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
    An, HY
    Wang, TM
    Mohan, V
    Griffey, RH
    Cook, PD
    [J]. TETRAHEDRON, 1998, 54 (16) : 3999 - 4012
  • [2] [Anonymous], NUCLEOPHILIC AROMATI
  • [3] Armstrong Robert W., 1997, P153
  • [4] SOME ASPECTS OF ANIONIC SIGMA-COMPLEXES
    ARTAMKINA, GA
    EGOROV, MP
    BELETSKAYA, IP
    [J]. 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
    BUGG, TDH
    DUTKAMALEN, S
    ARTHUR, M
    COURVALIN, P
    WALSH, CT
    [J]. BIOCHEMISTRY, 1991, 30 (08) : 2017 - 2021
  • [7] Rapid and efficient solid phase syntheses of cyclic peptides with endocyclic biaryl ether bonds
    Burgess, K
    Lim, D
    BoisChoussy, M
    Zhu, JP
    [J]. TETRAHEDRON LETTERS, 1997, 38 (19) : 3345 - 3348
  • [8] 1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE
    CARPINO, LA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) : 4397 - 4398
  • [9] Combinatorial synthesis of dihydropyridone libraries and their derivatives
    Creswell, MW
    Bolton, GL
    Hodges, JC
    Meppen, M
    [J]. TETRAHEDRON, 1998, 54 (16) : 3983 - 3998
  • [10] FENG Y, 1998, 215 ACS NAT M ACS 2