Malaysian Journal of Analytical Sciences Vol 21 No 5 (2017): 1183 - 1194

DOI: https://doi.org/10.17576/mjas-2017-2105-23

 

 

 

SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF AZO AND ASPIRIN-AZO DERIVATIVES

 

(Sintesis dan Aktiviti Antibakteria Terhadap Azo dan Terbitan Azo-Aspirin)

 

Zainab Ngaini and Ho Boon Kui*

 

Department of Chemistry,

Faculty of Resource Science and Technology,

Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia

 

*Corresponding author:  boonkui98@hotmail.com

 

 

Received: 21 August 2016; Accepted: 27 July 2017

 

 

Abstract

A series of azo derivatives (1a-e) were synthesized via coupling reaction with of overall yield 58 – 72% while aspirin-azo derivatives (2a-e) were prepared by esterification reaction of aspirin and azo derivatives (1a-e) with overall yield 38 – 75%. In this study, the structures of synthesized compounds were characterized using elemental analysis (CHN), nuclear magnetic resonance (1H NMR and 13C NMR) and Fourier Transform Infrared (FTIR) spectroscopy. The synthesized compounds were tested on antibacterial activity against Escherichia coli ATCC 25922 and Staphylococcus aureus S48/81 via turbidimetric kinetic method. The azo derivativesubstituted fluorine, 1d showed the highest antibacterial activities against Escherichia coli ATCC 25922 and Staphylococcus aureus S48/81 compared with other synthesized compounds. However, synthesized aspirin–azo derivatives (2a-e) showed weak antibacterial activity against tested bacteria due to bulky molecular structure thus hindered the penetration into bacterial cell wall. 

 

Keywords: aspirin, azo derivatives, turbidimetric kinetic, Escherichia coli ATCC 25922, Staphylococcus aureus S48/81

 

Abstrak

Satu siri terbitan azo (1a-e) telah dihasilkan melalui tindak balas gandingan dengan hasil keseluruhan 58 – 72% dan terbitan azo-aspirin (2a-e) telah disediakan melalui tindak balas esterifikasi aspirin dan terbitan azo (1a-e) dengan hasil keseluruhan 38 – 75%. Dalam kajian ini, struktur sebatian yang dihasilkan dicirikan menggunakan analisis unsur (CHN), resonans magnetik nukleus (1H NMR dan 13C NMR) dan spektroskopi inframerah transformasi Fourier . Kesemua sebatian yang dihasilkan telah diuji pada aktiviti anti-bakteria terhadap Escherichia coli ATCC 25922 dan Staphylococcus aureus S48 / 81 melalui kaedah kinetik turbidimetrik. Terbitan azo tertukarganti fluorin 1d menunjukkan aktiviti antibakteria tertinggi terhadap Escherichia coli ATCC 25922 dan Staphylococcus aureus S48/81 berbanding dengan sebatian lain. Walau bagaimanapun, terbitan azo aspirin (2a-e) menunjukkan aktiviti anti-bakteria yang lemah terhadap bakteria diuji disebabkan oleh struktur molekul yang besar itu telah menghalang penembusan ke dalam dinding sel bakteria.

 

Kata kunci:  aspirin, terbitan azo, kinetik turbidimetrik, Escherichia coli ATCC 25922, Staphylococcus aureus S48/81

 

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