THE METAL COMPLEXES OF NOVEL SCHIFF BASE CONTAINING ISATIN: CHARACTERIZATION, ANTIMICROBIAL, ANTIOXIDANT AND CATALYTIC ACTIVITY STUDY

CHARACTERIZATION, ANTIMICROBIAL, ANTIOXIDANT AND CATALYTIC ACTIVITY STUDY

Authors

  • VAIRALAKSHMI M Research and Development Centre, Bharathiar University, Coimbatore, Tamil Nadu, India.
  • PRINCESS R Department of Biotechnology, Mepco Schlenk Engineering College, Sivakasi, Tamil Nadu, India.
  • JOHNSON RAJA S Department of Chemistry, American College, Madurai, Tamil Nadu, India.

DOI:

https://doi.org/10.22159/ajpcr.2019.v12i18.34189

Keywords:

Antimicrobial activity, Catalytic activity, Mixed ligand-metal complexes, Octahedral geometry, Radical scavenging activity

Abstract

Objectives: The aim of our work was to synthesize novel mixed ligand-metal complexes and evaluation of antimicrobial, antioxidant assay, and analysis of catalytic oxidation of cyclohexane.

Methods: The complexes were characterized by means of various physicochemical techniques such as elemental analysis, molar conductance, magnetic susceptibility, infrared (IR), electronic absorption, 1H NMR (proton magnetic resonance), and mass spectral studies. The antimicrobial screening study was done by disc diffusion method. The catalytic activity of the complexes was observed in the oxidation of cyclohexane using eco-friendly hydrogen peroxide as oxidant.

Results: On comparing the 1H NMR and IR spectral data of free ligand and its complexes, it was found to be azomethine (CH=N) proton which is formed in the free ligand. During complexation, the azomethine proton is coordinated to the metal ion and the phenolic oxygen is coordinated to the metal ion by deprotonation. The analytical data and mass spectra of the ligand and the complexes confirm the stoichiometry of metal complexes as being of the (MLY)Cl type and the metal to ligand ratio is 1:1. The antimicrobial, antioxidant, and catalytic potential were evaluated and the result shows the better activity of the complexes than the ligand.

Conclusion: It was found to be copper(II) and zinc(II) complexes which are effective against all the bacteria when compared to standard drug streptomycin. Copper(II) complex was found to be effective antibacterial agent against Aspergillus niger and Aspergillus flavus in comparison to the standard drug Nystatin. The zinc complex exhibited good catalytic activity.

Downloads

Download data is not yet available.

References

da Silva JF, Garden SJ, Pinto AC. The chemistry of isatins: A review from 1975 to1999. J Braz Chem Soc 2001;12:273-324.

Medvedev AE, Clow A, Sandler M, Glover V. Isatin: A link between natriuretic peptides and monoamines? Biochem Pharmacol 1996;52:385-91.

Pushpa H, Naraboli BS, Biradar SJ. Synthesis, characterization, and biological activity of novel N-phenylpropyl-3-substituted indoline-2-one derivatives. Int J Pharm Pharm Sci 2017;9:165-70.

Farhana A, Sadia AD, Hossain MS, Sarker MS. Synthesis, spectral and thermal characterization of selected metal complexes containing Schiff base ligands with antimicrobial activities. Asian J Chem Sci 2018;4:1-19.

Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin mannich bases. Eur J Med Chem 2000;35:249-55.

Pandeya SN, Sriram D, Nath G, De Clercq E. Synthesis, antimicrobial and antioxidant activities of mannich bases derived from 1h-indole-2,3-dione and 3-amino-2-phenylquinazol-4-One. Arzneimittelforsch Drug Res 2000;50:55-9.

Sridhar SK, Pandeya SN, Stables JP, Ramesh A. Anticonvulsant activity of hydrazones, schiff and mannich bases of isatin derivatives. Eur J Pharm Sci 2002;16:129-32.

Pandeya SN, Sriram D. Synthesis and screening for antibacterial activity of Schiff’s and mannich bases of isatin and its derivatives. Acta Pharm Turc 1998;16:33-8.

Vasanthi R, Sundar PS, Ramana H, Rao KN. Synthesis, characterization and antimicrobial evaluation of some novel 3-hydrazone-1hbenzoindol-2(3h)-ones. Indo Am J Pharm Sci 2017;4:3859-63.

Saranyaa K, Lakshmia SS, Mahadevia P, Logesh G. Ternary transition metal complexes of tridentate (ONO) Schiff base: Synthesis, spectroscopic and biological studies. J Chem Pharm Res 2015;7:851-8.

Javad A, Masoud S, Farhad HM, Reza M. One-pot rapid and efficient synthesis of new spiro derivatives of 11H-indeno[1,2- b]quinoxalin-11-one, 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one and isatin-based 2-pyrazolines. ARKIVOC 2006;11:47-58.

Vijay Kumar H, Naik N. Synthesis and antioxidant properties of some novel 5H-dibenz[b,f]azepine derivatives in different in vitro model systems. Eur J Med Chem 2010;45:2-10.

Kumar HV, Kumar CK, Nagaraja N. Synthesis of novel 3-chloro-1-(5H-dibenz [b,f]azepine-5yl)propan-1-one derivatives with antioxidant activity. Med Chem Res 2011;20:101-8.

Lobo V, Patil A, Phatak A, Chandra N. Free radicals, antioxidants and functional foods: Impact on human health. Pharmacogn Rev 2010;4:118-26.

