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Synthesis and SAR study of diarylpentanoid analogues as new anti-inflammatory agents


Leong, Sze Wei and Mohd Faudzi, Siti Munirah and Abas, Faridah and Mohd Aluwi, Mohd Fadhlizil Fasihi and Rullah, Kamal and Lam, Kok Wai and Abdul Bahari, Mohd Nazri and Ahmad, Syahida and Tham, Chau Ling and Shaari, Khozirah and Lajis, Md. Nordin (2014) Synthesis and SAR study of diarylpentanoid analogues as new anti-inflammatory agents. Molecules, 19 (10). pp. 16058-16081. ISSN 1420-3049


A series of ninety-seven diarylpentanoid derivatives were synthesized and evaluated for their anti-inflammatory activity through NO suppression assay using interferone gamma (IFN-γ)/lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Twelve compounds (9, 25, 28, 43, 63, 64, 81, 83, 84, 86, 88 and 97) exhibited greater or similar NO inhibitory activity in comparison with curcumin (14.7 ± 0.2 µM), notably compounds 88 and 97, which demonstrated the most significant NO suppression activity with IC50 values of 4.9 ± 0.3 µM and 9.6 ± 0.5 µM, respectively. A structure–activity relationship (SAR) study revealed that the presence of a hydroxyl group in both aromatic rings is critical for bioactivity of these molecules. With the exception of the polyphenolic derivatives, low electron density in ring-A and high electron density in ring-B are important for enhancing NO inhibition. Meanwhile, pharmacophore mapping showed that hydroxyl substituents at both meta- and para-positions of ring-B could be the marker for highly active diarylpentanoid derivatives.

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Additional Metadata

Item Type: Article
Divisions: Faculty of Biotechnology and Biomolecular Sciences
Faculty of Food Science and Technology
Faculty of Medicine and Health Science
Faculty of Science
Institute of Bioscience
DOI Number: https://doi.org/10.3390/molecules191016058
Publisher: MDPI
Keywords: Anti-inflammatory; Diarylpentanoid; RAW 264.7; Curcumin; SAR; Pharmacophore
Depositing User: Nurul Ainie Mokhtar
Date Deposited: 14 Jan 2016 01:41
Last Modified: 07 Feb 2018 06:23
Altmetrics: http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.3390/molecules191016058
URI: http://psasir.upm.edu.my/id/eprint/35571
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