Nitric oxide inhibitory activity and antioxidant evaluations of 2-benzoyl-6-benzylidenecyclohexanone analogs, a novel series of curcuminoid and diarylpentanoid derivatives

Sze Wei Leong, Siti Munirah Mohd Faudzi, Faridah Abas, Mohd Fadhlizil Fasihi Mohd Aluwi, Kamal Rullah, Kok Wai Lam, Mohd Nazri Abdul Bahari, Syahida Ahmad, Chau Ling Tham, Khozirah Shaari, Nordin H. Lajis

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Abstract A series of twenty-four 2-benzoyl-6-benzylidenecyclohexanone analogs were synthesized and evaluated for their nitric oxide inhibition and antioxidant activity. Six compounds (3, 8, 10, 17, 18 and 19) were found to exhibit significant NO inhibitory activity in LPS/IFN-induced RAW 264.7 macrophages, of which compound 10 demonstrated the highest activity with the IC<inf>50</inf> value of 4.2 ± 0.2 μM. Furthermore, two compounds (10 and 17) displayed antioxidant activity upon both the DPPH scavenging and FRAP analyses. However, none of the 2-benzoyl-6-benzylidenecyclohexanone analogs significantly scavenged NO radical. Structure-activity comparison suggested that 3,4-dihydroxylphenyl ring is crucial for bioactivities of the 2-benzoyl-6-benzylidenecyclohexanone analogs. The results from this study and the reports from previous studies indicated that compound 10 could be a candidate for further investigation on its potential as a new anti-inflammatory agent.

Original languageEnglish
Article number22746
Pages (from-to)3330-3337
Number of pages8
JournalBioorganic and Medicinal Chemistry Letters
Volume25
Issue number16
DOIs
Publication statusPublished - 3 Jul 2015

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Nitric Oxide
Antioxidants
Derivatives
Macrophages
Scavenging
Bioactivity
Inhibitory Concentration 50
Anti-Inflammatory Agents
compound 17

Keywords

  • 2-Benzoyl-6-benzylidenecyclohexanone
  • Anti-inflammatory
  • Antioxidant
  • RAW 264.7
  • Stability

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

Nitric oxide inhibitory activity and antioxidant evaluations of 2-benzoyl-6-benzylidenecyclohexanone analogs, a novel series of curcuminoid and diarylpentanoid derivatives. / 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, Nordin H.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 25, No. 16, 22746, 03.07.2015, p. 3330-3337.

Research output: Contribution to journalArticle

Leong, SW, Mohd Faudzi, SM, Abas, F, Mohd Aluwi, MFF, Rullah, K, Lam, KW, Abdul Bahari, MN, Ahmad, S, Tham, CL, Shaari, K & Lajis, NH 2015, 'Nitric oxide inhibitory activity and antioxidant evaluations of 2-benzoyl-6-benzylidenecyclohexanone analogs, a novel series of curcuminoid and diarylpentanoid derivatives', Bioorganic and Medicinal Chemistry Letters, vol. 25, no. 16, 22746, pp. 3330-3337. https://doi.org/10.1016/j.bmcl.2015.05.056
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, Nordin H. / Nitric oxide inhibitory activity and antioxidant evaluations of 2-benzoyl-6-benzylidenecyclohexanone analogs, a novel series of curcuminoid and diarylpentanoid derivatives. In: Bioorganic and Medicinal Chemistry Letters. 2015 ; Vol. 25, No. 16. pp. 3330-3337.
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AU - Abas, Faridah

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AU - Rullah, Kamal

AU - Lam, Kok Wai

AU - Abdul Bahari, Mohd Nazri

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AU - Shaari, Khozirah

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AB - Abstract A series of twenty-four 2-benzoyl-6-benzylidenecyclohexanone analogs were synthesized and evaluated for their nitric oxide inhibition and antioxidant activity. Six compounds (3, 8, 10, 17, 18 and 19) were found to exhibit significant NO inhibitory activity in LPS/IFN-induced RAW 264.7 macrophages, of which compound 10 demonstrated the highest activity with the IC50 value of 4.2 ± 0.2 μM. Furthermore, two compounds (10 and 17) displayed antioxidant activity upon both the DPPH scavenging and FRAP analyses. However, none of the 2-benzoyl-6-benzylidenecyclohexanone analogs significantly scavenged NO radical. Structure-activity comparison suggested that 3,4-dihydroxylphenyl ring is crucial for bioactivities of the 2-benzoyl-6-benzylidenecyclohexanone analogs. The results from this study and the reports from previous studies indicated that compound 10 could be a candidate for further investigation on its potential as a new anti-inflammatory agent.

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