Design, synthesis, and structure&amp;ndash;activity relationships of 2-benzylidene-1-indanone derivatives as anti-inflammatory agents for treatment of acute lung injury

Xiao, Siyang; Zhang, Wenxin; Chen, Hongjin; Fang, Bo; Qiu, Yinda; Chen, Xianxin; Chen, Lingfeng; Shu, Shengqiang; Zhang, Yali; Zhao, Yunjie; Liu, Zhiguo; Liang, Guang

doi:10.2147/dddt.s160314

Cited by 19 publications

(9 citation statements)

References 32 publications

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“…The simple chemical structure ( Figure 1 ) and a wide range of modifications in their molecules increase the ability of chalcones to affect various molecular and cell signaling targets in the organism [ 8 ]. Plenty of studies have documented numerous biological actions of chalcones including anti-inflammatory [ 16 ], antirheumatic [ 17 ], antidiabetic [ 18 ], antimicrobial [ 19 , 20 , 21 ], immunomodulatory [ 22 ], antimalarial [ 23 ], antiparasitic [ 24 ], and antiproliferative [ 25 , 26 ] effects. Moreover, the anticancer effect of chalcones in experimental animals has also been shown [ 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

Molecular Mechanisms of Antiproliferative Effects of Natural Chalcones

Michalková¹,

Mirossay²,

Gazdova³

et al. 2021

Cancers

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Although great progress has been made in the treatment of cancer, the search for new promising molecules with antitumor activity is still one of the greatest challenges in the fight against cancer due to the increasing number of new cases each year. Chalcones (1,3-diphenyl-2-propen-1-one), the precursors of flavonoid synthesis in higher plants, possess a wide spectrum of biological activities including antimicrobial, anti-inflammatory, antioxidant, and anticancer. A plethora of molecular mechanisms of action have been documented, including induction of apoptosis, autophagy, or other types of cell death, cell cycle changes, and modulation of several signaling pathways associated with cell survival or death. In addition, blockade of several steps of angiogenesis and proteasome inhibition has also been documented. This review summarizes the basic molecular mechanisms related to the antiproliferative effects of chalcones, focusing on research articles from the years January 2015–February 2021.

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Section: Introductionmentioning

confidence: 99%

Molecular Mechanisms of Antiproliferative Effects of Natural Chalcones

Michalková¹,

Mirossay²,

Gazdova³

et al. 2021

Cancers

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“…We synthesized Ziziphus spina-christi (Jujube) root-loaded silver oxide nanoparticles (ZS-Ag-NPs) with a minimal nanometer size and uniform dispersion, which was confirmed by Zetasizer, TEM, FT-IR, and XRD pattern analyses. Such successful synthesis of silver oxide nanoparticles, with potential biological activities, has been mentioned earlier [33,38,48]. As mentioned above, Ziziphus spina-christi (Jujube) root extract contained some phenolic compounds, such as Kaempferol.…”

Section: Discussionmentioning

confidence: 83%

“…For instance, it is a precursor moiety of donepezil (IV), an acetylcholinesterase inhibitor that has been approved by the US Food and Drug Administration for the treatment of Alzheimer's disease [32]. Some 2-benzylidene-1-indanone derivatives have anti-inflammatory effects against acute lung injury [33]. Synthesized 1,4-Phthalazinedione derivatives are found to display a vasorelaxant activity [34] and antibacterial activity [35].…”

Section: Discussionmentioning

confidence: 99%

Synthesis of Ziziphus spina-christi (Jujube) Root Methanol Extract Loaded Functionalized Silver Nanoparticle (ZS-Ag-NPs); Physiochemical Characterization and Effect of ZS-Ag-NPs on Adipocyte Maturation, Adipokine and Vascular Smooth Muscle Cell Interaction

