Synthesis and Antibacterial Activity of Some Heterocyclic Chalcone Analogues Alone and in Combination with Antibiotics

Tran, Thanh-Dao; Nguyen, Thi-Thao-Nhu; Do, Tuong-Ha; Huynh, Thi-Ngoc-Phuong; Tran, Cat-Dong; Thai, Khac-Minh

doi:10.3390/molecules17066684

Cited by 102 publications

(53 citation statements)

References 32 publications

(31 reference statements)

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“…In addition to the alterations on the substitution pattern of the aromatic rings, some heterocyclic chalcone analogues were synthesized to evaluate their antibacterial activity against MSSA and MRSA. According to the results, it is indicated that replacement of aromatic ring B by heterocyclic ring containing nitrogen, oxygen, or sulfur atoms dose not significantly enhance the antibacterial activity [82]. More over, some bischalcone derivatives have also been synthesized and investigated on their activity against E. coli, P. aeruginosa, and C. albicans.…”

Section: Chalconementioning

confidence: 97%

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Fei¹,

Yang²,

Tang³

et al. 2014

CMC

586

369

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Flavonoids are well known as antibacterial agents against a wide range of pathogenic microorganism. With increasing prevalence of untreatable infections induced by antibiotic resistance bacteria, flavonoids have attracted much interest because of the potential to be substitutes for antibiotics. In this review, the structure-relationship of flavonoids as antibacterial agents is summarized, and the recent advancements on the antibacterial mechanisms of flavonoids are also discussed. It is concluded that hydroxyls at special sites on the aromatic rings of flavonoids improve the activity. However, the methylation of the active hydroxyl groups generally decreases the activity. Besides, the lipopholicity of the ring A is vital for the activity of chalcones. The hydrophobic substituents such as prenyl groups, alkylamino chains, alkyl chains, and nitrogen or oxygen containing heterocyclic moieties usually enhance the activity for all the flavonoids. The proposed antibacterial mechanisms of flavonoids are as follows: inhibition of nucleic acid synthesis, inhibition of cytoplasmic membrane function, inhibition of energy metabolism, inhibition of the attachment and biofilm formation, inhibition of the porin on the cell membrane, alteration of the membrane permeability, and attenuation of the pathogenicity.

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Section: Chalconementioning

confidence: 97%

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Fei¹,

Yang²,

Tang³

et al. 2014

CMC

586

369

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“…Due to these activities, this class of compounds has a wide application in pharmaceutical industry. [5][6][7][8][9][10] Additionally to chalcones, several studies have been reported about the heterocyclic chalcones due to their pharmacological activities, which are attributed to the structural aspects of these molecules, especially (i) the unsaturated bond between the aliphatic carbons; (ii) the ketone group; and (iii) the presence of heteroatoms. 6,11,12 The heterocyclic chalcones have a heteroaryl which contain an oxygen, sulfur or nitrogen.…”

Section: Introductionmentioning

confidence: 99%

“…Nonlinear optical materials have attracted considerable attention due to their potential applications, including signal processing for integrated optical applications and other sections of material sciences, such as ultra-fast optical communications, e.g., the ultra-fast response time feature enabling applications of organic crystals in photonic devices. 1,2,5 The heterocyclic chalcone (2E)-3-(4-methylphenyl)-1-(pyridin-3-yl)-prop-2-en-1-one (MPH) was synthesized by heterogeneous base catalysis, and crystallized by slow evaporation from ethanol. 25 The present work aims to compare structurally two independent molecules observed in the asymmetric unit and analyze the supramolecular arrangement, intermolecular interactions and contacts, and also Hirshfeld surfaces of both conformers.…”

Section: Introductionmentioning

confidence: 99%

Hirshfeld Surfaces and Nonlinear Optics on Two Conformers of a Heterocyclic Chalcone

Custódio¹,

Moreira²,

Valverde³

et al. 2017

J. Braz. Chem. Soc.

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Heterocyclic chalcones have been prominent in the scientific community due to various biological activities reported for these compounds. The structural knowledge of heterocyclic chalcones can help in the understanding of their mechanism of action. The Hirshfeld surfaces were used to study the supramolecular arrangement of two conformers present into asymmetric unit of the heterocyclic chalcone (2E)-3-(4-methylphenyl)-1-(pyridin-3-yl)-prop-2-en-1-one on crystalline state. In addition, the linear polarizability (α), the first hyperpolarizability (β||z), and the second hyperpolarizability (γ) of the conformers were calculated to get a better insight on the linear and nonlinear optical behaviors of these structures in presence of solvent medium, as well as their band-gap energies. The Hirshfeld surfaces confirmed the presence of C−H···N, C−H···O and C−H···C interactions in packaging stabilization. Finally, the 2D fingeprint plot was used to the quantification of contacts and indicated that there are both π···π and C−H···π interactions present in the compound.

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“…Ten benzylaminochalcones derivatives (A1-A10) with different substituents on ring B were prepared as shown in Scheme 1 [21][22][23][24][25]. The 1-(4-((2-Hydroxybenzyl)amino)phenyl)-ethanone 1 and benzaldehyde derivatives (in proportion of 1:1) were dissolved in methanol with stirring.…”

Section: General Procedures For the Preparation Of Compounds A1-a10mentioning

confidence: 99%

Synthesis of Novel Chalcones as Acetylcholinesterase Inhibitors

Tran

Nguyen

et al. 2016

Applied Sciences

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Abstract:A new series of benzylaminochalcone derivatives with different substituents on ring B were synthesized and evaluated as inhibitors of acetylcholinesterase. The study is aimed at identification of novel benzylaminochalcones capable of blocking acetylcholinesterase activity for further development of an approach to Alzheimer's disease treatment. These compounds were produced in moderate to good yields via Claisen-Schmidt condensation and subjected to an in vitro acetylcholinesterase inhibition assay, using Ellman's method. The in silico docking procedure was also employed to identify molecular interactions between the chalcone compounds and the enzyme. Compounds with ring B bearing pyridin-4-yl, 4-nitrophenyl, 4-chlorophenyl and 3,4-dimethoxyphenyl moieties were discovered to exhibit significant inhibitory activities against acetylcholinesterase, with IC 50 values ranging from 23 to 39 µM. The molecular modeling studies are consistent with the hypothesis that benzylaminochalcones could exert their effects as dual-binding-site acetylcholinesterase inhibitors, which might simultaneously enhance cholinergic neurotransmission and inhibit β-amyloid aggregation through binding to both catalytic and peripheral sites of the enzyme. These derivatives could be further developed to provide novel leads for the discovery of new anti-Alzheimer drugs in the future.

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Synthesis and Antibacterial Activity of Some Heterocyclic Chalcone Analogues Alone and in Combination with Antibiotics

Cited by 102 publications

References 32 publications

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Antibacterial Activities of Flavonoids: Structure-Activity Relationship and Mechanism

Hirshfeld Surfaces and Nonlinear Optics on Two Conformers of a Heterocyclic Chalcone

Synthesis of Novel Chalcones as Acetylcholinesterase Inhibitors

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