OPTICALLY-ACTIVE FLUORINATED BETA-LACTAM BUILDING-BLOCKS - A NOVEL FLUORINATED RETROAMIDE ISOSTERE

被引：16
|
作者：
ABOUABDELLAH, A [1 ]
WELCH, JT [1 ]
机构：
[1] SUNY ALBANY,DEPT CHEM,ALBANY,NY 12222
来源：
TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 06期
关键词：
D O I：
10.1016/0957-4166(94)80050-2
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A new and versatile synthesis of optically active alpha-fluoro-malonamides derivatives from enantiomerically pure 3-fluoro-2-azetidinones is described. A fluorinated retroamide isostere based on these alpha-fluoro-malonamide was introduced into a small peptidomimetic for use as an HIV-1 protease inhibitor.
引用
收藏
页码：1005 / 1013
页数：9
相关论文
共 50 条
  • [21] Biocatalysis for the preparation of optically active beta-lactam precursors of amino acids
    Csomos, P
    Kanerva, LT
    Bernath, G
    Fulop, F
    TETRAHEDRON-ASYMMETRY, 1996, 7 (06) : 1789 - 1796
  • [22] LANTHANOID TRIFLATE CATALYZED CONJUGATE ADDITION OF AMINES TO ALPHA,BETA-UNSATURATED ESTERS - A FACILE ROUTE TO OPTICALLY-ACTIVE BETA-LACTAM
    MATSUBARA, S
    YOSHIOKA, M
    UTIMOTO, K
    CHEMISTRY LETTERS, 1994, (05) : 827 - 830
  • [23] Functionalized, differently fluorinated building-blocks via Michael addition of enamines to γ-fluoro-α-nitroalkenes
    Molteni, M
    Zanda, M
    LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (06) : 566 - 568
  • [24] New functionalized, differently fluorinated building-blocks via Michael addition to γ-fluoro-α-nitroalkenes
    Molteni, Marco
    Consonni, Roberto
    Giovenzana, Tommaso
    Malpezzi, Luciana
    Zanda, Matteo
    JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (07) : 901 - 908
  • [25] OPTICALLY-ACTIVE FLUORINATED CYCLOBUTANE NUCLEOSIDE ANALOGS WITH POTENT ANTI-HERPES ACTIVITY
    AHMAD, S
    BISACCHI, GS
    FIELD, AK
    JACOBS, GA
    TUOMARI, AV
    MCGEEVERRUBIN, B
    VITE, GD
    ZAHLER, R
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (06) : 1215 - 1218
  • [26] Synthesis of novel fluorinated building blocks via halofluorination and related reactions
    Remete, Attila Mario
    Novak, Tamas T.
    Nonn, Melinda
    Haukka, Matti
    Fulop, Ferenc
    Kiss, Lorand
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 2562 - 2575
  • [27] PREVENTION OF SOME TYPES OF INFLAMMATORY DAMAGE USING AA-231-1, A FLUORINATED BETA-LACTAM
    REBOUDRAVAUX, M
    VERGELY, I
    MAILLARD, J
    FAVREAU, C
    KOBAITER, R
    JOYEAU, R
    WAKSELMAN, M
    DRUGS UNDER EXPERIMENTAL AND CLINICAL RESEARCH, 1992, 18 (05) : 159 - 162
  • [28] New versatile fluorinated chiral building blocks: Synthesis and reactivity of optically pure alpha-(fluoroalkyl)-beta-sulfinylenamines
    Arnone, A
    Bravo, P
    Capelli, S
    Fronza, G
    Meille, SV
    Zanda, M
    Cavicchio, G
    Crucianelli, M
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10): : 3375 - 3387
  • [29] Design and synthesis of novel fluorinated amines: promising building blocks for drug discovery
    Lonergan, Dave
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [30] Synthesis of novel enantiopure fluorinated building blocks from acyclic chiral allylsilanes
    Tredwell, M
    Tenza, K
    Pacheco, MC
    Gouverneur, V
    ORGANIC LETTERS, 2005, 7 (20) : 4495 - 4497
12345