From β-Amino-γ-sultone to Unusual Bicyclic Pyridine and Pyrazine Heterocyclic Systems: Synthesis and Cytostatic and Antiviral Activities

被引：24
作者：
de Castro, Sonia [1 ]
Familiar, Olga [1 ]
Andrei, Graciela [2 ]
Snoeck, Robert [2 ]
Balzarini, Jan [2 ]
Camarasa, Maria-Jose [1 ]
Velazquez, Sonsoles [1 ]
机构：
[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain
[2] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium
来源：
CHEMMEDCHEM | 2011年 / 6卷 / 04期
关键词：
antitumor agents; antiviral agents; cyclization; nitrogen heterocycles; sultones; C-13-LABELED SKIN SENSITIZERS; IMMUNODEFICIENCY-VIRUS TYPE-1; STEREOSPECIFIC SYNTHESIS; HUMAN-CYTOMEGALOVIRUS; CHEMICAL SELECTIVITY; ASYMMETRIC-SYNTHESIS; INHIBITORS; DERIVATIVES; REACTIVITY; HYDROLYSIS;
D O I：
10.1002/cmdc.201000546
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Herein we describe the first successful application of the beta-amino-gamma-sultone system as an intermediate for the synthesis of hitherto virtually unknown 3H-[1,2]-oxathiole [4,3-b]pyridine and pyrazine 1,1-dioxide bicyclic heterocyclic systems. All novel compounds were evaluated for their antiviral and cytostatic activities. Compounds 3a, 15a, and 21a inhibited HIV-1-induced cytopathicity. Compound 7 showed remarkable cytostatic activity, and can be regarded as a potential antitumor candidate for further exploration.
引用
收藏
页码：686 / 697
页数：12
相关论文
共 40 条
  • [1] DIRECTED METALATION OF PYRIDINESULPHONAMIDES - SYNTHESIS OF PYRIDINE-FUSED ISOTHIAZOLES AND 1,2-OXATHIOLES
    ALO, BI
    FAMILONI, OB
    MARSAIS, F
    QUEGUINER, G
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (01) : 61 - 64
  • [2] A novel synthetic route to 2-alkylpropane-1,3-sultones and its application to the synthesis of 2-alkyl derivatives of tramiprosate
    Bachand, Benoit
    Atfani, Mohamed
    Samim, Bita
    Levesque, Sophie
    Simard, Daniel
    Kong, Xianqi
    [J]. TETRAHEDRON LETTERS, 2007, 48 (49) : 8587 - 8589
  • [3] 2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-3'-SPIRO-5''-(4''-AMINO-1',2''-OXATHIOLE-2'',2''-DIOXIDE)PYRIMIDINE (TSAO) NUCLEOSIDE ANALOGS - HIGHLY SELECTIVE INHIBITORS OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 THAT ARE TARGETED AT THE VIRAL REVERSE-TRANSCRIPTASE
    BALZARINI, J
    PEREZPEREZ, MJ
    SANFELIX, A
    SCHOLS, D
    PERNO, CF
    VANDAMME, AM
    CAMARASA, MJ
    DECLERCQ, E
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (10) : 4392 - 4396
  • [4] β-Halo-α,β-unsaturated γ-sultones
    Braverman, Samuel
    Pechenick-Azizi, Tatiana
    Major, Dan T.
    Sprecher, Milon
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (18) : 6824 - 6831
  • [5] Buglass A. J., 1991, CHEM SULFONIC ACIDS
  • [6] Cai Z. R., 2008, [No title captured], Patent No. [US200858315 (A1), 200858315]
  • [7] NOVEL ALDOL-TYPE CYCLOCONDENSATION OF O-MESYL (METHYLSULFONYL) CYANOHYDRINS - APPLICATION TO THE STEREOSPECIFIC SYNTHESIS OF BRANCHED-CHAIN SUGARS
    CALVOMATEO, A
    CAMARASA, MJ
    DIAZORTIZ, A
    DELASHERAS, FG
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (16) : 1114 - 1115
  • [8] Camarasa MJ, 2004, CURR TOP MED CHEM, V4
  • [9] 3'-SPIRO NUCLEOSIDES, A NEW CLASS OF SPECIFIC HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 INHIBITORS - SYNTHESIS AND ANTIVIRAL ACTIVITY OF [2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-XYLO AND RIBOFURANOSE]-3'-SPIRO-5''-[4''-AMINO-1'',2''-OXATHIOLE 2'',2''-DIOXIDE] (TSAO) PYRIMIDINE NUCLEOSIDES
    CAMARASA, MJ
    PEREZPEREZ, MJ
    SANFELIX, A
    BALZARINI, J
    DECLERCQ, E
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (15) : 2721 - 2727
  • [10] SYNTHESIS AND REACTIONS OF 2-ARYL-3-(DIMETHYLAMINO)ACROLEINS
    COPPOLA, GM
    HARDTMANN, GE
    HUEGI, BS
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (01) : 51 - 56
1234