Current Science

Open Access Open Access  Restricted Access Subscription Access

Microwave-Assisted Synthesis and Characterization of Oxime Derivative of Substituted Chalcone and Its Nickel(II) Complex


Affiliations
1 Department of Chemistry, D.A.V. (P.G.) College, Dehradun - 248 001, India
 

In this study, microwave-assisted green synthesis of a complex of Ni (II)-2′,4′-dihydroxy 4-fluoro chalcone oxime has been carried out. The structure of the complex was characterized by elemental analysis, molar conductance, magnetic moment, IR, 1H-NMR, 13CNMR spectroscopic data and thermal studies. IR data showed that Ni(II) is coordinated to the ligand through the phenolic-O and azomethine-N of the latter. TGA studies confirmed the presence of coordinated water molecules. The 1 : 2 metal to ligands stoichiometry was indicated by mole ratio method, which was further confirmed by Job’s method of continuous variation modified by Turner and Anderson. Stability constant (Ks) of the complex determined by mole ratio method was 8.5245. Standard free energy change (ΔG0) for metal–ligand complex formation was found to be –11.7026 K cal/mol at 27 ± 2°C. On the basis of analytical data, octahedral structure has been proposed for the complex. All compounds were tested for antibacterial activity and showed moderate to good activity against Escherichia coli and Staphylococcus aureus at different concentrations. In this study, we report synthesis of oxime derivative of chalcone and its Ni(II) complex in the hope of developing new compounds which might be used as analytical reagents or intermediates in the synthesis of various classes of bioactive compounds.

Keywords

Antibacterial Activity, Chalcone Oxime, Metal Complex, Mole Ratio.
User
Notifications
Font Size

  • Krishanankutty, K. and John, V. D., Antitumor activity of synthetic curcuminoid analogues (1,7-diaryl-1,6-heptadiene-3,5-diones) and their copper complexes. Synth. React. Inorg. Met.–Org. Chem., 2003, 33(2), 343.

  • Lee, Y. S., Lim, S. S., Shin, K. H., Kim, Y. S., Ohuchi, K. and Jung, S. H., Anti-angiogenic and anti-tumor activities of 2hydroxy-4-methoxychalcone. Biol. Pharm. Bull., 2006, 29(5), 1028–1031.

  • Ye, C. L., Liu, J. W., Wei, D. Z., Lu, Y. H. and Qian, F., In vivo antitumor activity by 2,4-dihydroxy-6-methoxy-3,5-dimethylchalcone in a solid human carcinoma xenograft model. Cancer Chemother. Pharm., 2005, 55(5); 447–452.

  • Ye, C. L., Liu, J. W., Wei, D. Z., Lu, Y. H. and Qian, E., In vitro anti-tumor activity of 2,4-diydroxy-6-methoxy-3,5-dimethylchalcone against six established human cancer cell lines. Pharmacol. Res., 2004, 50(5), 505–510.

  • Chang, H. J. et al., Induction of apoptosis by the licochalcone E in endothelial cells via modulation of NF-B and Bcl-2 family. Biol. Pharm. Bull., 2007, 30(12), 2290–2293.

  • Pandey, M. K., Sandur, S. K., Sung, B., Sethi, G., Kunnumakkara, A. B. and Aggarwal, B. B., Butein, a tetrahydroxychalcone, inhibits nuclear factor (NF)-B and NF-B regulated gene expression through direction inhibition of IB kinase on cysteine 179 residue. J. Biol. Chem., 2007, 282(24), 17340–17350.

  • Agharia, E. R. and Dodwad, S. S., Synthesis and X-ray diffraction studies on some copper(II) complexes of naphthalene analogues of 2′-hydroxychalcones. Asian J. Chem., 1996, 8, 449–454.

  • Agharia, E. R., Dodwad, S. S. and Salvi, S. L., X-ray diffraction studies on some nickel(II) and cobalt(II) complexes of 2′hydroxychalcones. Oriental J. Chem., 1996, 12, 251–256.

  • Singh, K., Barwa, M. S. and Tyagi, P., Synthesis and characterization of cobalt(II), nickel(II), copper(II) and zinc(II) complexes with Schiff base derived from 4-amino-3-mercapto-6-methyl-5oxo-1,2,4-triazine. Eur. J. Med. Chem., 2007, 42, 394–402.

  • Lense, F. T., Glover, C. A. and Markham, E. C., Virginia J. Sci., 1942, 3, 14.

  • Ramakrishnaiah, C. H., Naidu, R. S. and Naidu, R. R., Opticalabsorption and electron-spin-resonance spectral studies of copper(II) chalcone complexes in different solvents. J. Indian Chem. Soc., 1986, 63(6), 573–574.

  • Semwal, A. R. and Dangwal, K. L., Green synthesis and characterization of some substituted dihydroxychalcones. Int. J. Sci. Res, 2015, 4(6), 2972–2974.

  • Nardo, J. V. and Dawson, J. H., Spectroscopic evidence for the coordination of oxygen donor ligands to tetrapheyl porphinatozinc. Inorg. Chem. Acta, 1986, 123(4), 9–13.

  • Job, P., Formation and stability of inorganic complexes in solution. Anal. Chem., 1928, 9, 113–203.

  • Turner, S. E. and Anderson, R. C., Spectrophotometric studies on complex formation with sulfosalicylic acid. III. With copper(II). J. Am. Chem. Soc., 1949, 71, 912–914.

