Next Article in Journal
Studies Regarding As(V) Adsorption from Underground Water by Fe-XAD8-DEHPA Impregnated Resin. Equilibrium Sorption and Fixed-Bed Column Tests
Previous Article in Journal
Characterization and Quantification of the Compounds of the Ethanolic Extract from Caesalpinia ferrea Stem Bark and Evaluation of Their Mutagenic Activity
Article Menu
Issue 10 (October) cover image

Export Article

Open AccessArticle
Molecules 2014, 19(10), 16058-16081; doi:10.3390/molecules191016058

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

1
Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
2
Department of Food Science, Faculty of Food Science and Technology, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
3
Drug and Herbal Research Centre Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abd. Aziz, 50300 Kuala Lumpur, Malaysia
4
Department of Biochemistry, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
5
Department of Biomedical Science, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
6
Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia
7
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
*
Authors to whom correspondence should be addressed.
Received: 8 August 2014 / Revised: 15 September 2014 / Accepted: 18 September 2014 / Published: 9 October 2014
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [1343 KB, uploaded 9 October 2014]   |  

Abstract

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
Figures

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top