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 derivative–substituted 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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