Synthesis and evaluation of biological properties of benzylideneacetophenone derivatives

Oh, Seikwan; Jang, Soyong; Kim, Dong-Hyun; Han, Inn Oc; Jung, Jaehan

doi:10.1007/bf02969418

Cited by 19 publications

(19 citation statements)

References 15 publications

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“…The biological activities of benzylideneacetophenone derivatives were evaluated for their freeradical scavenging activities, suppression of LPS-induced NO generation, and antiexcitotoxic effects in in vitro. Favorable scavenging ratios, in the 50% range at a concentration of approximately 50 M, were found in all synthesized compounds (JC1-JC6) in the previous results (Oh et al, 2006).…”

supporting

confidence: 70%

“…The conjugated 1,4-enones containing a phenyl ring belongs to an important class of natural chalcones that have shown a wide range of biological activities (Yamazaki et al, 2000). It has been reported that yakuchinone B showed several significant biological activities, such as anti-inflammatory (Srimal and Dhawan, 1973), antitumor (Samaha et al, 1997), antiviral (Ninomiya et al, 1990), and neuroprotective effects (Oh et al, 2006). Because of their interesting structural features and characteristic therapeutic effects, we decided to design and develop novel compounds such as JC1 to JC5.…”

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confidence: 99%

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The Neuroprotective Effects of Benzylideneacetophenone Derivatives on Excitotoxicity and Inflammation via Phosphorylated Janus Tyrosine Kinase 2/Phosphorylated Signal Transducer and Activator of Transcription 3 and Mitogen-Activated Protein K Pathways

Jang

Jung²,

Kim

et al. 2008

J Pharmacol Exp Ther

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To search for new neuroprotective compounds, novel benzylideneacetophenone compounds (JCI, (3E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one; JC2, (1E)-1-(4-hydroxy-3-methoxyphenyl)hept-1-en-3-one; JC3, (2E)-3-(4-hydroxy-3-methoxyphenyl)phenylpro-2-en-l-one; JC4, (1E)-1-(4-hydroxy-3-methoxyphenyl)-5-phenylpent-1-en-3-one; JC5, (1E)-3-(4-hydroxy-3-methoxyphenyl)-6-phenylhex-1-en-3-one; JC6, (1E)-1-(4-hydroxy-3-methoxyphenyl]-7-phenylhept-1-en-3-one) were synthesized, and their potential to prevent neurotoxicities were evaluated. All compounds (JC1-JC6) showed considerable effect on free radical scavenging, the inhibition of glutamate-induced neurotoxicity in cortical cells, and the suppression of lipopolysaccharide (LPS)-induced nitric oxide (NO) generation in microglia. (2E)-3-(4-Hydroxy-3-methoxyphenyl)-phenylpro-2-en-1-one (JC3) exhibited the most potent neuroprotective effect in ischemia model using organotypic hippocampal culture and middle cerebral artery occlusion (MCAO). Based on the above-mentioned results, the mechanisms underlying the biological activity of JC3, which exhibited potent antiexcitotoxic and anti-inflammatory effects, were determined using cortical neuronal cells and microglia. Compound JC3 exerted a neuroprotective effect on oxygen-glucose deprivation-and hydrogen peroxide-induced cytotoxicity in cultured cortical cells. In addition, it suppressed the generation of NO, proinflammatory cytokines, and reactive oxygen species in LPS-treated microglial cells. It also suppressed the activation of phosphorylated Janus tyrosine kinase 2/phosphorylated signal transducer and activator of transcription 3 and mitogenactivated protein kinase (MAPK) in activated microglia and in cortex and striatum after 3 days of the MCAO in mice. These results demonstrated that JC3 might affect a set of intracellular signaling cascades, including the Janus tyrosine kinase/ signal transducers and activators of transcription and MAPK pathways. This study suggests that benzylideneacetophenone derivative could be useful antineurotoxic agents.The major pathogenic mechanisms of stroke include excitotoxicity, production of reactive free radicals, inflammation, and apoptosis (Mergenthaler et al., 2004). Activation of glutamate receptors, through the attendant failure of ion homeostasis and increase in intracellular Ca 2ϩ concentration, Article, publication date, and citation information can be found at

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confidence: 70%

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confidence: 99%

The Neuroprotective Effects of Benzylideneacetophenone Derivatives on Excitotoxicity and Inflammation via Phosphorylated Janus Tyrosine Kinase 2/Phosphorylated Signal Transducer and Activator of Transcription 3 and Mitogen-Activated Protein K Pathways

