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Molecular Diversity

, Volume 19, Issue 4, pp 787–795 | Cite as

Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9(10H)-acridinone-1,2,3-triazoles

  • Maryam Mohammadi-Khanaposhtani
  • Maliheh Safavi
  • Reyhaneh Sabourian
  • Mohammad Mahdavi
  • Mahboobeh Pordeli
  • Mina Saeedi
  • Sussan Kabudanian Ardestani
  • Alireza Foroumadi
  • Abbas Shafiee
  • Tahmineh AkbarzadehEmail author
Full-Length Paper

Abstract

A new series of 9(10H)-acridinone-1,2,3-triazole derivatives were designed, synthesized and evaluated for their cytotoxic activity against human breast cancer cell lines. The acridone skeleton was prepared through the Ullman condensation of 2-bromobenzoic acid and anilines. Subsequently, it was functionalized with propargyl bromide. Then, a click reaction of the latter compound and in situ prepared 1-(azidomethyl)-4-methoxybenzene derivatives led to the formation of the desired triazole products. Finally, all products were investigated for their capability to cause cytotoxicity against MCF-7, T-47D, and MDA-MB-231 cell lines. Among them, 2-methoxy-10-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)acridin-9(10H)-one 8c exhibited the most potency \((\hbox {IC}_{50}\,{=}\,11.0\,{\pm }\, 4.8\, \upmu \hbox {M})\) against MCF-7 cells, being more potent than etoposide \((\hbox {IC}_{50}\,{=}\, 12.4\,{\pm }\, 4.7 \upmu \hbox {M})\). Also, apoptosis induced by compound 8c was confirmed via acridine orange/ethidium bromide and Annexin V-FITC/propidium iodide (PI) double staining.

Keywords

Acridone-1, 2, 3-triazoles Cytotoxic activity Click chemistry Breast cancer 

Notes

Acknowledgments

This work was supported by Grant from the Research Council of Tehran University of Medical Sciences under Grant No. 94-01-33-28706.

Supplementary material

11030_2015_9616_MOESM1_ESM.doc (7.4 mb)
Supplementary material 1 (doc 7586 KB)

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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  • Maryam Mohammadi-Khanaposhtani
    • 1
  • Maliheh Safavi
    • 2
  • Reyhaneh Sabourian
    • 3
  • Mohammad Mahdavi
    • 4
  • Mahboobeh Pordeli
    • 5
  • Mina Saeedi
    • 6
  • Sussan Kabudanian Ardestani
    • 5
  • Alireza Foroumadi
    • 4
  • Abbas Shafiee
    • 4
  • Tahmineh Akbarzadeh
    • 1
    • 3
    Email author
  1. 1.Department of Medicinal Chemistry, Faculty of PharmacyTehran University of Medical SciencesTehranIran
  2. 2.Department of BiotechnologyIranian Research Organization for Science and TechnologyTehranIran
  3. 3.Persian Medicine and Pharmacy Research CenterTehran University of Medical SciencesTehranIran
  4. 4.Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research CenterTehran University of Medical SciencesTehranIran
  5. 5.Institute of Biochemistry and Biophysics, Department of BiochemistryUniversity of TehranTehranIran
  6. 6.Medicinal Plants Research Center, Faculty of PharmacyTehran University of Medical SciencesTehranIran

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