Synthesis of a homotrifunctional conjugation reagent based on maleimide chemistry

被引:12
作者
Farha, OK [1 ]
Julius, RL [1 ]
Hawthorne, MF [1 ]
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
基金
美国国家科学基金会;
关键词
maleimide; cysteine; Diels-Alder; Mitsunobu; thiol; homotrifunctional conjugation reagent; 1,3,5-tris(hydroxymethyl)benzene; 1,3,5-tris-(N-maleimidomethyl)benzene;
D O I
10.1016/j.tetlet.2006.02.032
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel homotrifunctional conjugation reagent, 1, 3,5-tris-(N-maleimidomethyl) benzene has been synthesized in high yield with minimum purification. The reactivity of this compound was examined by using L-cysteine as a nucleophile. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2619 / 2622
页数:4
相关论文
共 41 条
[1]   A practical approach to the fused β-carboline system.: Asymmetric synthesis of indolo[2,3-α]indolizidinones via a diastereoselective intramolecular α-amidoalkylation reaction [J].
Ardeo, A ;
García, E ;
Arrasate, S ;
Lete, E ;
Sotomayor, N .
TETRAHEDRON LETTERS, 2003, 44 (46) :8445-8448
[2]   Site directed maleimide bifunctional chelators for the M(CO)3+ core (M=99mTc, Re) [J].
Banerjee, SR ;
Babich, JW ;
Zubieta, J .
CHEMICAL COMMUNICATIONS, 2005, (13) :1784-1786
[3]  
BERNARAB A, 1994, HETEROCYCLES, V38, P1641
[4]   MATRIX METALLOPROTEINASE INHIBITORS CONTAINING A (CARBOXYALKYL)AMINO ZINC LIGAND - MODIFICATION OF THE P1 AND P2' RESIDUES [J].
BROWN, FK ;
BROWN, PJ ;
BICKETT, DM ;
CHAMBERS, CL ;
DAVIES, HG ;
DEATON, DN ;
DREWRY, D ;
FOLEY, M ;
MCELROY, AB ;
GREGSON, M ;
MCGEEHAN, GM ;
MYERS, PL ;
NORTON, D ;
SALOVICH, JM ;
SCHOENEN, FJ ;
WARD, P .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (05) :674-688
[5]  
CHEN LL, 1991, J BIOL CHEM, V266, P18237
[6]   Synthesis on N-alkylated maleimides [J].
Clevenger, RC ;
Turnbull, KD .
SYNTHETIC COMMUNICATIONS, 2000, 30 (08) :1379-1388
[7]   SYNTHESIS OF SYMMETRICALLY TRISUBSTITUTED BENZENE DERIVATIVES [J].
COCHRANE, WP ;
PAUSON, PL ;
STEVENS, TS .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (06) :630-&
[8]   Separation-friendly Mitsunobu reactions: A microcosm of recent developments in separation strategies [J].
Dandapani, S ;
Curran, DP .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (13) :3130-3138
[9]   Preparation of bis(β-trimethylsilylethanesulfonyl)imide and its use in the synthesis of protected amine derivatives [J].
Dastrup, DM ;
VanBrunt, MP ;
Weinreb, SM .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :4112-4115
[10]   The human ATP-binding cassette (ABC) transporter superfamily [J].
Dean, M ;
Rzhetsky, A ;
Allikmets, R .
GENOME RESEARCH, 2001, 11 (07) :1156-1166