SYNTHESIS, CHARACTERIZATION, ANTI-MICROBIAL, ANTI-CANCER, AND ANTI-OXIDANT ACTIVITY OF NOVEL 1-(NAPHTHALEIN 2-YL OXY)(PHENYL)(METHYL) THIOUREA MANNICH BASE AND ITS METAL COMPLEXES

Authors

  • M. Sivakami Department of Chemistry, SRM UNIVERSITY, KATTANKULATHUR,CHENNAI
  • B. Natarajan Department of Chemistry, SRM University, Kattankulathur, Tamilnadu, India
  • M. Vijayachandrasekar Department of Chemistry, SRM University, Kattankulathur, Tamilnadu, India
  • S. Ram Kumar Pandian Department of Biotechnology, Kalasalingam University, Tamilnadu, India.
  • Krishnan Sundar Department of Biotechnology, Kalasalingam University, Tamilnadu, India

Keywords:

Mannich base, Spectral studies, Antimicrobial activity and Anti-cancer activity

Abstract

ABSTRACT

Objective: Mannich bases of 2-naphthol are predominantly popular in metal-mediated and ligand-accelerated catalysis of enantioselective carbon-carbon bond formation. Since these compounds have multiple centre for chelation with metal ions, they are likely to be potent inhibitors of metallo-enzymes. A number of pharmaceutical and agricultural agents have a naphthalein frame work. Our present study focuses on the synthesis of Mannich base derived from the condensation of 2-naphthol, benzaldehyde and thiourea and its metal complexes and their biological activities.

Methods: The ligand 1-(naphthalein -2-yloxy )(phenyl)(methyl) thiourea (BNBTU) was synthesized by Mannich condensation reaction  between 2- naphthol, benzaldehyde and thiourea in 1:1:1 molar ratio. Mn(II), Co(II), Ni(II), Cu(II)  and Zn(II) complexes of the new Mannich base BNBTU have been synthesized.

Results: The anti-bacterial activity of the ligand and all the metal complexes leads to the conclusion that most of the complexes were found to have activities against E.coli    and B. subtilis. The cytotoxic effects of the newly synthesized ligand have been found good inhibition activity against the cancer cell line. Further the ligand and the metal complexes have been screened for their fungicidal and anti-oxidant properties and they are found to be significantly active.

Conclusion: The ligand 1-(naphthalein -2-yloxy )(phenyl)(methyl) thiourea (BNBTU) has shown as one of the novel ligand and its coordination with transition metals exhibited enhanced biological activity.

Downloads

Download data is not yet available.

Author Biography

M. Sivakami, Department of Chemistry, SRM UNIVERSITY, KATTANKULATHUR,CHENNAI

Assistant Professor,

Department of Chemistry,

Faculity of Engg & Technology,

SRM University. Chennai. 

References

References:

Al-Jeboori, M.J., A.J. Abdul Ghani, A.J. Al-Karawi (2008) Synthesis and structural

studies of new Mannich base ligands and their metal complexes. Transition Met Chem.,

, 925-930.

Deshmukh, M.D. and A.G. Doshi (1995) Synthesis of new Schiff bases and their

antimicrobial activity. Orient J Chem, 11, 85-86.

Haidue, I. and C. Silvestru (1990) Metal compounds in cancer chemotherapy. Coord

Chem Rev., 99, 253-296.

E. Malhotra, N. K. Kaushik, and H. S. Malhotra, Synthesis and studies of ionic chelates of hafnocene with guanine,†Indian Journal of Chemistry, vol. 45, no. 2, pp. 370–376, 2006.

Holla, B.S., M.K. Shivananda, M.S. Shenoy and G.Antony (1998) Synthesis and

characterization of some Mannich bases carrying halophenylfuryl moieties as promising

antibacterial agents. Farmaco,53, 531-535.

Holla, B.S., B .Veerendra, M.K. Shivananda and B .Poojary (2003) Synthesis

characterization and anticancer activity studies on some Mannich bases derived from

,2,4-triazoles. Eur. J. Med.Chem.,38, 759-767.

Gokce, E., G. Bakir, M.F. Sahin, E. Kupeli and E. Yesilada (2005) Synthesis of new

Mannich bases of arylpyridazinones as analgesic and anti-inflammatory agents. Arzneim.

Forsch.,55, 318-325.

