Malaysian Journal of Analytical Sciences Vol 21 No 5 (2017): 1195 - 1202

DOI: https://doi.org/10.17576/mjas-2017-2105-24

 

 

 

SYNTHESIS, MODIFICATION, CHARACTERIZATION AND BIOLOGICAL ACTIVITY OF 3-HYDROXYBENZALDEHYDESALICYLHYDRAZIDE

 

(Sintesis, Modifikasi, Pencirian dan Aktiviti Biologi 3-Hidroksibenzaldehidesalisilhidrazida)

 

Nornadia Jasin¹*, 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:  nornadiajasin@gmail.com

 

 

Received: 21 August 2016; Accepted: 27 July 2017

 

 

Abstract

A series of hydrazone Schiff base (compounds S, S8, S10 and S12) were synthesized by condensation reaction of salicylhydrazide with 3-hydroxybenzaldehyde, 3-(octyloxy)benzaldehyde, 3-(decyloxy)benzaldehyde and 3-(dodecyloxy) benzaldehyde, respectively. Herein, the addition of alkane numbers are reported using suscessful Williamson etherification method by reacting 3-hydroxybenzaldehyde with bromooctane, bromodecane and bromododecane, respectively. All compounds were characterised using Fourier Transform Infrared and ¹H Nuclear Mangnetic Resonance spectroscopic. The compounds were assayed to antibacterial activity against Gram-positive and Gram-negative bacteria using Bacillus cereus and Escherichia coli by disc diffusion method. Interestingly, among the compounds tested S8 showed a strong inhibition against Escherichia coli and none of the compounds tested show significant result against Bacillus cereus.

 

Keywords:  3-hydroxybenzaldehyde, Williamson etherification, hydrazone Schiff base, antibacterial activity

 

Abstrak

Satu siri bes Schiff hidrazon (sebatian S, S8, S10 dan S12) telah disintesis mengunakan tindakbalas pemeluwapan oleh salisilhidrazida dengan 3-hidroksibenzaldehid, 3-(oktiloksi)benzaldehid, 3-(deciloksi)benzaldehid dan 3-(dodeciloksi) benzaldehid. Di sini, penambahan nombor alkana juga telah dilaporkan menggunakan kaedah pengeteran Williamson yang berjaya daripada tindak balas 3 -hidroksibenzaldehid dengan bromooktana, bromodekana dan bromododekana. Semua sebatian telah dicirikan menggunakan  spektroskopi inframerah transformasi Fourier dan ¹H nukleus magnetik resonan. Sebatian yang terhasil telah diuji dengan aktiviti antibakteria terhadap bakteria Gram-positif dan Gram- negatif menggunakan Bacillus cereus dan Escherichia coli dengan kaedah cakera resapan. Menariknya, diantara sebatian yang telah diuji, S8 menunjukkan perencatan yang kuat terhadap Escherichia coli dan tiada sebatian menunjukkan hasil yang ketara terhadap Bacillus cereus.

 

Kata kunci:  3- hidroksibenzaldehid, pengeteran Williamson, bes Schiff hidrazon, aktiviti antibakteria

 

References

1.       Khanmohammadi, H., Abnosi, M. H., Hosseinzadeh, A. And Erfantalab, M. (2008).  Synthesis, biological and computational study of new Schiff base hydrazones bearing 3-(4-pyridine)-5-mercapto-1,2,4-triazole moiety. Spectrochimica Acta Part A, 71: 1474 – 1480.

2.       Hearn, M. J., Cynamon, M. H., Chen, M. F., Coppins, R., Davis, J., Kang, H. J. O., Noble, A., Sekine, B. T., Terrot, M. S., Trombino, D., Thai, M., Webster, E. R. and Wilson, R. (2009). Preparation and antitubercular activities in vitro and in vivo of novel Schiff base of isoniazid. European Journal of Medicinal Chemistry, 44: 4169 – 4178.

3.       Walcourt, A., Loyevsky, M., Lovejoy, D. B., Gordeuk, V. R. and Richardson, D. R. (2004). Novel aroylhydrazone and thiosemicarbazone iron chelators with anti-malarial activity against chloroquine-resistant and –sensitive parasites. The International Journal of Biochemistry & Cell Biology, 36: 401 –407.

4.       Mishra, N., Poonia, K. and Kumar, D. (2013). An overview of biological aspects of Schiff base metal complexes. International Journal of Advancements in Research & Technology, 2(8): 52 – 66.

5.       Devinsky, F. and Gorrod, J. W. (1987). Microsomal N-oxidation of long chain N,N-dimethylalkylamines: Quantitative structure-activity relationships. European Journal of Drug Metabolism and Pharmacokinetics, 12: 267 – 273.

6.       Park, K. D., Park, Y. S., Cho, S. J., Sun, W. S., Kim, S. H., Jung, D. H. and Kim, J. H. (2004). Antimicrobial activity of 3-O-acyl-(-)-epicatechin and 3-O-acyl-(+)-catechin derivatives. Planta Medica, 70: 272 – 276.

7.       Tay, M. G., Ngaini, Z., Sarih, N. M., Foo, S.W. and Tiong, M. H. (2011). A convenient way for the etherification of p-hydroxyacetophenone. Research Bulletin, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak: pp. 1 – 3.