Synthesis of lipophilic paramagnetic contrast agents

被引：44

作者：

Baker, WC ^{[1
]}

Choi, MJ ^{[1
]}

Hill, DC ^{[1
]}

Thompson, JL ^{[1
]}

Petillo, PA ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 08期

关键词：

D O I：

10.1021/jo981920r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The facile, high-yielding synthesis of a series of macrocycles 7a-k in 75-100% yield is reported. The transformation of these compounds to their carboxymethylated analogues 8a-k in 75-90% yield and subsequent gadolinium complexes 9a-k provides a series of homologous neutral paramagnetic contrast agents (PCAs) with tunable lipophilicity. Alkylated cationic intermediates 6a-k are prepared in yields of 72-94% from glyoxal adduct of cyclen (5) and slight excesses of alkyl iodides. The methodology is selective for monoalkylation and amenable to large-scale synthesis.

引用

页码：2683 / 2689

页数：7

共 31 条

[1] NEW SYNTHETIC ROUTES TO MACROCYCLIC TRIAMINES [J].

ALDER, RW ;

MOWLAM, RW ;

VACHON, DJ ;

WEISMAN, GR .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (06) :507-508

[2] HIGHLY REGIOSELECTIVE SYNTHESIS OF 1,7-DIPROTECTED 1,4,7,10-TETRAAZACYCLODODECANE DERIVATIVES [J].

ANELLI, PL ;

MURRU, M ;

UGGERI, F ;

VIRTUANI, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1317-1318

[3] Selectivity of macrocyclic aminocarboxylates for alkaline-earth metal ions and stability of their complexes [J].

Chang, CA .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (11) :2347-2350

[4] SYNTHESIS AND CHARACTERIZATION OF 1,7-DIMETHYL-1,4,7,10-TETRA-AZACYCLODODECANE - CRYSTAL-STRUCTURE OF THE NICKEL(II) BROMIDE MONOHYDRATE COMPLEX OF THIS MACROCYCLE - THERMODYNAMIC STUDIES OF PROTONATION AND METAL-COMPLEX FORMATION [J].

CIAMPOLINI, M ;

MICHELONI, M ;

NARDI, N ;

PAOLETTI, P ;

DAPPORTO, P ;

ZANOBINI, F .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1984, (07) :1357-1362

[5] SYNTHESIS OF C-FUNCTIONALIZED AND N-FUNCTIONALIZED DERIVATIVES OF 1,4,7-TRIAZACYCLONONANE-1,4,7-TRIYLTRIACETIC ACID (NOTA), 1,4,7,10-TETRA-AZACYCLODODECANE-1,4,7,10-TETRAYLTETRA-ACETIC ACID (DOTA), AND DIETHYLENENETRIAMINEPENTA-ACETIC ACID (DTPA) - BIFUNCTIONAL COMPLEXING AGENTS FOR THE DERIVATIZATION OF ANTIBODIES [J].

COX, JPL ;

CRAIG, AS ;

HELPS, IM ;

JANKOWSKI, KJ ;

PARKER, D ;

EATON, MAW ;

MILLICAN, AT ;

MILLAR, K ;

BEELEY, NRA ;

BOYCE, BA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09) :2567-2576

[6] NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF LANTHANIDE COMPLEXES WITH A TETRAACETIC TETRAAZA MACROCYCLE - UNUSUAL CONFORMATION PROPERTIES [J].

DESREUX, JF .

INORGANIC CHEMISTRY, 1980, 19 (05) :1319-1324

[7] SYNTHESIS OF NONIONIC GADOLINIUM CHELATES USEFUL AS CONTRAST AGENTS FOR MAGNETIC-RESONANCE-IMAGING - 1,4,7-TRIS(CARBOXYMETHYL)-10-SUBSTITUTED-1,4,7,10-TETRAAZACYCLODODECANES AND THEIR CORRESPONDING GADOLINIUM CHELATES [J].

DISCHINO, DD ;

DELANEY, EJ ;

EMSWILER, JE ;

GAUGHAN, GT ;

PRASAD, JS ;

SRIVASTAVA, SK ;

TWEEDLE, MF .

INORGANIC CHEMISTRY, 1991, 30 (06) :1265-1269

[8] An efficient metal-templated route to C-functionalised derivatives of [12]aneN(4) [J].

Edlin, CD ;

Faulkner, S ;

Parker, D ;

Wilkinson, MP .

CHEMICAL COMMUNICATIONS, 1996, (10) :1249-1250

[9] STOICHIOMETRIC MONO N-FUNCTIONALIZATION OF TETRAAZAMACROCYCLES VIA PHOSPHORYL-PROTECTED INTERMEDIATES [J].

FILALI, A ;

YAOUANC, JJ ;

HANDEL, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05) :560-561

[10] HEPATOBILIARY AND RENAL EXCRETION IN MICE OF CHARGED AND NEUTRAL GADOLINIUM COMPLEXES OF CYCLIC TETRA-AZA-PHOSPHINIC AND CARBOXYLIC-ACIDS [J].

HARRISON, A ;

WALKER, CA ;

PEREIRA, KA ;

PARKER, D ;

ROYLE, L ;

PULUKKODY, K ;

NORMAN, TJ .

MAGNETIC RESONANCE IMAGING, 1993, 11 (06) :761-770

← 1 2 3 4 →