Novel 2,6-disubstituted benzofuran-3-one analogues improve cerebral ischemia/reperfusion injury via neuroprotective and antioxidative effects

Yang, Zunhua; Luo, Gengzhuo; Ying, Yuqing; Li, Huilan; Yang, Wankou; Xu, Guoliang; Li, Mingdong; Xian, Yuezhong; Feng, Yulin; Yuan, Fang

doi:10.1016/j.bioorg.2023.106346

Cited by 7 publications

(7 citation statements)

References 31 publications

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“…The neuroprotective capabilities of target compounds were assessed using oxygen glucose deprivation/reperfusion (OGD/R) models in primary rat neuronal cells at concentrations ranging from 1.875 to 15 μM. NBP and edaravone served as positive controls, and cell viability was determined through the cell counting kit-8 (CCK-8) assay . The neuroprotective results of 13 compounds without nitrate ( 4 , 5 , 6 , 7 , 8 , 9 , 10 , 25 , 26 , 38 , 39 , 51 , and 52 ) are outlined in Figure .…”

Section: Resultsmentioning

confidence: 99%

“…MS-ESI [M + H] + : 195.2. (32). Following the similar synthetic procedure of 12, the title compound was obtained as a yellow solid with 88% yield.…”

Section: -(4-bromobutoxy)-23-dihydro-1h-inden-1-one (29)mentioning

confidence: 99%

“…NBP and edaravone served as positive controls, and cell viability was determined through the cell counting kit-8 (CCK-8) assay. 32 The neuroprotective results of 13 compounds without nitrate (4,5,6,7,8,9,10,25,26,38,39, 51, and 52) are outlined in Figure 3. Also, the results of 14 nitrate compounds are shown in Figure 4.…”

Section: Neuroprotection Of Compounds On Oxygen Glucose Deprivation/r...mentioning

confidence: 99%

“…In our investigation of the BBB permeability of potent compounds, we conducted the parallel artificial membrane permeability assay (PAMPA) to predict the BBB permeation using a procedure reported previously. 32 Compounds 4, 15,22,26,35,36,37,48,49, and 51 were selected for PAMPA assessment. Table 1 reveals that all tested compounds exhibited permeability (Pe) values surpassing the threshold (Pe = 4 × 10 6 cm/s).…”

Section: Bbb Permeation Assaysmentioning

confidence: 99%

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Synthesis and Neuroprotective Evaluation of Substituted Indanone/Benzofuranone and Piperidine Hybrids

Zeng,

Zhang,

Cai

et al. 2024

ACS Chem. Neurosci.

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Based on the neuroprotection of butylphthalide and donepezil, a series of indanone/benzofuranone and piperidine hybrids were designed and synthesized for assessment of their neuroprotective activities, aiming to enhance the bioavailability and therapeutic efficacy of natural phthalide analogues. Within this study, it was observed that most indanone derivatives bearing 1methylpiperidine in the tail segment demonstrated superior neuroprotective effects on the oxygen glucose deprivation/reperfusion (OGD/R)-induced rat primary neuronal cell injury model in vitro compared to benzofuranone compounds. Among the synthesized compounds, 11 (4, 14, 15, 22, 26, 35, 36, 37, 48, 49, and 52) displayed robust cell viabilities in the OGD/R model, along with favorable blood−brain barrier permeability as confirmed by the parallel artificial membrane permeability assay. Notably, compound 4 showed significant neuronal cell viabilities within the concentration range of 3.125 to 100 μM, without inducing cytotoxicity. Further results from in vivo middle cerebral artery occlusion/R experiments revealed that 4 effectively ameliorated ischemiareperfusion injury, reducing the infarct volume to 18.45% at a dose of 40 mg/kg. This outcome suggested a superior neuroprotective effect compared to edaravone at 20 mg/kg, further highlighting the potential therapeutic efficacy of compound 4 in addressing neurological disorders.

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Section: Resultsmentioning

confidence: 99%

“…MS-ESI [M + H] + : 195.2. (32). Following the similar synthetic procedure of 12, the title compound was obtained as a yellow solid with 88% yield.…”

Section: -(4-bromobutoxy)-23-dihydro-1h-inden-1-one (29)mentioning

confidence: 99%

Section: Neuroprotection Of Compounds On Oxygen Glucose Deprivation/r...mentioning

confidence: 99%

Section: Bbb Permeation Assaysmentioning

confidence: 99%

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Synthesis and Neuroprotective Evaluation of Substituted Indanone/Benzofuranone and Piperidine Hybrids

Zeng,

Zhang,

Cai

et al. 2024

ACS Chem. Neurosci.

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“…The neuroprotective activities of all isolated compounds toward primary rat neuronal cells in an oxygen glucose deprivation (OGD) model were examined following the reported procedures. 49…”

Section: Neuroprotection Assaysmentioning

confidence: 99%

Rapid screening of unprecedented sesquiterpenes with distinctive ring skeletons from Daphne aurantiaca employing an integrated strategy

Dong¹,

Han²,

Chang³

et al. 2023

Org. Chem. Front.

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Novel 1,3,4-oxadiazole hybrids of 3-n-butylphthalide derivatives as potential anti-ischemic stroke agents

Yu,

Li,

Luo

et al. 2024

Bioorganic Chemistry

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Novel 2,6-disubstituted benzofuran-3-one analogues improve cerebral ischemia/reperfusion injury via neuroprotective and antioxidative effects

Cited by 7 publications

References 31 publications

Synthesis and Neuroprotective Evaluation of Substituted Indanone/Benzofuranone and Piperidine Hybrids

Synthesis and Neuroprotective Evaluation of Substituted Indanone/Benzofuranone and Piperidine Hybrids

Rapid screening of unprecedented sesquiterpenes with distinctive ring skeletons from Daphne aurantiaca employing an integrated strategy

Novel 1,3,4-oxadiazole hybrids of 3-n-butylphthalide derivatives as potential anti-ischemic stroke agents

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