Jang

Jung²,

Kim

et al. 2008

J Pharmacol Exp Ther

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“…The importance of COX-2 in mediating Parkinson disease (PD) has been suggested in the previous studies reporting that COX-2 selective inhibitors or genetic knockout of COX-2 reduced MPTP-induced dopaminergic neurotoxicity in a mouse model of PD (Wang et al, 2005;Vijitruth et al, 2006). A previous in vitro study showed that JC3, a novel benzylideneacetophenone compound, showed biological activities of free radical scavenging, the suppression of lipopolysaccharide (LPS)-induced nitric oxide (NO) generation, and anti-excitotoxicity in cortical culture neurons (Oh et al, 2006). The results proved that JC3 has potent antioxidant and anti-inflammatory effects.…”

Section: Discussionmentioning

confidence: 93%

“…Astroglial and microglial activation in the SNpc play a crucial role in the pathology of many neurodegenerative diseases, including PD, and is thought to be associated with the expression of COX-2 (Kitamura et al, 1994;Matsuura et al, 1997;Oh et al, 2006). Microglia, the resident immune cells in the brain, play a pivotal role in the detec- tion of invading pathogens, host defense, and tissue repair (Kohutnicka et al, 1998;Aloisi, 1999).…”

Section: Discussionmentioning

confidence: 98%

“…The novel benzylideneacetophenones were examined for free radical scavenging, suppression of lipopolysaccharide (LPS)-induced nitric oxide (NO) generation, and anti-excitotoxicity in cultured cortical neurons (Oh et al, 2006). JC3 [(2E)-3-(4-hydroxy-3-methoxyphenyl) phenylpro-2-en-1-one] had more potent antioxidant and anti-inflammatory effects than the other compounds.…”

Section: Introductionmentioning

confidence: 99%

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Neuroprotective effect of benzylideneacetophenone derivative on the MPTP model of neurodegeneration in mice

et al. 2008

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In this study, we investigated the neuroprotective effect of a benzylideneacetophenone derivative, JC3, in a mouse model of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced Parkinson's disease (PD). C57BL/6 mice were treated with MPTP (30 mg/kg, i.p.) for 5 consecutive days. JC3 (10 mg/kg, i.p.) treatment was initiated 2 h after the first administration of MPTP and then at 24-h intervals for 3 consecutive days. The mice were sacrificed for analyses 7 days after the last MPTP injection. Immunohistochemistry and Western blot were used to determine the expression levels of tyrosine hydroxylase (TH), dopamine transporter (DAT), OX-42 (a marker of microglial activation), and glial fibrillary acid protein (GFAP, a marker of astrocyte activation) in the substantia nigra (SN) and striatum (ST). The results of these experiments demonstrated that JC3 restored the decreased TH-immunoreactivity (IR) and DAT and JC3 attenuated the increase in OX-42, GFAP, and COX-2 on the SN and ST on day 7 post-MPTP injection. These results suggest that JC3 can be a neuroprotective agent in an MPTP-induced model of PD.

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Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: A Reactivity Study towards O‐, N‐, S‐, and C‐Nucleophiles

Roman¹,

Monbaliu²,

Coen³

et al. 2014

Eur J Org Chem

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A versatile route for the conversion of ferulic acid into biologically relevant molecules is presented. The compatibility of a number of protection and activation strategies with the 1,2‐addition of a variety of O‐, N‐, S‐, and C‐nucleophiles to ferulic acid is evaluated. In particular, this report contains the first systematic study of the addition of (hetero)aryllithium reagents to 3‐phenylpropenoyl Weinreb amides. The relevance of this “bioinspired” method is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, curcuminoids, and (heteroaryl) chalcones.

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Synthesis and evaluation of biological properties of benzylideneacetophenone derivatives

Cited by 19 publications

References 15 publications

The Neuroprotective Effects of Benzylideneacetophenone Derivatives on Excitotoxicity and Inflammation via Phosphorylated Janus Tyrosine Kinase 2/Phosphorylated Signal Transducer and Activator of Transcription 3 and Mitogen-Activated Protein K Pathways

The Neuroprotective Effects of Benzylideneacetophenone Derivatives on Excitotoxicity and Inflammation via Phosphorylated Janus Tyrosine Kinase 2/Phosphorylated Signal Transducer and Activator of Transcription 3 and Mitogen-Activated Protein K Pathways

Neuroprotective effect of benzylideneacetophenone derivative on the MPTP model of neurodegeneration in mice

Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: A Reactivity Study towards O‐, N‐, S‐, and C‐Nucleophiles

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