A general strategy for the synthesis of azapeptidomimetic lactams

被引:24
作者
Broadrup, RL [1 ]
Wang, B [1 ]
Malachowski, WP [1 ]
机构
[1] Bryn Mawr Coll, Dept Chem, Rosemont, PA 19010 USA
基金
美国国家科学基金会;
关键词
peptidomimetic; lactams; azapeptide; mitsunobu reaction;
D O I
10.1016/j.tet.2005.08.029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/ homologated serine-azaalanine derivatives. These include sterically-congested beta-lactams, as well as gamma-butyrolactam and delta-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding alpha-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10277 / 10284
页数:8
相关论文
共 62 条
  • [1] Achilles K, 2000, PHARMAZIE, V55, P798
  • [2] Achilles K, 2000, ARCH PHARM, V333, P243, DOI 10.1002/1521-4184(20008)333:8<243::AID-ARDP243>3.0.CO
  • [3] 2-O
  • [4] Peptidomimetics - Antagonists of the fibrinogen receptors: Molecular design, structures, properties and therapeutic applications
    Andronati, SA
    Karaseva, TL
    Krysko, AA
    [J]. CURRENT MEDICINAL CHEMISTRY, 2004, 11 (09) : 1183 - 1211
  • [5] SYNTHESIS OF OPTICALLY PURE ALPHA-AMINO-ACIDS VIA SALTS OF ALPHA-AMINO-BETA-PROPIOLACTONE
    ARNOLD, LD
    MAY, RG
    VEDERAS, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) : 2237 - 2241
  • [6] CONVERSION OF SERINE BETA-LACTONES TO CHIRAL ALPHA-AMINO-ACIDS BY COPPER-CONTAINING ORGANOLITHIUM AND ORGANOMAGNESIUM REAGENTS
    ARNOLD, LD
    DROVER, JCG
    VEDERAS, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) : 4649 - 4659
  • [7] CONVERSION OF SERINE TO STEREOCHEMICALLY PURE BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA BETA-LACTONES
    ARNOLD, LD
    KALANTAR, TH
    VEDERAS, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) : 7105 - 7109
  • [8] Aube J, 1997, ADV AMIN AC MIM PEPT, V1, P193
  • [9] Novel azapeptide inhibitors of hepatitis c virus serine protease
    Bailey, MD
    Halmos, T
    Goudreau, N
    Lescop, E
    Llinàs-Brunet, M
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (15) : 3788 - 3799
  • [10] Efficient synthesis of 1-heterocyclic-3-aminopyrrolidinones
    Bell, IM
    Beshore, DC
    Gallicchio, SN
    Williams, TM
    [J]. TETRAHEDRON LETTERS, 2000, 41 (08) : 1141 - 1145