Solid support synthesis of 14-membered macrocycles containing the thioether bridge via SNAr methodology

被引:23
作者
Kiselyov, AS [1 ]
Eisenberg, S [1 ]
Luo, Y [1 ]
机构
[1] Amgen Inc, Small Mol Drug Discovery, Thousand Oaks, CA 91320 USA
关键词
D O I
10.1016/S0040-4020(98)00598-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient assembly of 14-membered macrocycles utilizing the SNAr of fluorine in 3-fluoro-4-nitrobenzoic acid with the SH of cysteine on solid support is reported. The flexibility of this synthesis, as well as the excellent;purity (>90%) of the final products, are the distinctive characteristics of the resulting library. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:10635 / 10640
页数:6
相关论文
共 41 条
[1]   Solution phase combinatorial chemistry. Discovery of 13- and 15-membered polyazapyridinocyclophane libraries with antibacterial activity [J].
An, HY ;
Wang, TM ;
Mohan, V ;
Griffey, RH ;
Cook, PD .
TETRAHEDRON, 1998, 54 (16) :3999-4012
[2]  
[Anonymous], NUCLEOPHILIC AROMATI
[3]  
Armstrong Robert W., 1997, P153
[4]   SOME ASPECTS OF ANIONIC SIGMA-COMPLEXES [J].
ARTAMKINA, GA ;
EGOROV, MP ;
BELETSKAYA, IP .
CHEMICAL REVIEWS, 1982, 82 (04) :427-459
[5]  
Balkenhohl F, 1996, ANGEW CHEM INT EDIT, V35, P2289
[6]   IDENTIFICATION OF VANCOMYCIN RESISTANCE PROTEIN VANA AS A D-ALANINE - D-ALANINE LIGASE OF ALTERED SUBSTRATE-SPECIFICITY [J].
BUGG, TDH ;
DUTKAMALEN, S ;
ARTHUR, M ;
COURVALIN, P ;
WALSH, CT .
BIOCHEMISTRY, 1991, 30 (08) :2017-2021
[7]   Rapid and efficient solid phase syntheses of cyclic peptides with endocyclic biaryl ether bonds [J].
Burgess, K ;
Lim, D ;
BoisChoussy, M ;
Zhu, JP .
TETRAHEDRON LETTERS, 1997, 38 (19) :3345-3348
[8]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[9]   Combinatorial synthesis of dihydropyridone libraries and their derivatives [J].
Creswell, MW ;
Bolton, GL ;
Hodges, JC ;
Meppen, M .
TETRAHEDRON, 1998, 54 (16) :3983-3998
[10]  
FENG Y, 1998, 215 ACS NAT M ACS 2