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Open AccessArticle

Synthesis and Sar Study of Diarylpentanoid Analogues as New Anti-Inflammatory Agents

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Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
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Department of Food Science, Faculty of Food Science and Technology, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
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Drug and Herbal Research Centre Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abd. Aziz, 50300 Kuala Lumpur, Malaysia
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Department of Biochemistry, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
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Department of Biomedical Science, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
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Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
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Al-Moalim BinLaden Chair for Scientific Miracles of Prophetic Medicine, Scientific Chairs Unit, Taibah University, P.O. Box 30001, Madinah al Munawarah 41311, Saudi Arabia
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Authors to whom correspondence should be addressed.
Molecules 2014, 19(10), 16058-16081; https://doi.org/10.3390/molecules191016058
Received: 8 August 2014 / Revised: 15 September 2014 / Accepted: 18 September 2014 / Published: 9 October 2014
(This article belongs to the Section Medicinal Chemistry)
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. View Full-Text
Keywords: anti-inflammatory; diarylpentanoid; RAW 264.7; curcumin; SAR; pharmacophore anti-inflammatory; diarylpentanoid; RAW 264.7; curcumin; SAR; pharmacophore
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Leong, S.W.; Faudzi, S.M.M.; Abas, F.; Aluwi, M.F.F.M.; Rullah, K.; Wai, L.K.; Bahari, M.N.A.; Ahmad, S.; Tham, C.L.; Shaari, K.; Lajis, N.H. Synthesis and Sar Study of Diarylpentanoid Analogues as New Anti-Inflammatory Agents. Molecules 2014, 19, 16058-16081.

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