Synthesis, Structure, and Anti-Inflammatory Activity of Functionally Substituted Chalcones and Their Derivatives

Нуркенов, О. А.; Ibraev, M. K.; Schepetkin, Igor A.; Khlebnikov, Аndrei I.; Сейлханов, Т. М.; Аринова, А. Е.; Isabaeva, M. B.

doi:10.1134/s1070363219070028

Cited by 18 publications

(8 citation statements)

References 14 publications

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“…Chalcones are not only important intermediates in the biosynthesis of flavonoids, but are also valuable starting materials for the synthesis of biologically important heterocycles such as pyrazolines, isoxazolines, benzodiazepines and benzothiazepines (Zhuang et al, 2017;Ovonramwen et al, 2019). Chalcones and their derivatives have been reported to possess a number of interesting biological properties such as anti-inflammatory (Nurkenov et al, 2019;Vá squez-Martínez et al, 2019;Hsieh et al, 2000), anticancer (Dimmock et al, 1998;Bonakdar et al, 2017;Lim et al, 2020;Shaik et al, 2020), antioxidant (Ohkatsu & Satoh et al, 2008;Venkatachalam et al, 2012;Vá squez-Martínez et al, 2019;Shaik et al, 2020), antimicrobial (Fang et al, 2014;Vá squez-Martínez et al, 2019;Shaik et al, 2020) and anti-diabetic activities (Hsieh et al, 2012;Rammohan et al, 2020;Konidala et al, 2020). Besides that, compounds with a phenoxy-N-arylacetamide scaffold have demonstrated a variety of biological activities such as antimicrobial (Berest et al, 2011;Patel et al, 2013;Williams et al, 2015), antiviral (Paramonova et al, 2017), anti-diabetic (Li et al, 2015), anti-inflammatory (Rani et al, 2014), analgesic (Rani et al, 2014) and anticancer (Berest et al, 2011;Rani et al, 2014) activities.…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide

et al. 2021

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The title compound N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide, C24H21NO4, was prepared from reaction of N-(4-methoxyphenyl)-2-chloroacetamide and (E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one, which was obtained from the reaction of 4-hydroxybenzaldehyde and acetophenone. The structure of the title compound was determined by IR, 1H-NMR, 13C-NMR and HR–MS spectroscopic data and further characterized by single-crystal X-ray diffraction. The asymmetric unit contains four molecules, each displaying an E-configuration of the C=C bond. The dihedral angle between the phenyl rings in each molecule varies between 14.9 (2) and 45.8 (2)°. In the crystal, C—H...O hydrogen-bonding interactions link the molecules into chains running along the [001] direction. In addition, C—H...π interactions further stabilize the crystal packing. A Hirshfeld analysis indicates that the most important contributions to the surface contacts are from H...H (43.6%), C...H/H...C (32.1%) and O...H/H...O (18.1%) interactions.

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Section: Chemical Contextmentioning

confidence: 99%

Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide

et al. 2021

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“…This material was prepared from 2,3dihydrobenzo[b] [1,4]dioxine-6-carbaldehyde. Washing with ethanol was performed followed by recrystallization from xylene.…”

Section: (E)-1-([11'-biphenyl]-4-yl)-3-(23dihydrobenzo[b][14]dioxin-6-yl)prop-2-en-1-one (Ch6)mentioning

confidence: 99%

“…They are easy to prepare costeffectively and could be developed as drug candidates for different diseases. Chalcones showed a broad spectrum of biological properties including antiinflammatory, anticancer, antibacterial, antifungal, and antiviral [1][2][3][4][5][6]. They are also intermediates and precursors for different cyclic compounds such as isoxazole, pyrimidines, pyrazolines, etc.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Identification and Study of the Anti-microbial Activity of Novel Chalcone and Epoxy Chalcone Compounds

2021

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In this study, new chalcone and epoxy chalcone synthesized by condensation of 4-acetylbiphenyl with the appropriate aldehydes. The epoxy chalcone prepared via the reaction chalcone with alkaline hydrogen peroxide in methanol. We characterized their mass spectra and 1 H, 13 C-NMR, and 2D-HSQC spectra to confirm their structure and absolute configuration. The target compounds were then screened for their potential antibacterial and antifungal activities. Most of the tested chalcone compounds had better activity against the fungal strains Fusarium and Aspergillus niger.

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“…Nurkenov et al studied the in vitro anti-inflammatory effect of chalcones (57) to inhibit the lipopolysaccharide-induced production of anti-inflammatory cytokine interleukin-6 and tumor necrosis factor [59].…”

Section: Anti-inflammatory Chalconesmentioning

confidence: 99%

Biological Role of Chalcones in Medicinal Chemistry

Tekale¹,

Mashele²,

Pooe³

et al. 2020

Vector-Borne Diseases - Recent Developments in Epidemiology and Control

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Chalcones are promising synthons and bioactive scaffolds of great medicinal interest due to their numerous pharmacological and biological activities. They are well recognized to possess antimicrobial, anticancer, antitubercular, antioxidant, anti-inflammatory, antileishmanial, and other significant biological activities. This chapter highlights recent updates and applications of chalcones as biologically, pharmacologically, and medicinally important entities.

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Synthesis, Structure, and Anti-Inflammatory Activity of Functionally Substituted Chalcones and Their Derivatives

Cited by 18 publications

References 14 publications

Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide

Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide

Synthesis, Identification and Study of the Anti-microbial Activity of Novel Chalcone and Epoxy Chalcone Compounds

Biological Role of Chalcones in Medicinal Chemistry

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