  • Papo, N., Shahar, M., Eisenbach, L. and Shai, Y., A novel lyticpeptide composed of DL-amino acids selectively kills cancer cells. J. Biol. Chem., 2003, 278, 21018–21023.

  • Geary, W. T., The use of conductivity measurements in organic solvents for the characterization of coordination compounds. Coord. Chem. Rev., 1971, 7, 81–122.

  • Geary, W. K., Coordination Chemistry Review, Elsevier Publishing Company Amisterdam, 1970.

  • Sharma, P. K., Sen, A. K. and Dubey, S. N., Synthetic, spectral and thermal studies of cobalt(II), nickel(II), zinc(II) and cadmium( II) complexes with amino acid Schiff bases. Indian J. Chem. Sect. A, 1994, 33A, 1031–1033.

  • More, P. G. and Bhalvankar, R. B., Synthesis and characterization of cobalt(II) and nickel(II) complexes of tridentate Schiff bases. J. Indian Chem. Soc., 2006, 83, 113–115.

  • Joseph, B. L., Herbert, F. S. and Graham, R. C., Introduction to Organic Spectroscopy, Macmillan Publ., New York, USA, 1987.

  • Gordy, W., Spectroscopic evidence for hydrogen bonds: effects of chelation on the carbonyl frequency. J. Chem. Phys., 1940, 8, 516.

  • Zaman, M. K., Aryane, M. S., Sultana, N. and Farooq, A., Synthesis and characterization of glibenclamide complexes of magnesium, chromium, cobalt, nickel, zinc and cadmium salts. Pak. J. Pharm. Sci., 2006, 19(2), 114–118.

  • Butcher, R. J. and West, D. X., Structure of the copper (II) complex of 2-aceylpyridine hexamethyleneiminyl thiosemicarbazone [Cu(Lhexim)Br]. Transition Met. Chem., 1993, 18(5), 449–452.

  • Shankar, K., Roshni, R., Saravankumar, K., Reddy, P. M. and Peng, Y., Synthesis of tetraazamacrocyclic Pd II complexes; antibacterial and catalytic studies. J. Indian Chem. Soc., 2009, 86(2), 153–161.

  • Jose, C. V. and Anto Joy, T., Synthesis and characterization of complexes of manganese (ii) with 2-(furan-2-formylimino) benzimidazole and their psycho pharmacological drug potential studies. Int. J. Chem. Sci., 2008, 6(4), 1913–1919.

  • Rai, B. K. and Kumar, M., Synthesis and characterization of Cu(II), Co(II) and Ni(II) complexes with mixed ligands. J. Indian Council Chem., 2003, 20(1), 22–26.

  • Maurya, R. C., Patel, P. and Rajput, S., Synthesis and characterization of mixed-ligand complexes of Cu(II), Ni(II), Co(II), Zn(II), Sm(II), and U(VI)O-2, with a Schiff base derived from the sulfa drug sulfamerazine and 2,2′-bipyridine. Synth. React. Inorg. Met.–Org. Chem., 2006, 33(5), 801–806.

  • Kamogawa, H., Haramoto, Y., Nakazawa, T., Sugiura, H. and Nanasawa, M., 1,3-Dioxolane bearing perfume and herbicide aldehyde residues. Bull. Chem. Soc. Jpn., 1981, 54(5), 1577–1578.

  • Venugopal, P. and Krishnakuty, K., Synthesis and characterization of cobalt-, nickel, copper- and zinc(II) complexes of morin. J. Indian Chem. Soc., 1997, 74(7), 562–563.


Abstract Views: 275

PDF Views: 95




  • Microwave-Assisted Synthesis and Characterization of Oxime Derivative of Substituted Chalcone and Its Nickel(II) Complex

Abstract Views: 275  |  PDF Views: 95

Authors

Kusum Lata Dangwal
Department of Chemistry, D.A.V. (P.G.) College, Dehradun - 248 001, India
A. R. Semwal
Department of Chemistry, D.A.V. (P.G.) College, Dehradun - 248 001, India

Abstract


In this study, microwave-assisted green synthesis of a complex of Ni (II)-2′,4′-dihydroxy 4-fluoro chalcone oxime has been carried out. The structure of the complex was characterized by elemental analysis, molar conductance, magnetic moment, IR, 1H-NMR, 13CNMR spectroscopic data and thermal studies. IR data showed that Ni(II) is coordinated to the ligand through the phenolic-O and azomethine-N of the latter. TGA studies confirmed the presence of coordinated water molecules. The 1 : 2 metal to ligands stoichiometry was indicated by mole ratio method, which was further confirmed by Job’s method of continuous variation modified by Turner and Anderson. Stability constant (Ks) of the complex determined by mole ratio method was 8.5245. Standard free energy change (ΔG0) for metal–ligand complex formation was found to be –11.7026 K cal/mol at 27 ± 2°C. On the basis of analytical data, octahedral structure has been proposed for the complex. All compounds were tested for antibacterial activity and showed moderate to good activity against Escherichia coli and Staphylococcus aureus at different concentrations. In this study, we report synthesis of oxime derivative of chalcone and its Ni(II) complex in the hope of developing new compounds which might be used as analytical reagents or intermediates in the synthesis of various classes of bioactive compounds.

Keywords


Antibacterial Activity, Chalcone Oxime, Metal Complex, Mole Ratio.

References





DOI: https://doi.org/10.18520/cs%2Fv115%2Fi3%2F476-481