Synthesis, characterization andin vitroanticancer activity of thiabendazole-derived 1,2,3-triazole derivatives

被引:23
作者
El Bourakadi, Khadija [1 ,2 ]
Mekhzoum, Mohamed El Mehdi [1 ]
Saby, Charles [3 ]
Morjani, Hamid [3 ]
Chakchak, Hind [4 ]
Merghoub, Nawal [5 ]
Qaiss, Abou el kacem [1 ]
Bouhfid, Rachid [1 ]
机构
[1] Moroccan Fdn Adv Sci Innovat & Res MAScIR, Composites & Nanocomposites Ctr, Rabat Design Ctr, Rue Mohamed El Jazouli, Rabat 10100, Morocco
[2] Mohammed V Rabat Univ, Lab Chim Organ & Heterocycl, Fac Sci, Rabat, Morocco
[3] UFR Pharm Reims, BioSpect Unit, 51 Rue Cognacq Jay, F-51096 Reims, France
[4] Ctr Natl Rech Sci & Tech CNRST, Unite Appui Tech Rech Sci UATRS, Rabat 10000, Morocco
[5] Moroccan Fdn Adv Sci Innovat & Res MAScIR, Green Biotechnol Ctr, Rabat Design Ctr, Rue Mohamed Al Jazouli, Rabat 10100, Morocco
关键词
ANTICANCER ACTIVITY; AZIDES; LIGATION;
D O I
10.1039/c9nj05685h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of thiabendazole-derived 1,2,3-triazole compounds were synthesized in good yieldsvia1,3-dipolar cycloaddition through click chemistry approach using different chain alkyl azides with 4-(1-(prop-2-yn-1-yl)benzimidazole-2-yl)thiazole in the presence of copper(i) catalyst. These compounds were characterized on the basis of FT-IR,H-1 NMR,C-13 NMR as well as mass spectrometry. The newly synthesized compounds were screened for theirin vitroantiproliferative activity against a panel of three human cancer cell lines (HT29, MDA-MB-231 and SKBR3). Compound4gexhibited significant activity against all the cell lines tested, with IC(50)values ranging from 1.28 and 7.72 mu g mL(-1), inducing caspases 3 and 7, which further confirms the contribution of apoptotic cell death in MCF-7 and MDA-MB-231 cells. This work further demonstrates the anticancer properties of4g, inducing apoptotic cell death, and the structure activity association is also discussed. This product could be a promising chemotherapeutic agent for cancer treatment.
引用
收藏
页码:12099 / 12106
页数:8
相关论文
共 41 条
  • [1] Coumarin-substituted 1,2,4-triazole-derived silver(I) and gold(I) complexes: synthesis, characterization and anticancer studied
    Achar, Gautam
    Shahini, C. R.
    Patil, Siddappa A.
    Malecki, Jan Grzegorz
    Budagumpi, Srinivasa
    [J]. NEW JOURNAL OF CHEMISTRY, 2019, 43 (03) : 1216 - 1229
  • [2] Anti-breast cancer activity of some novel 1,2-dihydropyridine, thiophene and thiazole derivatives
    Al-Said, Mansour S.
    Bashandy, Mahmoud S.
    Al-Qasoumi, Saleh I.
    Ghorab, Mostafa M.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) : 137 - 141
  • [3] A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction
    Appukkuttan, P
    Dehaen, W
    Fokin, VV
    Van der Eycken, E
    [J]. ORGANIC LETTERS, 2004, 6 (23) : 4223 - 4225
  • [4] Barros T., 2015, CARBOHYD RES, V417, P66
  • [5] Bender I.G.W., 1990, US Pat., Patent No. 4962093
  • [6] Predicting the future burden of cancer
    Bray, F
    Moller, B
    [J]. NATURE REVIEWS CANCER, 2006, 6 (01) : 63 - 74
  • [7] Cecilia M., 2009, EUR J MED CHEM, V44, P373
  • [8] Synthesis, X-ray crystal structures and biomimetic and anticancer activities of novel copper(II)benzoate complexes incorporating 2-(4'-thiazolyl)benzimidazole (thiabendazole), 2-(2-pyridyl)benzimidazole and 1,10-phenanthroline as chelating nitrogen donor ligands
    Devereux, Michael
    Shea, Denis O.
    Kellett, Andrew
    McCann, Malachy
    Walsh, Maureen
    Egan, Denise
    Deegan, Carol
    Kgdziora, Kinga
    Rosair, Georgina
    Muelller-Bunz, Helge
    [J]. JOURNAL OF INORGANIC BIOCHEMISTRY, 2007, 101 (06) : 881 - 892
  • [9] Medicinal attributes of 1,2,3-triazoles: Current developments
    Dheer, Divya
    Singh, Virender
    Shankar, Ravi
    [J]. BIOORGANIC CHEMISTRY, 2017, 71 : 30 - 54
  • [10] Triazole: the keystone in glycosylated molecular architectures constructed by a click reaction
    Dondoni, Alessandro
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (06) : 700 - 708