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...
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI
2014
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| Online Access: | http://psasir.upm.edu.my/id/eprint/35571/1/Synthesis%20and%20Sar%20Study%20of%20Diarylpentanoid%20Analogues%20as%20New.pdf |
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| 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 Tham, Chau Ling Shaari, Khozirah Lajis, Md. Nordin |
| 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 Tham, Chau Ling Shaari, Khozirah Lajis, Md. Nordin |
| author_sort | Leong, Sze Wei |
| collection | UPM |
| 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. |
| first_indexed | 2024-03-06T08:32:44Z |
| format | Article |
| id | upm.eprints-35571 |
| institution | Universiti Putra Malaysia |
| language | English |
| last_indexed | 2024-03-06T08:32:44Z |
| publishDate | 2014 |
| publisher | MDPI |
| record_format | dspace |
| spelling | upm.eprints-355712018-02-07T06:23:29Z http://psasir.upm.edu.my/id/eprint/35571/ 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 Tham, Chau Ling Shaari, Khozirah Lajis, Md. Nordin 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 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/35571/1/Synthesis%20and%20Sar%20Study%20of%20Diarylpentanoid%20Analogues%20as%20New.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 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 http://www.mdpi.com/1420-3049/19/10/16058 10.3390/molecules191016058 |
| spellingShingle | 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 Tham, Chau Ling Shaari, Khozirah Lajis, Md. Nordin Synthesis and SAR study of diarylpentanoid analogues as new anti-inflammatory agents |
| title | 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_short | 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 |
| url | http://psasir.upm.edu.my/id/eprint/35571/1/Synthesis%20and%20Sar%20Study%20of%20Diarylpentanoid%20Analogues%20as%20New.pdf |
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