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Synthesis and Cytotoxic Activity of 6-Hydroxy-4- Methyl-5,7-(Bis-Phenylazo) Coumarin with Divalent Transition Metal Ions


  • Faculty of Science and Technology, Universiti Sains Islam Malaysia (USIM), Bandar Baru Nilai, 71800 Nilai, Negeri Sembilan, Malaysia


Background/Objectives: One of the severe disease intimidating human health and continues to be a main health problem worldwide is cancer. Hence, discovering new compounds with powerful anticancer activity is of extreme important. The main objective of this paper is the synthesize 6-hydroxy-4-methyl-5,7-(bis-phenylazo) coumarin and its complexes and evaluate the cytotoxic activity of the ligand and complexes against breast cancer cells. Methods/Statistical Analysis: A novel compounds of 6-hydroxy-4-methyl-5,7-(bis-phenylazo) coumarin have been synthesized by 6-hydroxy-4-methylcoumarin. The complexation of nickel (II), copper (II) and cobalt (II) using this ligand gave salt type complexes with the formula of M(C22H15O3N4) the compounds were characterized by microelemental analysis, infra-red, nuclear magnetic resonance spectroscopic techniques and molar conductivity. Cytotoxic activity for the ligand and the complexes were evaluated against breast cancer cells by using MTT assay and the absorbance at 570 nm was measured by ELISA reader. Findings: The CHN analysis of the compounds are in good agreement with the calculated values and the spectroscopic analysis of the complexes indicated that the ligand coordinated to the metal centres as polydentate ligand in bisazocoumarin and form a distorted octahedral arrangement around nickel (II), copper (II) and cobalt (II) centres. The molar conductivity of the divalent metal ions complexes was small which directly supports the fact that all of the investigated complexes are non ionic. The overall results of cells MCF7 breast cancer revealed of cell proliferation was much more highly inhibited by the ligand and complexes Cu, Co and Ni with cell viability 5.21%, 17.36%, 46.20% and 74.43%, respectively at a concentration of 30 mg/ml compared to untreated control cells and IC50 values of the ligands and complexes of Cu, Co and Ni were 1.87, 1.87, 30 and >30 g/ml, respectively. Improvements: Lastly, some suggestions were presented to use these compounds in vivo should be assessed to obtain worthy anticancer drugs.


Bis-Azocoumarin, Breast Cancer MCF7, Complexes of Nickel, Copper and Cobalt, MTT Assay.

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  • Kostova I. Synthetic and natural coumarins as cytotoxic agents. Current Medicinal Chemistry-Anti-Cancer Agents. 2005; 5(1):29–46.‏
  • Shahinian EGH, Haidue I. Synthesis and characterization of new azo coumarin days. U P B Sci Bull. Series B. 2011; 73(4):153–60.
  • El-Ansary AL, Ebeid EM, Omar MM. Emission characteristics of some 8-(arylazo)-7-hydroxy-4-methyl coumarins. Spectrochimica Acta Part A: Molecular Spectroscopy. 1987; 43(5):709–10.
  • Keating GJ, O’Kennedy R. In the chemistry and occurrence of coumarins. O’Kennedy R., Thornes R. D., editors. West Sussex, England: John Wiley and Sons; 1997. p. 23–64.
  • Abdelhafez OM, Amin KM, Batran RZ, Maher TJ, Nada SA, Sethumadhavan S. Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives. Bioorganic and Medicinal Chemistry. 2010; 18(10):3371–8.‏
  • Cordaro M, Grassi G, Risitano F, Scala A. N-substituted and N-unsubstituted 1,3-oxazolium-5-olatescycloaddition reactions with 3-substituted coumarins. Tetrahedron. 2010; 66(14):2713–7.‏
  • Cakici H, Esenpınar AA, Bulut M. Synthesis and characterization of novel phthalocyanines bearing quaternizable coumarin. Polyhedron. 2008; 27(18):3625–30.‏
  • Abdel-Latif SA, Hassib HB, Issa YM. Studies on some salicylaldehyde Schiff base derivatives and their complexes with Cr (III), Mn (II), Fe (III), Ni (II) and Cu (II). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2007; 67(3):950–7.
  • Emara AA. Novel asymmetric tetradentate Schiff base ligands derived from 6-metwia-formyl4-hydroxy-2-(1H)-quinolone and their metal complexes. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry. 1999; 29(1):87–103.‏
  • Sherif OE, Omar MM, Issa MYJ. Intercorrelation between structural and spectroscopic parameters for five 1,3-diketone arylhydrazones derived from dibenzoylmethane. Thermal Analysis. 1993; 39(11):735.
  • Ismail TM. Synthesis, characterization and biological activities of mononuclear and binuclear Fe (III) complexes with some symmetric and unsymmetric Schiff-Base ligands. Journal of Coordination Chemistry. 2006; 59(3):255–70.‏


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