Synthesis and Characterization of Schiff Base 1-Amino-4-methylpiperazine Derivatives

Synthesis and Characterization of Schiff Base 1-Amino-4-methylpiperazine Derivatives

In this study, potentially biological active new Schiff bases were synthesized in good yield from 1-amino-4methylpiperazine and aromatic aldehydes as a 3-nitro-benzaldehyde, 4-fluoro-benzaldehyde, 3,4,5trimethoxybenzaldehyde, 3,4-dichlorobenzaldehyde, 4-diethylaminobenzaldehyde, 2,5-dimethoxybenzaldehyde and 5-nitro-2-furaldehyde and structure of the synthesized compounds were elucidated by FTIR, LC-MS, 1HNMR and 13C-NMR techniques.

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  • [1] Qin W., Long S., Panunzio M., and Biondi S., Schiff Bases: A Short Survey on an Evergreen Chemistry Tool, Molecules, 2013; 18, 12264-12289.
  • [2] Silva C. M., Silva Daniel L., Modolo L. V., Alves R. B., de Resende M. A., Martins C. V.B., Fatima A., Schiff bases: A short review of their antimicrobial activities, Journal of Advanced Research, 2011; 2, 1-8.
  • [3] Brodowska K., Lodyga-Chruscinska E., Schiff bases - interesting range of applications in various fields of science, Chemik, 2014; 68, 2, 129-134.
  • [4] Shabbir M., Akhter Z., Ahmad I., Ahmed S., Ismail H., Bushra M., McKeec V., Bolted M., Synthesis, characterization, biological and electrochemical evaluation of novel ether based on donor bidentate Schiff bases, Journal of Molecular Structure, 2016; Vol. 1116, 84-92.
  • [5] Sılku P., Özkınalı S., Öztürk Z., Asan A., Köse D. A., Synthesis of novel Schiff Bases containing acryloyl moiety and the investigation of spectroscopic and electrochemical properties, Journal of Molecular Structure, 2016; 1116, 72- 83.
  • [6] Reddy K. K., Rao S., Sreedhar R. B., Synthesis and Characterization and Biological Activities of Hydrazones, International Journal of Innovative Research in Science, Engineering and Technology, 2015; Vol. 4, Issue 1, 18944- 18952.
  • [7] Wang L., Wang Y., Hou Z., Liu Y., Synthesis and Fluorescence Property of novel Zn2+ Schiff base Complex, Advanced Materials Research, 2012; Vols. 535-537, 1237- 1240.
  • [8] Zoubi W. A., Biological Activities of Schiff Bases and Their Complexes: A Review of Recent Works, International Journal of Organic Chemistry, 2013; 3, 73-95.
  • [9] Gwaram N. S., Ali M. H., Khaledi H., Abdulla A. M., A. Hamid A. Hadi., Lin T. K., Ching C. L., and Ooi C. L., Antibacterial Evaluation of Some Schiff Bases Derived from 2-Acetylpyridine and Their Metal Complexes, Molecules, 2012; 17, 5952-5971.
  • [10] Arulmurugan S., Kavitha H. P. and Venkatraman B.R., Biological Activities of Schiff Base and its Complexes: A Review, Vol.3, Rasayan J.Chem. 2010; No.3, 385-410.
  • [11] Nichols C. J., Automated Combinatorial Chemistry in the Organic Chemistry Majors Laboratory, Journal of Chemical Education, 2010; Vol. 87, No. 1, 87-90.
  • [12] Govindasami T., Pandey A., Palanivelu N., Pandey A., Synthesis, Characterization and Antibacterial Activity of Biologically Important Vanillin Related Hydrazone Derivatives, International Journal of Organic Chemistry, 2011; 1, 71-77.
  • [13] Dubrovskiy A. V. and Larock R. C., Synthesis of o-(Dimethylamino)aryl Ketones, Acridones, Acridinium Salts, and 1H-Indazoles by the Reaction of Hydrazones and Arynes, J. Org. Chem. 2012; 77, 11232-11256.
  • [14] Rollas S., and Küçükgüzel Ş. G., Biological Activities of Hydrazone Derivatives, Molecules, 2007; 12, 1910-1939.
  • [15] Li-na Z., Hui-liang Z., Long, Y., Qi-lin Hu, Synthesis and characterization of 1-amino-4-methylpiperazine aromatic aldehyde Schiff base, Huaxue Shijie, 2011; 52(2), 113-115.
  • [16] Koçyiğit-Kaymakçıoğlu B., Elçin O., Seda U., Fatma K., Nathaly S., Sevim R., Dimoglo A. Synthesis and characterization of novel hydrazide hydrazones and the study of their structure-antituberculosis activity, European Journal of Medicinal Chemistry, 2006; 41, 1253- 1261.
  • [17] Foks H., Pancechowska-Ksepko D., Kedzia A., Zwolska Z., Janowiec M., Augustynowicz-Kopec E., Synthesis and antibacterial activity of 1H-pyrazolo[3,4- b]pyrazine and -pyridine derivatives, Il Farmaco, 2005; 60, 513-517.
  • [18] Mizufune H., Yamamoto H., Nakamura M., Miki S., A new efficient synthetic strategy for N- (dialkylamino)azacycle as a tetrasubstituted hydrazine derivative using sodium triacyloxyborohydride, Tetrahedron, 2008; 64, 6275-6280.
  • [19] Kharb R., Bansal K., Sharma A. K., A valuable insight into recent advances on antimicrobial activity of piperazine derivatives, Der Pharma Chemica, 2012; 4(6):2470-2488.
  • [20] Kavitha C. N., Jasinski J. P., Anderson B. J., Yathirajana H.S. and Kaura M., 4-Methyl-N-(4- nitrobenzylidene)-piperazin-1-amine, Acta Cryst., 2013; E69, o1687-o1688.
  • [21] Kavitha C. N., Jasinski J. P., Kaur M., Yathirajan H.S. (4-Methylpiperazin-1-yl)(2,3,4- trimethoxybenzylidene)amine, Acta Cryst. 2014; E70, o500.
  • [22] Pettersson S., P_rez-Nueno V. I., Ros-Blanco L., Bellacasa R. P. L., Rabal O. M., Batllori X., Clotet B., ClotetCodina I., Armand-Ugon M., Este, J., Borrell J., and Teixid J., Discovery of Novel Non-Cyclam Polynitrogenated CXCR4 Coreceptor Inhibitors, ChemMedChem, 2008; 3, 1549 - 1557.
  • [23] Govindasami T., Pandey A., Palanivelu N., Pandey A., Synthesis, Characterization and Antibacterial Activity of Biologically Important Vanillin Related Hydrazone Derivatives, International Journal of Organic Chemistry, 2011; 1, 71-77.
  • [24] Guo M. L., 2-[(4-Methylpiperazin-1- yl)iminomethyl]phenol, Acta Cryst., 2007; E63, o1788- o1789.
  • [25] Vladimir V., Holubek J., Svatek Emil and Provita M., Synthesis of 4-methoxyphenoxyacetic and 3,4,5- trimethoxyphenoxyacetic acid amides and Hydrazides as potential neurotropic and cardiovascular agents, Collection Czechoslovak Chern. Commun. 1987; Vol. 521, 3013-3023.
  • [26] Riva S., and Silvestri L. C., Rifamycins: A General View, 199-224.
  • [27] Tandel, D. C., Desai C.M., Patel D., Naik B., Marjadi S., Some antimicrobial agents, Oriental Journal of Chemistry, 17(3), 2001; 519-520.
  • [28] Vardanyan R.S. and Hruby V. J., Synthesis of Essential Drugs, 2006; 486-487 pp.