Dimmock, J.R., S.S. Jonnalagadda, O.A. Phillips, E. Erciyas, K. Shyam and H.A.

Semple(1992) Anticonvulsant properties of some Mannich bases of conjugated arylidene

ketones. J. Pharm. Sci., 81, 436-440.

Lopes,F., R.Capela, J.O.Goncaves, P.N.Horton, M.B.Hursthouse, J.Iley,

C.M. Casimiro, J. Bom and R. Moreire (2004) Amidomethylation of amodiaquine:

antimalarial N-Mannich base derivatives. Tetrahedron Lett., 45, 7663-7666.

Sriram, D., T.R. Bal and P .Yogeesswari (2005) Synthesis, antiviral and antibacterial

activities of Isatin Mannich bases. Med. Chem. Res., 14, 11-28.

Horodysky,A.G.;Kaminski,J.M.US Patent,US 4394 278, 1983.

Knabe, J., H.P. Buch and W .Schmitt (1983) Derivatives of barbituric acid cytostatic

and CNS activities of chiral barbiturate Mannich-bases. Arch. Pharm. Chem. Life Sci.,

, 1051-1053.

Paul,N.K.;Dietrich,L.M.;Jha,a.Synth.Commun.2007,37,877.

Jha,A.;Paul,N.K.;Trikha,S.;Cameron,T.S.Can.J.Chem.2006,84,843.

N.Raman,S.Esther and C.Thangaraja,J.Chem.Sci.,2004,116,209.

A.B.P Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, 1968.

R.S. Drago, Physical Methods in Inorganic Chemistry, Affiliated East West press, New Delhi, 1978.

C.K. Jorgensen, Advan. Chem. Phys., 1963, 5, 33.

AliakbarDehnoKhalaji, Der chemicaSinica.,2011, 2(6), 7.

Seema I Habib, Mohammed A Baseer and Prafullakumar A Kulkarni, Der chemicaSinica, 2011, 2(1), 27.

Penner-Hahn J E, Indian J Chem A, 2002, 41, 13-21.

Chandra, S.; Gupta, L. K. J. Indian Chem. Soc. 2004, 81, 833–836.

Lever, A. B. P. Inorganic Electronic Spectroscopy, Elsevier, New York, 1968.

Nakamato K., Infrared and Raman Spectra of Inorganic and Coordination Compounds†3rd Edn., Wiley Interscience, New York, 1978.

Neves, Amanda P., Cláudia C. Barbosa, Sandro J. Greco, Maria D. Vargas, Lorenzo C. Visentin, Carlos B. Pinheiro, Antônio S. Mangrich, Jussara P. Barbosa, and Gisela L. da Costa. "Novel aminonaphthoquinone Mannich bases derived from lawsone and their copper (II) complexes: synthesis, characterization and antibacterial activity." Journal of the Brazilian Chemical Society 20, no. 4 (2009): 712-727.

Dimmock, J. R., & Kumar, P. (1997).Anticancer and cytotoxic properties of Mannich bases.Current medicinal chemistry, 4(1), 1-22.

Shahnaz, M. (2013).Synthesis, characterization of Schiffs and Mannich bases of 2, 4-thiazolidinedione derivatives and evaluation of their antioxidant activity. Journal of Drug Delivery and Therapeutics, 3(5).

Karthikeyan, M. S., Prasad, D. J., Poojary, B., SubrahmanyaBhat, K., Holla, B. S., & Kumari, N. S. (2006). Synthesis and biological activity of Schiff and Mannich bases bearing 2, 4-dichloro-5-fluorophenyl moiety.Bioorganic & medicinal chemistry, 14(22), 7482-7489.

Published

01-07-2014

How to Cite

Sivakami, M., B. Natarajan, M. Vijayachandrasekar, S. Ram Kumar Pandian, and K. Sundar. “SYNTHESIS, CHARACTERIZATION, ANTI-MICROBIAL, ANTI-CANCER, AND ANTI-OXIDANT ACTIVITY OF NOVEL 1-(NAPHTHALEIN 2-YL OXY)(PHENYL)(METHYL) THIOUREA MANNICH BASE AND ITS METAL COMPLEXES”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 6, no. 7, July 2014, pp. 59-63, https://journals.innovareacademics.in/index.php/ijpps/article/view/1194.

Issue

Section

Original Article(s)