CHELATING LIGANDS FUNCTIONALIZED FOR FACILE ATTACHMENT TO BIOMOLECULES - A CONVENIENT ROUTE TO 4-ISOTHIOCYANATOBENZYL DERIVATIVES OF DIETHYLENETRIAMINEPENTAACETIC ACID AND ETHYLENEDIAMINETETRAACETIC ACID

被引:40
作者
KEANA, JFW
MANN, JS
机构
[1] Department of Chemistry, University of Oregon, Eugene
关键词
D O I
10.1021/jo00296a057
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compounds were synthesized by alkylation of the monoenolates of DTPA and EDTA permethyl esters 3 and 4 with benzyl bromide. The benzylated esters 5 and 6 were nitrated, hydrogenated, and converted to their isothiocyanate derivatives 13 and 14 in good yields. The Gd(III) complex of 4-(isothiocyanatobenzyl)-DTPA 16, a potential contrast-enhancing agent for magnetic resonance imaging (MRI), was prepared. © 1990, American Chemical Society. All rights reserved.
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页码:2868 / 2871
页数:4
相关论文
共 20 条
[1]   SYNTHESIS OF 1-(PARA-ISOTHIOCYANATOBENZYL) DERIVATIVES OF DTPA AND EDTA - ANTIBODY LABELING AND TUMOR-IMAGING STUDIES [J].
BRECHBIEL, MW ;
GANSOW, OA ;
ATCHER, RW ;
SCHLOM, J ;
ESTEBAN, J ;
SIMPSON, DE ;
COLCHER, D .
INORGANIC CHEMISTRY, 1986, 25 (16) :2772-2781
[2]  
Ciana L. D., 1989, J ORG CHEM, V54, P1731
[3]  
CREGGE RJ, 1973, TETRAHEDRON LETT, V26, P2425
[4]   TRANSVERSE RELAXATION OF SOLVENT PROTONS INDUCED BY MAGNETIZED SPHERES - APPLICATION TO FERRITIN, ERYTHROCYTES, AND MAGNETITE [J].
GILLIS, P ;
KOENIG, SH .
MAGNETIC RESONANCE IN MEDICINE, 1987, 5 (04) :323-345
[5]  
GOLDSTEIN EJ, 1984, PHYSIOL CHEM PHYS, V16, P97
[6]  
GOODWIN DA, 1981, J NUCL MED, V22, P787
[7]  
HNATOVICH DJ, 1903, SCIENCE, V220, P613
[8]   GADOLINIUM-LABELED LIPOSOMES CONTAINING PARAMAGNETIC AMPHIPATHIC AGENTS - TARGETED MRI CONTRAST AGENTS FOR THE LIVER [J].
KABALKA, GW ;
BUONOCORE, E ;
HUBNER, K ;
DAVIS, M ;
HUANG, L .
MAGNETIC RESONANCE IN MEDICINE, 1988, 8 (01) :89-95
[9]   SUBSTITUTION-REACTIONS WHICH PROCEED VIA RADICAL-ANION INTERMEDIATES .32. ELECTRON-TRANSFER SUBSTITUTION-REACTIONS - LEAVING GROUPS [J].
KORNBLUM, N ;
ACKERMANN, P ;
MANTHEY, JW ;
MUSSER, MT ;
PINNICK, HW ;
SINGARAM, S ;
WADE, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1475-1481
[10]   COVALENT ATTACHMENT OF CHELATING GROUPS TO MACROMOLECULES [J].
KREJCAREK, GE ;
TUCKER, KL .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1977, 77 (02) :581-585