Novel 1, 2, 3-triazole-linked norcantharidin analogues: Synthesis and evaluation of growth inhibition in a panel of selected tumor-cell lines

被引:8
作者
Deng, Liping [1 ,2 ]
Yang, Bo [1 ]
He, Qiaojun [1 ]
Hu, Yongzhou [1 ]
机构
[1] Zhejiang Univ, ZJU ENS Joint Lab Med Chem, Sch Pharmaceut Sci, Hangzhou 310058, Peoples R China
[2] Shaoxing Univ, Dept Pharmacol, Inst Chem & Chem Engn, Shaoxing 312000, Peoples R China
关键词
1; 2; 3-triazole-linked; cantharidin; norcantharidin analogues; cycloaddition; tumor cell lines; growth inhibition;
D O I
10.2174/157018008784083992
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Twenty-one 1, 2, 3-triazole-linked norcantharidin analogues have been synthesized by the efficient [3+2]1, 3-dipolar cycloaddition reaction of norcantharidin derivatives with three organic azides. All analogues have been screened for their antiproliferative activity against a panel of tumor cell lines: KB, SMMC-7721, SGC7901, ECA109, HO8910 and K562. Compound 8e showed potency for the treatment of hepatoma, with GI(50) value (19.0 +/- 0.2 mu M) to SMMC-7721 cell line comparable to that of cantharidin (GI(50) value = 33.2 +/- 0.3 mu M).
引用
收藏
页码:225 / 231
页数:7
相关论文
共 22 条
  • [1] DIPOLAR CYCLO-ADDITION REACTIONS OF ORGANIC AZIDES WITH SOME ACETYLENIC-COMPOUNDS
    ABUORABI, ST
    ATFAH, MA
    JIBRIL, I
    MARII, FM
    ALI, AAS
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (05) : 1461 - 1468
  • [2] 1,2,3-TRIAZOLE-[2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-BETA-D-RIBOFURANOSYL]-3'-SPIRO-5''-(4''-AMINO-1'',2''-OXATHIOL 2'',2''-DIOXIDE) (TSAO) ANALOGS - SYNTHESIS AND ANTI-HIV-1 ACTIVITY
    ALVAREZ, R
    VELAZQUEZ, S
    SANFELIX, A
    AQUARO, S
    DECLERCQ, E
    PERNO, CF
    KARLSSON, A
    BALZARINI, J
    CAMARASA, MJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (24) : 4185 - 4194
  • [3] Human β3-adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides
    Brockunier, LL
    Parmee, ER
    Ok, HO
    Candelore, MR
    Cascieri, MA
    Colwell, LF
    Deng, LP
    Feeney, WP
    Forrest, MJ
    Hom, GJ
    MacIntyre, DE
    Tota, L
    Wyvratt, MJ
    Fisher, MH
    Weber, AE
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (18) : 2111 - 2114
  • [4] BRYANS JS, Patent No. 2004074291
  • [5] CANTHARIDIN - POTENT FEEDING DETERRENT TO INSECTS
    CARREL, JE
    EISNER, T
    [J]. SCIENCE, 1974, 183 (4126) : 755 - 757
  • [6] Effector mechanisms of norcantharidin-induced mitotic arrest and apoptosis in human hepatoma cells
    Chen, YN
    Chen, JC
    Yin, SC
    Wang, GS
    Tsauer, W
    Hsu, SF
    Hsu, SL
    [J]. INTERNATIONAL JOURNAL OF CANCER, 2002, 100 (02) : 158 - 165
  • [7] Synthesis of novel norcantharidin derivatives of substituted aromatic amines with improved 1,3-dipolar cycloaddition
    Deng, Liping
    Hu, Yongzhou
    [J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (1-3) : 157 - 163
  • [8] 1,3-Dipolar cycloaddition reaction: Synthesis and configuration of norcantharidin derivatives of substituted aromatic amine
    Deng, Liping
    Hu, Yongzhou
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (03) : 597 - 601
  • [9] Synthesis of novel pyrazole-linked norcantharidin derivatives of substituted aromatic amines with efficient 1,3-dipolar cycloaddition
    Deng, Liping
    Hu, Yongzhou
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2006, 43 (06) : 1715 - 1719
  • [10] 1,3-dipolar cycloaddition reaction: Synthesis of novel 5,6-dehydronorcantharidin derivatives of substituted aromatic amines with potential antitumor activities
    Deng, LP
    Liu, FM
    Wang, HY
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (01) : 13 - 18