Auckland, Dept Chem, Neuren Pharmaceut Med Chem Grp, Auckland 1000, New Zealand
关键词
proline; neuroprotective; peptide; peptidomimetic;
D O I
10.1016/j.tet.2005.08.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of ten proline-modified analogues of the neuroprotective tripeptide GPE is described. Five of the analogues incorporate a proline residue with a hydrophobic group at C-2 and two further analogues have this side chain locked into a spirolactam ring system. The pyrrolidine ring was also modified by replacing the gamma-CH2 group with sulfur and/or incorporation of two methyl groups at C-5. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10018 / 10035
页数:18
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