Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones

Liu, Gai-Zhi; Xu, Haiwei; Wang, Peng; Lin, Zongtao; Duan, Ying-Chao; Zheng, Jiaxin; Liu, Hong‐Min

doi:10.1016/j.ejmech.2013.04.062

Cited by 20 publications

(10 citation statements)

References 27 publications

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“…In this paper, the solubility data were also correlated with the Buchowski–Ksiazaczak λh model. where λ and h are the model parameters and were listed in Table , x is the mole fraction solubility, T and T m are the experimental temperature and normal melting temperature. The melting temperature ( T m ) is 398.15 K, which is reported by GaiZhi Liu et al, and we also measured the melting temperature by digital melting point tester (type: WRS-1B) three times, and the melting temperatures were 398.45K, 397.95K and 398.25K. The melting temperature is closed to the reported one.…”

Section: Resultssupporting

confidence: 50%

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Solubility of 4-Methylsulfonylacetophenone in Nine Pure Solvents and (Ethyl Acetate + n-Hexane) Binary Solvent Mixtures from 278.15 K to 328.15 K

Hao

Yang

et al. 2016

J. Chem. Eng. Data

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We focus on the solubility of 4-methylsulfonylacetophenone. A gravimetric method was taken to measure the solubility of 4-methylsulfonylacetophenone in n-hexane, ethyl acetate, methanol, ethanol, n-propyl alcohol, n-butyl alcohol, ethylene glycol, cyclohexane, isobutyl alcohol, and (ethyl acetate + n-hexane) binary solvent mixtures from 278.15 K to 328.15 K under atmospheric pressure. Its corresponding (solid + liquid) equilibrium results will provide essential support for further theoretical studies. The solubility of 4-methylsulfonylacetophenone in nine pure solvents were correlated with λh and Apelblat models, while 4-methylsulfonylacetophenone in (ethyl acetate + n-hexane) binary solvent mixtures were correlated with the Apelblat and CNIBS/R–K models. The Apelblat model was proven to be the best-fit model for correlating the solubility of both pure solvents and binary solvents mixtures from the analysis of the STATISTIC.

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Section: Resultssupporting

confidence: 50%

“…where λ and h are the model parameters and were listed in by GaiZhi Liu et al 13 , and we also measured the melting temperature by digital melting point tester (type: WRS-1B) three times, and the melting temperatures were 398.45K, 397.95K and 398.25K. The melting temperature is closed to the reported one.…”

Section: Resultsmentioning

confidence: 90%

Solubility of 4-Methylsulfonylacetophenone in Nine Pure Solvents and (Ethyl Acetate + n-Hexane) Binary Solvent Mixtures from 278.15 K to 328.15 K

Hao

Yang

et al. 2016

J. Chem. Eng. Data

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show abstract

“…The mixture was then cooled and the precipitate was filtered off and washed with methanol on a filter and 2a1 was obtained as light-yellow crystals, which produced the desired compounds in good yield (up to 91%). [33,34]. All compounds obtained are soluble in THF and dichloromethane.…”

Section: Methodsmentioning

confidence: 99%

“…The selectivity of the aldol condensation was sufficiently high to generate Z-isomers that were confirmed by X-ray crystal analysis (CCDC deposit number: 2063013, Figure S1). [33] TDDFT (Time-Dependent Density Functional Theory) Calculations TDDFT calculations at the B3LYP/6-311++G(2d, p) level in DMSO were performed to predict the absorption and emission spectra for compounds 2a2, 2a6, 2a12 and 2a16 using Gaussian 09 package. Solvent effects were taken into account by employing the default IEFPCM model for DMSO.…”

Section: Methodsmentioning

confidence: 99%

Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their Solvatochromism, AIE Activity, Mechanochromism, and COX-2-Targeted Bioimaging

Xie

Zheng

et al. 2021

Anal. Chem.

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Cyclooxygenase-2 (COX-2) fluorescent probes are promising tools for early cancer diagnosis. Traditionally, COX-2 probes were designed by connecting two parts, a fluorophore and a COX-2 binding unit, via a flexible linker. Herein, a new class of COX-2-specific fluorescent probes have been developed by one-step modification from rofecoxib by an integrative approach to combining the fluorophore and binding units into one. Among them, several new rofecoxib analogues not only retained their COX-2 binding ability but also exhibited attractive fluorescent properties, such as tunable Blue-Red emission, solvatochromism, AIE behavior and mechanochromism. Notably, the emission of 2a16 can be switched between greenish-yellow in the crystalline state to red-orange in the amorphous state by grinding and fuming treatments. Furthermore, the highly fluorescent compound 2a16 (Фf = 0.94 in powder) displayed much stronger fluorescent imaging of COX-2 in HeLa cancer cells overexpressing COX-2 than RAW264.7 normal cells with minimal expressing of COX-2. Most importantly, 2a16 can light up human cancer tissues from adjacent normal tissues with much brighter fluorescence by targeting COX-2 enzyme. These results illustrate the potential of 2a16 as a new red fluorescent probe for human cancer imaging in clinical applications.

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“…The selectivity of the aldol condensation was sufficiently high to generate Z-isomers that were confirmed by X-ray crystal analysis (CCDC deposit number: 2063013, Figure S1). [33]…”

Section: Methodsmentioning

confidence: 99%

Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their AIE Activity, Solvatochromism, Mechanochromism and COX-2 Targeted Bioimaging

Xie

Zheng

et al. 2021

Preprint

View full text Add to dashboard Cite

Cyclooxygenase-2 (COX-2) fluorescent probes are promising tools for early cancer diagnosis. Traditionally, COX-2 probes were designed by connecting two parts, a fluorophore and a COX-2 binding unit, via a flexible linker. Herein, a new class of COX-2-specific fluorescent probes have been developed by one-step modification from rofecoxib by an integrative approach to combining the fluorophore and binding units into one. Among them, several new rofecoxib analogues not only retained their COX-2 binding ability but also exhibited attractive fluorescent properties, such as tunable Blue-Red emission, solvatochromism, AIE behavior and mechanochromism.Notably, the emission of 2a16 can be switched between greenish-yellow in the crystalline state to red-orange in the amorphous state by grinding and fuming treatments. Furthermore, the highly fluorescent compound 2a16 (Фf = 0.94 in powder) displayed much stronger fluorescent imaging of COX-2 in HeLa cancer cells overexpressing COX-2 than RAW264.7 normal cells with minimal expressing of COX-2. Most importantly, 2a16 can light up human cancer tissues from adjacent normal tissues with much brighter fluorescence by targeting COX-2 enzyme. These results illustrate the potential of 2a16 as a new red fluorescent probe for human cancer imaging in clinical applications.

show abstract

Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones

Cited by 20 publications

References 27 publications

Solubility of 4-Methylsulfonylacetophenone in Nine Pure Solvents and (Ethyl Acetate + n-Hexane) Binary Solvent Mixtures from 278.15 K to 328.15 K

Solubility of 4-Methylsulfonylacetophenone in Nine Pure Solvents and (Ethyl Acetate + n-Hexane) Binary Solvent Mixtures from 278.15 K to 328.15 K

Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their Solvatochromism, AIE Activity, Mechanochromism, and COX-2-Targeted Bioimaging

Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their AIE Activity, Solvatochromism, Mechanochromism and COX-2 Targeted Bioimaging

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