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Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxideinhibitors

A series of forty-five 1,5-diphenylpenta-2,4-dien-1-one analogues were synthesized and evaluated for their nitric oxide (NO) inhibition activity in IFN-γ/LPS-activated RAW 264.7 cells. Compounds 3h, 7a, 7d and 7e exhibited comparable or significantly higher activity than the standard, curcumin (IC50...

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Main Authors: Mohd Faudzi, Siti Munirah Mohd Faudzi, Leong, Sze Wei, Abas, Faridah, Mohd Aluwi, Mohd Fadhlizil Fasihi, Rullah, Kamal, Lam, Kok Wai, Ahmad, Syahida, Ling Tham, Chau Ling Tham, Lajis, Nordin H.
Format: Article
Language:English
Published: Royal Society of Chemistry (RSC) 2015
Subjects:
RS403 Materia Medica-Pharmaceutical Chemistry
Online Access:http://irep.iium.edu.my/73544/1/Kamal%20Rullah%207.pdf
http://irep.iium.edu.my/73544/
https://pubs.rsc.org/en/content/articlelanding/2015/md/c4md00541d#!divAbstract
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spelling my.iium.irep.735442023-09-13T06:03:46Z http://irep.iium.edu.my/73544/ Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxideinhibitors Mohd Faudzi, Siti Munirah Mohd Faudzi Leong, Sze Wei Abas, Faridah Mohd Aluwi, Mohd Fadhlizil Fasihi Rullah, Kamal Lam, Kok Wai Ahmad, Syahida Ling Tham, Chau Ling Tham Lajis, Nordin H. RS403 Materia Medica-Pharmaceutical Chemistry A series of forty-five 1,5-diphenylpenta-2,4-dien-1-one analogues were synthesized and evaluated for their nitric oxide (NO) inhibition activity in IFN-γ/LPS-activated RAW 264.7 cells. Compounds 3h, 7a, 7d and 7e exhibited comparable or significantly higher activity than the standard, curcumin (IC50 = 14.69 ± 0.24 μM). Compound 7d, a 5-methylthiophenyl-bearing analogue, displayed the most promising NO-inhibitory activity with an IC50 value of 10.24 ± 0.62 μM. The 2D and 3D QSAR analyses performed revealed that a para-hydroxyl group on ring B and an α,β-unsaturated ketone moiety on the linker are crucial for a remarkable anti-inflammatory activity. Based on ADMET and TOPKAT analyses, compounds 3h, 7a and 7d are predicted to be nonmutagenic and to exhibit high blood–brain barrier (BBB) penetration, which indicates that they are potentially effective drug candidates for treating central nervous system (CNS) related disorders. Royal Society of Chemistry (RSC) 2015-04-20 Article PeerReviewed application/pdf en http://irep.iium.edu.my/73544/1/Kamal%20Rullah%207.pdf Mohd Faudzi, Siti Munirah Mohd Faudzi and Leong, Sze Wei and Abas, Faridah and Mohd Aluwi, Mohd Fadhlizil Fasihi and Rullah, Kamal and Lam, Kok Wai and Ahmad, Syahida and Ling Tham, Chau Ling Tham and Lajis, Nordin H. (2015) Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxideinhibitors. Medicinal Chemistry Communication, 6. pp. 1069-1080. ISSN 2040-2511 https://pubs.rsc.org/en/content/articlelanding/2015/md/c4md00541d#!divAbstract 10.1039/C4MD00541D
institution Universiti Islam Antarabangsa Malaysia
building IIUM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider International Islamic University Malaysia
content_source IIUM Repository (IREP)
url_provider http://irep.iium.edu.my/
language English
topic RS403 Materia Medica-Pharmaceutical Chemistry
spellingShingle RS403 Materia Medica-Pharmaceutical Chemistry
Mohd Faudzi, Siti Munirah Mohd Faudzi
Leong, Sze Wei
Abas, Faridah
Mohd Aluwi, Mohd Fadhlizil Fasihi
Rullah, Kamal
Lam, Kok Wai
Ahmad, Syahida
Ling Tham, Chau Ling Tham
Lajis, Nordin H.
Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxideinhibitors
description A series of forty-five 1,5-diphenylpenta-2,4-dien-1-one analogues were synthesized and evaluated for their nitric oxide (NO) inhibition activity in IFN-γ/LPS-activated RAW 264.7 cells. Compounds 3h, 7a, 7d and 7e exhibited comparable or significantly higher activity than the standard, curcumin (IC50 = 14.69 ± 0.24 μM). Compound 7d, a 5-methylthiophenyl-bearing analogue, displayed the most promising NO-inhibitory activity with an IC50 value of 10.24 ± 0.62 μM. The 2D and 3D QSAR analyses performed revealed that a para-hydroxyl group on ring B and an α,β-unsaturated ketone moiety on the linker are crucial for a remarkable anti-inflammatory activity. Based on ADMET and TOPKAT analyses, compounds 3h, 7a and 7d are predicted to be nonmutagenic and to exhibit high blood–brain barrier (BBB) penetration, which indicates that they are potentially effective drug candidates for treating central nervous system (CNS) related disorders.
format Article
author Mohd Faudzi, Siti Munirah Mohd Faudzi
Leong, Sze Wei
Abas, Faridah
Mohd Aluwi, Mohd Fadhlizil Fasihi
Rullah, Kamal
Lam, Kok Wai
Ahmad, Syahida
Ling Tham, Chau Ling Tham
Lajis, Nordin H.
author_facet Mohd Faudzi, Siti Munirah Mohd Faudzi
Leong, Sze Wei
Abas, Faridah
Mohd Aluwi, Mohd Fadhlizil Fasihi
Rullah, Kamal
Lam, Kok Wai
Ahmad, Syahida
Ling Tham, Chau Ling Tham
Lajis, Nordin H.
author_sort Mohd Faudzi, Siti Munirah Mohd Faudzi
title Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxideinhibitors
title_short Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxideinhibitors
title_full Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxideinhibitors
title_fullStr Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxideinhibitors
title_full_unstemmed Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxideinhibitors
title_sort synthesis, biological evaluation and qsar studies of diarylpentanoid analogues as potential nitric oxideinhibitors
publisher Royal Society of Chemistry (RSC)
publishDate 2015
url http://irep.iium.edu.my/73544/1/Kamal%20Rullah%207.pdf
http://irep.iium.edu.my/73544/
https://pubs.rsc.org/en/content/articlelanding/2015/md/c4md00541d#!divAbstract
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score 13.211869

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