Amin S, Parle A. Synthesis, characterization and antioxidant activity of 2-aryl benzothiazole derivatives. Int J Curr Pharm Res 2018;10:3-8.

Vipin N, Archana G, Dinesh K. Isolation and characterization of endophytic fungi from Calotropis procera for their antioxidant activity. Asian J Pharm Clin Res 2017;10:254-8.

Lucarini M, Pedrielli P, Pedulli GF, Valgimigli L, Gigmes D, Toroda P. Bond dissociation energies of the N-H bond and rate constants for the reaction with alkyl, alkoxyl and peroxyl radicals of phenothiazines and related compounds. J Am Chem Soc 1999;21:11546-33.

Zhou LP, Xu J, Miao H, Wang F, Li X. Catalytic oxidation of cyclohexane to cyclohexanol and cyclohexanone over Co3O4 nanocrystals with molecular oxygen. Appl Catal A Gen 2005;292:223-8.

Biyala MK, Fahmi N, Singh RV. Antifertility and antimicrobial activities of palladium and platinum complexes of 6-nitro-3-(indolin-2-one) hydrazine carbothiamide and 6-nitro-3-indolin-2-one) hydrazine carboxamide. Indian J Chem 2006;45:1999-2005.

Weissenberger A, Proskauer ES, Riddick JA, Toops EE. Organic Solvents: Physical Properties and Methods of Purification Techniques of Organic Chemistry. 3rd ed. New York: Inter Science; 1955.

Vogel AI. Practical Organic Chemistry.4th ed. London: Longman; 1978.

Angellici RJ. Synthesis and Techniques in Inorganic Chemistry. 1st ed. Philadelphia, PA: WB Saunders Company; 1969.

Pelczar MJ, Chan EC, Krieg NR. Microbiology. 5th ed. New York: McGraw-Hill Inc.; 1998.

Kannan N. Laboratory Manual in Microbiology. 1st ed. Palani: Paramount Publication; 1996.

Blois MS. Antioxidant determinations by the use of a stable free radical. Nature 1958;26:1199-200.

Raman N, Sobha S. Synthesis, characterization, DNA interaction and antimicrobial screening of isatin-based polypyridyl mixed- ligand Cu(II) and Zn(II) complexes. J Serb Chem Soc 2010;75:773-88.

Bellamy LJ. Infrared Spectra of Complex Molecules. 2nd ed. London: Mathuen; 1958.

Neelakantan MA, Marriappan SS, Dharmaraja J, Jeyakumar T, Muthukumaran K. Spectral, XRD, SEM and biological activities of transition metal complexes of polydentate ligands containing thiazole moiety. Spectrochim Acta A Mol Biomol Spectrosc 2008;71:628-35.

Lever AB. Inorganic Electronic Spectroscopy. 2nd ed. Amsterdam: Elsevier; 1984.

Kumar DS, Gandhi SR, Sheriff AK. Synthesis, specterial characterization and antimicrobial activity of bidendate Schiff base (N2) transition metal complexes. J Chem Pharm Res 2015;215:416-23.

Antonio C, Massabni P, Corbi PP, Melnikov P, Zacharias A, Rechenberg R. Four new metal complexes with the amino acid deoxyalliin. J Braz Chem Soc 2005;16:718-22.

Hassaan MA. Co (II) and Fe (III) complexes of Schiff bases derived from isatin with some amino acids. J Islam Acad Sci 1991;4:271-4.

Salehzadeh S, Javarsineh SA, Keypour H. Metal complexes of a new potentially heptadentate(N7) tripodal Schiff base ligand: Synthesis, NMR studies and ab initio calculations. J Mol Struct 2006;785:54-62.

Pal SD, Vidhi G, Kishan K, Kiran J. Synthesis and characterization of divalent metal complexes of the macrocyclic ligand derived from isatin and 1,2-diaminobenzene. J Serb Chem Soc 2011;76:385-93.

Bayoumi A, Alaghaz MA, Aljahdali M. Cu(II), Ni(II), Co(II) and Cr(III) complexes with N2O2 chelating Schiff’s base ligand incorporating azo and sulfonamide moieties: Spectroscopic, electrochemical behavior and thermal decomposition studies. Int J Electrochem Sci 2018;8:9399-413.

Brown NM, Nonhebel DC. NMR spectra of intramolecularly hydrogen-bonded compounds II: Schiff bases of ?-diketones and o-hydroxycarbonyl compounds. Tetrahedron 1968;24:5655-64.

Soares JR, Dinis TC, Cunha AP, Almeida LM. Antioxidant activities of some extracts of Thymus zygis. Free Radic Res 1997;26:469-78.

Puri K, Habbu V, Kulkarni V, Kulkarni H. Characterization, in vitro antioxidant and hepatoprotective activity of fungal endophytic extracts of Andrographis paniculata leaves in

Published

07-08-2019

How to Cite

VAIRALAKSHMI M, PRINCESS R, and JOHNSON RAJA S. “THE METAL COMPLEXES OF NOVEL SCHIFF BASE CONTAINING ISATIN: CHARACTERIZATION, ANTIMICROBIAL, ANTIOXIDANT AND CATALYTIC ACTIVITY STUDY: CHARACTERIZATION, ANTIMICROBIAL, ANTIOXIDANT AND CATALYTIC ACTIVITY STUDY”. Asian Journal of Pharmaceutical and Clinical Research, vol. 12, no. 8, Aug. 2019, pp. 206-10, doi:10.22159/ajpcr.2019.v12i18.34189.

Issue

Section

Original Article(s)