et al. 2021

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In this research, a simple, green approach was employed to synthesize silver nanoparticles with the aid of Ziziphus spina-christi (L.) methanol root extract, which can act as a reducing, capping agent to treat obesity and inflammation. Globally, Ziziphus spina-christi (Jujube) root is used in traditional therapy as a lipolysis promoter. GC-MS results confirmed the availability of kaempferol (flavonol), cannabinol and indole-3-carboxylic acid in Ziziphus spina-christi root methanol extract (ZSE). ZSE silver nanoparticles (ZS-Ag-NPs) were synthesized and their effect on mitochondrial fatty acid oxidation capacity and adipokine levels in maturing adipocytes were analyzed. Maturing adipocytes treated with 0.4 µg/dL of ZSE and ZS-Ag-NPs significantly reduced the lipid content in adipocytes by 64% and 82%, respectively. In addition, lipolysis-related genes such as LPL (1.9 fold), HSL (2.3 fold), PGC-1α (3 fold), UCP-1 (4.1 fold), PRDM16 (2 fold) and PPARα (2.7 fold) increased significantly in ZS-Ag-NPs treated maturing adipocytes. The ZS-Ag-NPs treatment significantly decreased insulin resistance and metabolic inflammation-related LTB4-R, TNF-α, IL-4 and STAT-6 mRNA levels. Mitochondrial thermogenesis stimulating capacity of ZS-Ag-NPs was further confirmed by the significantly enhanced CREB-1 and AMPK protein levels in adipocytes. Furthermore, ZS-Ag-NPs treated adipokines (condition media, CM) were treated with human umbilical vein endothelial cells (HUVECs) to determine cytotoxicity and pro-inflammatory stimulus capacity. We found that ZS-Ag-NPs treated adipocyte CM effectively increased mRNA expression levels of the vascular endothelial cell growth factor (VEGF), and down-regulated oxidative stress (LPO, eNOS, and HO) and vascular cell inflammation (ICAM, VCAM, TNF-α, IL-1β, and NF-κB). In conclusion, ZS-Ag-NPs displayed an action at the molecular level in mitochondrial fatty acid oxidation, decreased adipokine secretion in adipocytes, and enhanced vascular endothelial cell growth. This molecular mechanical action of ZS-Ag-NPs reduced effectively obesity progressions and metabolic inflammatory pathogenesis associated with aging.

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“…[36][37][38][39][40][41] Moreover, they are likewise researched as antagonists for neurological treatment, antiinflammatory, antitubercular, breast cancer therapeutics, antioxidant, and antimicrobial agents. [42][43][44][45][46][47] In continuation of our previous work and by considering these vital aspects, a successful attempt investigates structural parameters such as total energy, electron density in highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), charge density, absolute electronegativity (χ), softness (σ), hardness (ɳ), and electron transferred (ΔN) of previously synthesized arylidene indanones. Importantly, single-crystal examination study for (E)-7-(2-chlorobenzylidene)-1,2,6,7-tetrahydro-8H-inde no [5,4-b]furan-8-one (CBIF) has also been presented.…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical exploration on single crystal, structural, and quantum chemical parameters of (E)‐7‐(arylidene)‐1,2,6,7‐tetrahydro‐8H‐indeno[5,4‐b]furan‐8‐one derivatives: A comparative study

Adole¹,

Jagdale²,

Pawar³

et al. 2020

J Chinese Chemical Soc

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In the present research work, biologically important halogen-substituted (E)-7-(arylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one derivatives are studied from a structural investigation point of view. For a detailed molecular structure description, some quantum-chemical calculations were performed by using the density functional theory method with a basis set 6-311++G(d,p). The optimized molecular geometry, bond length, atomic charges, bond angle, and harmonic vibrational frequencies have been investigated. The quantum and structural entities such as total energy, electron density distribution in highest occupied molecular orbital and lowest unoccupied molecular orbital, charge distribution, electronegativity, absolute hardness (η), softness, electrophilicity, chemical potential, and charge transfer in molecules (ΔN max) have been computed using 6-311++G(d,p) basis set. Importantly, single-crystal analysis study for (E)-7-(2-chlorobenzylidene)-1,2,6,7-tetrahydro-8H-indeno[5,4-b] furan-8-one (CBIF) has been presented. The single-crystal examination reveals CBIF has triclinic crystal lattice with nonclassical intermolecular short contact interactions. The vibrational wavenumbers are calculated and the scaled values are compared with the experimental FT-IR spectrum. Furthermore, the molecular electrostatic potential (MEP) and some thermodynamic functions were also explored using computational work. The theoretical geometrical parameters have been compared with the experimental results obtained from the single-crystal examination.

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Design, synthesis, and structure–activity relationships of 2-benzylidene-1-indanone derivatives as anti-inflammatory agents for treatment of acute lung injury

Cited by 19 publications

References 32 publications

Molecular Mechanisms of Antiproliferative Effects of Natural Chalcones

Molecular Mechanisms of Antiproliferative Effects of Natural Chalcones

Synthesis of Ziziphus spina-christi (Jujube) Root Methanol Extract Loaded Functionalized Silver Nanoparticle (ZS-Ag-NPs); Physiochemical Characterization and Effect of ZS-Ag-NPs on Adipocyte Maturation, Adipokine and Vascular Smooth Muscle Cell Interaction

Experimental and theoretical exploration on single crystal, structural, and quantum chemical parameters of (E)‐7‐(arylidene)‐1,2,6,7‐tetrahydro‐8H‐indeno[5,4‐b]furan‐8‐one derivatives: A comparative study

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