Synthesis of a conformationally restricted dipeptide analogue and its evaluation as a β-turn mimic

被引:35
作者
De Borggraeve, WM [1 ]
Rombouts, FJR [1 ]
Van der Eycken, EV [1 ]
Toppet, SM [1 ]
Hoornaert, GJ [1 ]
机构
[1] Katholieke Univ Leuven, Organ Synth Lab, B-3001 Louvain, Belgium
关键词
pyrazinone; Diels-Alder; piperidinone; constrained dipeptide; beta-turn mimic;
D O I
10.1016/S0040-4039(01)01080-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dichloropyrazinone 3 was converted into a conformationally restricted dipeptide analogue 8 by means of a Diels-Alder strategy. The beta -turn characteristics of molecule 8 were examined by molecular modeling and NMR spectroscopy. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5693 / 5695
页数:3
相关论文
共 10 条
  • [1] Belvisi L, 2000, EUR J ORG CHEM, V2000, P2563
  • [2] BUYSENS KJ, 1995, TETRAHEDRON, V51, P12463
  • [3] Use of steric interactions to control peptide turn geometry.: Synthesis of type VI β-turn mimics with 5-tert-Butylproline
    Halab, L
    Lubell, WD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) : 3312 - 3321
  • [5] Peptides constrained to type VI beta-turns .2. Antiparallel beta-ladder formation
    Kim, K
    Germanas, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) : 2853 - 2860
  • [6] PROTEIN BETA-TURN MIMETICS .1. DESIGN, SYNTHESIS, AND EVALUATION IN MODEL CYCLIC-PEPTIDES
    RIPKA, WC
    DELUCCA, GV
    BACH, AC
    POTTORF, RS
    BLANEY, JM
    [J]. TETRAHEDRON, 1993, 49 (17) : 3593 - 3608
  • [7] Stereo- and regiochemistry in the (asymmetric) cycloaddition reaction of 5-chloro-2(1H)-pyrazinones with cyclic and monosubstituted alkenes and with a N-acryloyl substituted chiral auxiliary
    Rombouts, FJR
    Vanraes, DAJ
    Wynendaele, J
    Loosen, PK
    Luyten, I
    Toppet, S
    Compernolle, F
    Hoornaert, GJ
    [J]. TETRAHEDRON, 2001, 57 (15) : 3209 - 3220
  • [8] Divergent pathways in the intramolecular Diels-Alder reaction of 2(1H)-pyrazinones substituted at the 3-position with a phenylalkyne containing side chain.
    Tahri, A
    De Borggraeve, W
    Buysens, K
    Van Meervelt, L
    Compernolle, F
    Hoornaert, GJ
    [J]. TETRAHEDRON, 1999, 55 (51) : 14675 - 14684
  • [9] Synthesis of α-carbolines and β-carbolinones via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones
    Tahri, A
    Buysens, KJ
    Van der Eycken, EV
    Vandenberghe, DM
    Hoornaert, GJ
    [J]. TETRAHEDRON, 1998, 54 (43) : 13211 - 13226
  • [10] A NEW SYNTHESIS OF SUBSTITUTED 2(1H)-PYRAZINONES
    VEKEMANS, J
    POLLERSWIEERS, C
    HOORNAERT, G
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (04) : 919 - 923