Potential antitumor agents.: 37.: Synthesis and antitumor activity of guanylhydrazones from imidazo[2,1-b]thiazoles and from the new heterocyclic system thiazolo[2′,3′:2,3]imidazo [4,5-c]quinoline

被引:84
作者
Andreani, A
Granaiola, M
Leoni, A
Locatelli, A
Morigi, R
Rambaldi, M
Lenaz, G
Fato, R
Bergamini, C
Farruggia, G
机构
[1] Univ Bologna, Dipartimento Sci Farmaceut, I-40126 Bologna, Italy
[2] Univ Bologna, Dept Biochim G Moruzzi, I-40126 Bologna, Italy
关键词
D O I
10.1021/jm040888s
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
This paper reports synthesis and antitumor activity of new guanylhydrazones from imidazo[2,1-b]thiazoles and from the new heterocyclic system thiazolo[2 ',3 ':2,3]imidazo[4,5-c]quinoline. The compounds were tested as potential antitumor agents at the National Cancer Institute. The effect of the guanylhydrazone of 2-chloro-6-(2,5-dimethoxy-4-nitrophenyl)imidazo[2,1-b]-thiazole-5-carbaldehyde (41) was investigated, and it was found to be an inhibitor of Complex III of the mitochondrial respiratory chain and is able to induce apoptosis in the cell lines HT29 and HL60.
引用
收藏
页码:3085 / 3089
页数:5
相关论文
共 29 条
  • [1] Potential antitumor agents. Part 29: Synthesis and potential coanthracyclinic activity of imidazo[2,1-b]thiazole guanylhydrazones
    Andreani, A
    Leoni, A
    Locatelli, A
    Morigi, R
    Rambaldi, M
    Recanatini, M
    Garaliene, V
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (09) : 2359 - 2366
  • [2] 2-[(E)-3-(6-chloroimidazo[2,1-b]thiazol-5-yl)prop-2-enyl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone: a new inhibitor of NADH dehydrogenase with antitumor activity
    Andreani, A
    Granaiola, M
    Leoni, A
    Locatelli, A
    Morigi, R
    Rambaldi, M
    Lenaz, G
    Fato, R
    Bergamini, C
    [J]. ARKIVOC, 2004, : 76 - 84
  • [3] Andreani A, 2004, ANTICANCER RES, V24, P203
  • [4] Potential antitumor agents .24. Synthesis and pharmacological behavior of imidazo[2,1-b]thiazole guanylhydrazones bearing at least one chlorine
    Andreani, A
    Rambaldi, M
    Leoni, A
    Locatelli, A
    Bossa, R
    Fraccari, A
    Galatulas, I
    Salvatore, G
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (14) : 2852 - 2855
  • [5] ACTIONS OF BIS(GUANYLHYDRAZONES) ON ISOLATED RAT-LIVER MITOCHONDRIA
    BYCZKOWSKI, JZ
    SALAMON, W
    HARLOS, JP
    PORTER, CW
    [J]. BIOCHEMICAL PHARMACOLOGY, 1981, 30 (20) : 2851 - 2860
  • [6] Communication -: Superoxide in apoptosis -: Mitochondrial generation triggered by cytochrome c loss
    Cai, JY
    Jones, DP
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (19) : 11401 - 11404
  • [7] METAIODOBENZYLGUANIDINE INHIBITS COMPLEX-I AND COMPLEX-III OF THE RESPIRATORY-CHAIN IN THE HUMAN CELL-LINE MOLT-4
    CORNELISSEN, J
    WANDERS, RJA
    VANGENNIP, AH
    VANDENBOGERT, C
    VOUTE, PA
    VANKUILENBURG, ABP
    [J]. BIOCHEMICAL PHARMACOLOGY, 1995, 49 (04) : 471 - 477
  • [8] On the involvement of mitochondrial intermembrane junctional complexes in apoptosis
    Crompton, M
    [J]. CURRENT MEDICINAL CHEMISTRY, 2003, 10 (16) : 1473 - 1484
  • [9] Mitoguazone induces apoptosis via a p53-independent mechanism
    Davidson, K
    Petit, T
    Izbicka, E
    Koester, S
    Von Hoff, DD
    [J]. ANTI-CANCER DRUGS, 1998, 9 (07) : 635 - 640
  • [10] de Totero D, 2003, HAEMATOLOGICA, V88, P148