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

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...

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Main Authors:	Leong, Sze Wei, Mohd Faudzi, Siti Munirah, Abas, Faridah, Mohd Aluwi, Mohd Fadhlizil Fasihi, Rullah, Kamal, Lam, Kok Wai, Abdul Bahari, Mohd Nazri, Ahmad, Syahida, Chau, Ling Tham, Shaari, Khozirah, Lajis, Nordin H.
Format:	Article
Language:	English
Published:	MDPI 2014
Subjects:	RS403 Materia Medica-Pharmaceutical Chemistry
Online Access:	http://irep.iium.edu.my/73537/ http://irep.iium.edu.my/73537/ http://irep.iium.edu.my/73537/1/Kamal%20Rullah%205.pdf

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recordtype	eprints
spelling	iium-735372019-08-07T03:35:23Z http://irep.iium.edu.my/73537/ Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents Leong, Sze Wei Mohd Faudzi, Siti Munirah Abas, Faridah Mohd Aluwi, Mohd Fadhlizil Fasihi Rullah, Kamal Lam, Kok Wai Abdul Bahari, Mohd Nazri Ahmad, Syahida Chau, Ling Tham Shaari, Khozirah Lajis, Nordin H. RS403 Materia Medica-Pharmaceutical 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 MDPI 2014-10 Article PeerReviewed application/pdf en http://irep.iium.edu.my/73537/1/Kamal%20Rullah%205.pdf 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 Chau, Ling Tham and Shaari, Khozirah and Lajis, Nordin H. (2014) Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents. Molecules, 19 (10). pp. 16058-16081. E-ISSN 1420-3049 https://www.mdpi.com/1420-3049/19/10/16058
repository_type	Digital Repository
institution_category	Local University
institution	International Islamic University Malaysia
building	IIUM Repository
collection	Online Access
language	English
topic	RS403 Materia Medica-Pharmaceutical Chemistry
spellingShingle	RS403 Materia Medica-Pharmaceutical Chemistry Leong, Sze Wei Mohd Faudzi, Siti Munirah Abas, Faridah Mohd Aluwi, Mohd Fadhlizil Fasihi Rullah, Kamal Lam, Kok Wai Abdul Bahari, Mohd Nazri Ahmad, Syahida Chau, Ling Tham Shaari, Khozirah Lajis, Nordin H. Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
description	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
format	Article
author	Leong, Sze Wei Mohd Faudzi, Siti Munirah Abas, Faridah Mohd Aluwi, Mohd Fadhlizil Fasihi Rullah, Kamal Lam, Kok Wai Abdul Bahari, Mohd Nazri Ahmad, Syahida Chau, Ling Tham Shaari, Khozirah Lajis, Nordin H.
author_facet	Leong, Sze Wei Mohd Faudzi, Siti Munirah Abas, Faridah Mohd Aluwi, Mohd Fadhlizil Fasihi Rullah, Kamal Lam, Kok Wai Abdul Bahari, Mohd Nazri Ahmad, Syahida Chau, Ling Tham Shaari, Khozirah Lajis, Nordin H.
author_sort	Leong, Sze Wei
title	Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
title_short	Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
title_full	Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
title_fullStr	Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
title_full_unstemmed	Synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
title_sort	synthesis and sar study of diarylpentanoid analogues as new anti-inflammatory agents
publisher	MDPI
publishDate	2014
url	http://irep.iium.edu.my/73537/ http://irep.iium.edu.my/73537/ http://irep.iium.edu.my/73537/1/Kamal%20Rullah%205.pdf
first_indexed	2023-09-18T21:44:16Z
last_indexed	2023-09-18T21:44:16Z
_version_	1777413344322387968

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

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