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Vol. 27 No. 9 (2015): Vol 27 Issue 9

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Synthesis of Ibuprofen Derivatives with Improved Antibacterial Activity

https://doi.org/10.14233/ajchem.2015.18498
Shumaila Kiran
Department of Applied Chemistry and Biochemistry, Government College University, Faisalabad-38000, Pakistan
Shagufta Kamal
Department of Applied Chemistry and Biochemistry, Government College University, Faisalabad-38000, Pakistan
Nosheen Aslam
Department of Applied Chemistry and Biochemistry, Government College University, Faisalabad-38000, Pakistan
Abdullah Ijaz Hussain
Department of Applied Chemistry and Biochemistry, Government College University, Faisalabad-38000, Pakistan
Abdul Ghaffar
Department of Applied Chemistry and Biochemistry, Government College University, Faisalabad-38000, Pakistan
Ismat Bibi
Department of Chemistry, Islamia University, Bhawalpur-63100, Pakistan
Amna Kamal
Department of Chemistry, University of Agriculture, Faisalabad-38000, Pakistan
Bushra Munir
Department of Applied Chemistry and Biochemistry, Government College University, Faisalabad-38000, Pakistan
Neelam Sultan
Department of Applied Chemistry and Biochemistry, Government College University, Faisalabad-38000, Pakistan

Corresponding Author(s) : Shagufta Kamal

shaguftakamal81@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 9 (2015): Vol 27 Issue 9

Abstract

A new series of ibuprofen derivatives i.e., (S)-ibuprofen amide, (S)-4-(2-(4-isobutylphenyl)propanamido)benzoic acid, (S)-3-(4-isobutylphenyl)butan-2-one compound with morpholine, (S)-2-(4-isobutylphenyl)-N-(4-nitrophenyl)propanamide and (S)-3-hydroxy-5-(2-(4-isobutylphenyl)propylamino benzoic acid have been synthesized by treating commercially available 2-(4-isobutyl-phenyl)propionic acid (ibuprofen) with thionyl chloride to get 2-(4-isobutyl-phenyl)propionyl chloride. Acid chloride was further reacted with different amines to get ibuprofen amides. The structures of all these compounds were confirmed on the basis of their analytical and spectral data. FTIR and elemental analysis were performed to characterize the synthesized compounds. Chemical stability studies revealed that amide derivatives were chemically stable at pH 1.2-6.8. Disc diffusion and micro-dilution assays were used to evaluate the antibacterial potential of synthesized ibuprofen derivatives against Gram positive i.e., Bacillus subtilis and Gram negative strains i.e., Escherichia coli. The amide derivatives of ibuprofen exhibited stronger inhibitory effect against tested bacteria than ester derivatives. MIC values of all derivatives were in the range of 2-20 mg/mL. Results suggested that amide derivative of ibuprofen has more potential as antimicrobial agent it may find its application against infectious diseases.

Keywords

Ibuprofen derivatives Microbial assay Anti-inflammatory Analgesic
Kiran, S., Kamal, S., Aslam, N., Ijaz Hussain, A., Ghaffar, A., Bibi, I., … Sultan, N. (2015). Synthesis of Ibuprofen Derivatives with Improved Antibacterial Activity. Asian Journal of Chemistry, 27(9), 3259–3262. https://doi.org/10.14233/ajchem.2015.18498
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