Malaysian Journal of Analytical Sciences Vol 21 No 5 (2017): 1168 - 1175

DOI: https://doi.org/10.17576/mjas-2017-2105-21

 

 

 

SYNTHESIS, CHARACTERIZATION AND ANTIBACTERIAL ACTIVITIES OF HYDRAZONE SCHIFF BASE COMPOUNDS AND ITS DERIVATIVES

 

(Sintesis, Pencirian dan Aktiviti Antibakteria Sebatian Bes Schiff Hidrazon dan Terbitannya)

 

Ruwaida Asyikin Abu Talip1*, Meng Guan Tay1, Hashimatul Fatma Hashim2

 

1Department of Chemistry, Faculty of Resource Science and Technology

2Department of Molecular Biology, Faculty of Resource Science and Technology

Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia

 

*Corresponding author:  ruwaidaasyikinabutalip@gmail.com

 

 

Received: 21 August 2016; Accepted: 27 July 2017

 

 

Abstract

Biological activities (e.g. antibacterial) of hydrazone compound have received much attention from the synthetic chemists since last two decades. Herein, we would like to report the synthesis pathways as well as the spectroscopic characterization of three etherified hydrazone Schiff base compound, which were initiated from 2-hydroxyacetophenone. Hydrazone Schiff base compound was obtained through condensation reaction between 2-hydroxyacetophenone with benzhydrazide. Meanwhile the etherified derivatives of hydrazone Schiff base were prepared via Williamson ether synthesis under reflux condition. All the synthesized compounds were characterized using Fourier transformation infrared, UV-Vis and 1H nuclear magnetic resonance spectroscopy. In addition, the antibacterial activities of these compounds were also conducted using disc diffusion method against Bacillus cereus and Escherichia coli. The results are discussed in this present paper.

 

Keywords:  hydrazone Schiff base, etherified derivatives, antibacterial

 

Abstrak

Aktiviti biologi (contoh: antibakteria) sebatian hidrazon telah menerima banyak perhatian daripada ahli kimia sintetik sejak dua dekad yang lalu. Di sini, kami ingin melaporkan kaedah sintesis serta pencirian spektroskopi tiga hidrazon yang telah di eterifasi, dimulakan dari 2-hidroksiasetofenon. Bes-Schiff hidrazon telah diperolehi melalui tindak balas pemeluwapan antara 2-hidroksiasetofenon dengan benzihidrazida. Sementara itu, terbitan yang telah di eterifasi daripada bes Schiff hidrazon telah disediakan melalui kaedah sintesis eter Williamson di bawah keadaan refluks. Semua sebatian yang disintesis dicirikan menggunakan inframerah transformasi Fourier, spektroskopi UV-Vis dan 1H magnetik nukleus resonan. Di samping itu, aktiviti antibakteria sebatian ini juga dijalankan dengan menggunakan kaedah cakera penyebaran terhadap Bacillus cereus dan Escherichia coli. Keputusan dibincangkan dalam kajian ini.

 

Kata kunci:  bes Schiff hidrazon, terbitan yang telah dieterifasi, antibakteria

 

References

1.       Solomon, T. W. G. and Fryhle, C. B. (2011). Organic chemistry asia: John Wiley & Sons (Asia) Private Limited.

2.       Charles, D., Turner, J. H. and Redmond, C. (2005). Karyotypic profiles of women after clomiphenecitrate therapy. International Journal of Obstetrics and Gynecology, 80: 264 – 270.

3.       Alhadi, A. A., Shaker, S. A., Yehye, W. A., Mohd Ali, H. and Abdullah, M. A. (2011). Synthesis, magnetic and spectroscopic studies of Ni(II), Cu(II), Zn(II) and Cd(II) complexes of a newly Schiff base derived from 5-bromo-2-hydroxybezylidene)-3,4,5 trihydroxybenzohydrazide. Bulletin Chemical Society Ethiopia, 26(1): 95 – 101.

4.       Shelke, V. A., Jadhav, S. M., Shankarwar, S. G., Munde, A. S. and Chondhekar, T. K. (2011). Synthesis, characterization, antibacterial and antifungal studies of some transition and rare earth metal complexes of n-benzylidene-2-hydroxybenzohydrazide. Bulletin Chemical Society Ethiopia, 25(3), 381 – 391.

5.       Tan, C., Su, L., Lu, R., Xue, P., Bao, C., Liu, X. and Zhao, Y. (2006). A family of low molecular weight organogelators based on long chain substituted benzoic acid hydrazides. Journal of Molecular Liquids, 124: 32 – 36.

6.       Birnie, C. R., Malamud, D. and Schaare, R. L. (2000). Antimicrobial evaluation of n-alkyl betaines and n alkyl-n,n-dimethylamine oxides with variations in chain length. American Society for Microbiology, 44(9): 2514 – 2517.

7.       Osowole, A. A. (2012). Synthesis, spectroscopic characterization, in-vitro antibacterial and anti proliferative activities of some metal(ii) complexes of 3,4-dihydronaphthalen-1(2h) one schiff base. Experimental Clinical Sciences International Online Journal, 11: 338 – 345.

8.       Meng Guan, T., Zainab, N., Norazilawati, M. S., Siong Wan, F. and Mee Hing, T. (2011). A convenient way for the etherification of p-hydroxyacetophenone. Research Bulletin, Faculty of Resource Science and Technology, 2: 8 – 9.

9.       Prasanna, M. K. and Kumar, K. P. (2013). Synthesis, characterisation and evaluation of antitumour and antifungal activities of transition metal complexes of 4-pyridinecarboxylic acid [(2-hydroxyphenyl) methylene] hydrazide and its 5-methoxy derivative. International Journal Pharmceutical Biomedicine Science, 4(1): 24 – 29.

10.    Nam, S., Kang, S. and Chang, J. (2007). Synthesis and photopolymerization of photoreactive mesogens based on chalcone. Macromolecular Research, 15(1): 74 – 81.

11.    Joseyphus, S. and Nair, M. (2008). Antibacterial and antifungal studies on some Schiff base complexes of zinc(II). The Korean Society of Mycology, 36(2): 93 – 98.

 

 




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