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/ http://irep.iium.edu.my/73544/ http://irep.iium.edu.my/73544/ http://irep.iium.edu.my/73544/1/Kamal%20Rullah%207.pdf

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recordtype	eprints
spelling	iium-735442019-09-13T01:08:28Z 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
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 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/ http://irep.iium.edu.my/73544/ http://irep.iium.edu.my/73544/ http://irep.iium.edu.my/73544/1/Kamal%20Rullah%207.pdf
first_indexed	2023-09-18T21:44:16Z
last_indexed	2023-09-18T21:44:16Z
_version_	1777413344904347648

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

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