(2<i>E</i>,4<i>E</i>)-1-(2-Hydroxyphenyl)-5-phenylpenta-2,4-dien-1-one

Silva, W. A.; Gatto, Claudia C.; Oliveira, Guilherme R.

doi:10.1107/s160053681103025x

Acta Cryst E

2011

DOI: 10.1107/s160053681103025x

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(2E,4E)-1-(2-Hydroxyphenyl)-5-phenylpenta-2,4-dien-1-one

W. A. Silva

Claudia C. Gatto

Guilherme R. Oliveira

Abstract: In the structure of the title chalcone, C17H14O2, derived from cinnamaldehyde, the olefine group has a trans configuration. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen-bond interaction with graph-set motif S(6).

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Cited by 6 publications

References 12 publications

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Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Carneiro Romão,

Costa Siqueira,

Amâncio Ferreira

et al. 2024

Chemistry & Biodiversity

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The study focuses on the anxiolytic potential of chalcone (2E,4E)‐1‐(2‐hydroxyphenyl)‐5‐phenylpenta‐2,4‐dien‐1‐one (CHALCNM) in adult zebrafish. Successfully synthesized in 58% yield, CHALCNM demonstrated no toxicity after 96 h of exposure. In behavioral tests, CHALCNM (40 mg/kg) reduced locomotor activity and promoted less anxious behavior in zebrafish, confirmed by increased permanence in the light zone of the aquarium. Flumazenil reversed its anxiolytic effect, indicating interaction with GABAA receptors. Furthermore, CHALCNM (4 and 20 mg/kg) preserved zebrafish memory in inhibitory avoidance tests. Virtual screening and ADMET profile studies suggest high oral bioavailability, access to the CNS, favored by low topological polarity (TPSA ≤ 75 Å²) and low incidence of hepatotoxicity, standing out as a promising pharmacological agent against the GABAergic system. In molecular coupling, CHALCNM demonstrated superior affinity to diazepam for the GABAA receptor. These results reinforce the therapeutic potential of CHALCNM in the treatment of anxiety, highlighting its possible future clinical application.

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Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Carneiro Romão,

Costa Siqueira,

Amâncio Ferreira

et al. 2024

Chemistry & Biodiversity

View full text Add to dashboard Cite

show abstract

Structure and theoretical approaches to a chalcone derivative

Oliveira

Silva

et al. 2012

Struct Chem

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Probing deep into the interaction of a fluorescent chalcone derivative and bovine serum albumin (BSA): an experimental and computational study

et al. 2013

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In the present manuscript, a novel fluorescent chalcone derivative is synthesized and its photophysical properties are fully characterized. The designed fluorophore is applied as a probe to study protein-dye interactions with bovine serum albumin. Circular dichroism gave interesting results on the thermodynamics of the interaction. NMR spectroscopy, especially relaxation measurements, revealed the atoms in the chalcone derivative that interacts with the protein upon binding. Molecular docking calculations indicate that the most favourable binding sites are near the two tryptophan residues. Furthermore, ab initio and DFT calculations offer insights into the reactivity and physicochemical properties of this novel fluorophore.

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(2E,4E)-1-(2-Hydroxyphenyl)-5-phenylpenta-2,4-dien-1-one

Abstract: In the structure of the title chalcone, C17H14O2, derived from cinnamaldehyde, the olefine group has a trans configuration. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen-bond interaction with graph-set motif S(6).

Cited by 6 publications

References 12 publications

Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Structure and theoretical approaches to a chalcone derivative

Probing deep into the interaction of a fluorescent chalcone derivative and bovine serum albumin (BSA): an experimental and computational study

Contact Info

Product

Resources

About

(2E,4E)-1-(2-Hydroxyphenyl)-5-phenylpenta-2,4-dien-1-one

Abstract: In the structure of the title chalcone, C17H14O2, derived from cinnamaldehyde, the olefine group has a trans configuration. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen-bond inter­action with graph-set motif S(6).

Cited by 6 publications

References 12 publications

Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Effect of Cinnamaldehyde Chalcone on Behavior in Adult Zebrafish (Danio rerio): In Silico Approach

Structure and theoretical approaches to a chalcone derivative

Probing deep into the interaction of a fluorescent chalcone derivative and bovine serum albumin (BSA): an experimental and computational study

Contact Info

Product

Resources

About

Abstract: In the structure of the title chalcone, C17H14O2, derived from cinnamaldehyde, the olefine group has a trans configuration. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen-bond interaction with graph-set motif S(6).