Synthesis and biological effects of naphthalene-chalcone derivatives

Jin, Qinghao; Chen, Hong-Hai; Chen, Wenbo; Fu, Zhiyang; Guan, Liping; Jiang, Haiying

doi:10.1007/s00044-020-02525-4

Cited by 6 publications

(5 citation statements)

References 27 publications

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“…The completion of reaction was checked by TLC analysis and the products were visualized by UV detection. (Yellow solid, yield: 60% and m.p: 84-85 o C) 1,15 . The reaction scheme of 4FNP is shown in Figure 1 Spectral Characterisation 1 H NMR spectrum of 4FNP was measured in CDCl 3 on an Agilent 400 MHz NMR spectrometer is shown in Figure 2.…”

Section: Synthesis Of 1-(4-fluorophenyl)-3-(napthalen-1yl)-2-propen-1...mentioning

confidence: 99%

“…It is found that the chalcones derived from alpha-naphthyl generally exhibit more potent anticancer activity than those of beta-naphthyl. Assessment of series of naphthalene derivatives exhibit antidepressant, anti-inflammatory and analgesic effects 1 . The studies showed that naphthalene derivatives used as a potent antimicrobial agent against different human pathogens 9 .…”

Section: Introductionmentioning

confidence: 99%

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Thermodynamic and Acoustical study of 1-(4-Fluorophenyl)-3-(napthalen-1-yl)-2-propen-1-one

Sowmya

2022

Orient. J. Chem

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The various concentrations (ranging from 0.01M to 0.1 M) of synthesized 1-(4-fluorophenyl)-3-(napthalen-1-yl)-2-propen-1-one1 (4FNP) solutions in DMF were prepared. Density (ρ), viscosity (η) and ultrasonic velocity (U) measurements of pure solvent and solutions were carried out at 288.15 K, 293.15 K, 298.15 K and 303.15 K. The observed values of ρ, η and U were found at 298.15K in the range of 944.50-954.25 kg.m-3, 0.8440 x10-3-1.4195 x10-3 Nm-2s and 1454-1513 ms-1 respectively. The values of η and U decreased with increase of temperature, reveals the weakening of intermolecular forces between the molecules at higher temparature. Calculated thermodynamic parameters such as free volume, Gibbs free energy and internal pressures were interpreted in terms solute-solvent interaction. Increase of Gibbs free energy with increase of concentration clearly indicates the strong interaction between solvent and solute molecules. Decrease of free volume with increase in mole fraction gives evidence of strong intermolecular interaction in solution. Positive excess values of internal pressure represent the presence of dispersive forces between molecules.

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Section: Synthesis Of 1-(4-fluorophenyl)-3-(napthalen-1yl)-2-propen-1...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thermodynamic and Acoustical study of 1-(4-Fluorophenyl)-3-(napthalen-1-yl)-2-propen-1-one

Sowmya

2022

Orient. J. Chem

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“…The anti-inflammatory properties of albocarbon and hybrids have been extensively studied [24][25][26][27][28][29]. Muralidharan et al [24] developed and characterized a new set of albocarbon-pyrimidine hybrids.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

“…The hybrids 8 and 13 (Figure 21) displayed a solid inhibitory impact on the production of this inflammatory mediator, with IC50 values of 2.61 and 1.32 mol/L, respectively [27]. Jin et al [28] developed, identified, and tested novel albocarbon-chalcone hybrids for anti-inflammatory efficacy. The assay was performed in mice using xylene-induced ear edema and acetic acid-induced abdominal writhing assessments.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Untitled

2022

J. Med. Chem. Sci.

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“…Chalcones, structurally, are 1,3‐diaryl‐2‐propen‐1‐ones in which a two aromatic rings (ring A and ring B, Figure 1), are joined by a three‐carbon α , β ‐unsaturated carbonyl system as depicted in Figure 1. These types of compounds that can be obtained directly by aldol reactions under basic conditions are considered as key precursors for flavonoid and isoflavonoid syntheses [1–8] …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, In silico and In Vitro Anticancer Activity of Novel Bis‐Furanyl‐Chalcone Derivatives Linked through Alkyl Spacers

et al. 2021

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A novel series of bis(furan-based chalcone) derivatives linked to aliphatic linkers, with the furan units at the A-or B-rings, were synthesized and evaluated as anticancer agents. Chalcones 5 ac in which the furan ring designed to be a B-ring were obtained from the Knoevenagel condensation reactions of the appropriate bis(acetyl) compounds 3 a-c with two equivalents of furan-2-aldehyde. Likewise, the condensation of bis(aldehydes) 7 a-c with two equivalents of 2-acetylfuran afforded the corresponding chalcones 9 a-c, in which the furan rings represent the A-rings of the chalcones, in excellent yields. The synthesized compounds have been fully characterized by 1 H-NMR, 13 C-NMR, and elemental analysis. The in vitro anticancer activity of the prepared compounds was tested against A549, HCT116, HePG2, PC3, A431 and BJ1 cell lines using MTT assay, gene expression analysis of skin and lung cancer related genes, comet assay, and DNA fragmentation assy. Compounds 9 a and 9 c were found to be the most promising, with IC 50 (24.9 and 13.7 μg/ml, respectively) against A549 compared with doxorubicin (IC 50 , 28.3 μg/ml) and IC 50 (26.1 and 14.4 μg/ml, respectively) against A431 in comparison to doxorubicin (IC 50 , 24.9 μg/ml). Comapred with neagtive control cell lines, the gene expression levels of hBD-2 and hBD-3 genes were decreased singnificantly (P < 0.05) in positive control and skin cancer cell lines (A431) treated with compounds 9 a and 9 c. The expression levels of FOSB and IL-8 genes were increased singnificantly (P < 0.05) in positive control and lung cancer cell lines (A549 and A541) treated with compounds 9 a and 9 c, respectively, comapred with neagtive control cell lines. The DNA damage was increased significantly (P < 0.001) in treated skin and lung cell lines samples compared with negative control. The negative control skin and lung cancer cell lines showed a significant decrease (P < 0.05) in DNA fragmentation rate compared with positive control. On the other hand, the DNA fragmentation rates were increased significantly (P < 0.001) in treated skin and lung cell lines samples compared with negative control. In summary, the synthesized compounds 9 a and 9 c showed a significant anticancer activity against lung and skin cancer cell lines compared with known chemotherapeutic drug (doxorubicin).

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Synthesis and biological effects of naphthalene-chalcone derivatives

Cited by 6 publications

References 27 publications

Thermodynamic and Acoustical study of 1-(4-Fluorophenyl)-3-(napthalen-1-yl)-2-propen-1-one

Thermodynamic and Acoustical study of 1-(4-Fluorophenyl)-3-(napthalen-1-yl)-2-propen-1-one

Untitled

Design, Synthesis, In silico and In Vitro Anticancer Activity of Novel Bis‐Furanyl‐Chalcone Derivatives Linked through Alkyl Spacers

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