A traceless solid-supported synthesis of novel pyrazinediazepinedione derivatives

被引:9
作者
Mieczkowski, Adam [1 ]
Jurczak, Janusz [1 ,2 ]
机构
[1] Warsaw Univ, Dept Chem, PL-02093 Warsaw, Poland
[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
关键词
VASOPRESSIN RECEPTOR ANTAGONISTS; BETA-TURN MIMETICS; DESIGN;
D O I
10.1016/j.tet.2010.01.064
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, convenient, six-step synthesis of novel, tricyclic pyrazinebenzodiazepinedione derivatives has been described. The strategy is based on the use of the orthogonally-protected, optically pure, (S)-piperazine-2-carboxylic acid, in a Petasis reaction, followed by coupling with anthranilic acid and finally cyclizing cleavage. The investigated method was applied for the synthesis of novel bicyclic pyrazinediaze-pinedione derivatives. This traceless, solid-supported approach allows the preparation of a wide variety of compounds in moderate yields from commercially available or easily obtainable reagents. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2514 / 2519
页数:6
相关论文
共 23 条
  • [1] 1,2,3-triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a][1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding
    Bertelli, L
    Biagi, G
    Giorgi, I
    Livi, O
    Manera, C
    Scartoni, V
    Martini, C
    Giannaccini, G
    Trincavelli, L
    Barili, PL
    [J]. FARMACO, 1998, 53 (04): : 305 - 311
  • [2] Solid-phase synthesis of 1,4-benzodiazepine-2,5-diones. Library preparation and demonstration of synthesis generality
    Boojamra, CG
    Burow, KM
    Thompson, LA
    Ellman, JA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) : 1240 - 1256
  • [3] A new entry to [1,2,4]triazolo[1,5-a][1,4]benzodiazepin-6-ones via intramolecular nitrilimine cycloaddition to the cyano group
    Broggini, G
    Garanti, L
    Molteni, G
    Zecchi, G
    [J]. TETRAHEDRON, 1998, 54 (49) : 14859 - 14868
  • [4] Bunin B. A., 1998, The Combinatorial Index, P77
  • [5] Di Braccio Mario, 2005, Farmaco (Lausanne), V60, P113, DOI 10.1016/j.farmac.2004.12.005
  • [6] Bridged bicyclic vasopressin receptor antagonists V2-selective or dual V1a/V2 activity
    Dyatkin, AB
    Hoekstra, WJ
    Hlasta, DJ
    Andrade-Gordon, P
    de Garavilla, L
    Demarest, KT
    Gunnet, JW
    Hagemann, W
    Look, R
    Maryanoff, BE
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (21) : 3081 - 3084
  • [7] Pyridobenzodiazepines:: A novel class of orally active, vasopressin V2 receptor selective agonists
    Failli, AA
    Shumsky, JS
    Steffan, RJ
    Caggiano, TJ
    Williams, DK
    Trybulski, EJ
    Ning, XP
    Lock, Y
    Tanikella, T
    Hartmann, D
    Chan, PS
    Park, CH
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (04) : 954 - 959
  • [8] FRUSCELLA P, 2002, BIOORG MED CHEM LETT, V12, P1881
  • [9] Design and development of 2,3-benzodiazepine (CFM) noncompetitive AMPA receptor antagonists
    Gitto, R
    Zappalà, M
    De Sarro, G
    Chimirri, A
    [J]. FARMACO, 2002, 57 (02): : 129 - 134
  • [10] 1,5-benzodiazepines Part XIII.: Substituted 4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-amines and 4H-imidazo[1,2-a][1,5]benzodiazepin-5-amines as analgesic, anti-inflammatory and/or antipyretic agents with low acute toxicity
    Grossi, G
    Di Braccio, M
    Roma, G
    Ballabeni, V
    Tognolini, M
    Calcina, F
    Barocelli, E
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (12) : 933 - 944