Recent developments of chalcones as potential antibacterial agents in medicinal chemistry

Dan, Wenjia; Dai, Jiangkun

doi:10.1016/j.ejmech.2019.111980

Cited by 147 publications

(79 citation statements)

References 85 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…They serve as biogenic key precursors of flavonoids in higher plants. [1][2][3] The presence of two electrophilic reaction centres enables them to participate in the synthesis of heterocyclic compound. 4 They demonstrate wide range of biological activities such as antiviral, 5 anti-inflammatory, anticancer, antimicrobial, 6 antioxidant, 7 and anti-malerial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, antimicrobial screening and cytotoxic properties of Cu(II) and Zn(II) complexes with bidentate hydroxylated 1,3-diaryl-2-propene-1-ones ligand

Patil¹,

Zangade

2021

JSCS

View full text Add to dashboard Cite

A series of binary metal complexes [halo, hydroxyl and methoxy sub-stituted bis (2-(E) acryloyl)naphthalen-1-yl)oxy)Cu(II) and Zn(II) (C1-C10)] of Cu2+ and Zn2+ ions derived from bi-coordinated hydroxylated 1,3-diaryl-2- -propene-1-ones were synthesized. The newly synthesized metal complexes were structurally determined by FT-IR, 1H NMR, 13CNMR, ESR spectral, XRD and TGA analysis. The FT-IR and ESR studies demonstrated that interactions between metal ions with ligands occur through carbonyl oxygen and deprotonated hydroxyl oxygen and corresponds to square-planar geometry for all complexes. In-vitro the metal complexes were screened and evaluated for their antimicrobial and cytotoxic activity. The complexes C1 and C4 showed the significant antimicrobial activity while the remaining complexes were showed the moderately antimicrobial activity against the tested pathogens. The complexes were evaluated for cytotoxic activity against the organism Artemia salina. The complexes C2, C3, C4 and C5 were showed the LC50 values as 630.45, 969.99, 921.94 and 918.41 ?M mL-1 respectively. Further complexes were evaluated for anticancer activity against liver cancer cell line (Hep G2) in comparison with 5-fluorouracil standard. The complex C5 showed the significant IC50 value 58.94 ?g mL-1. Therefore the present study is useful to develop the new class of antimicrobial and anticancer agents.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, antimicrobial screening and cytotoxic properties of Cu(II) and Zn(II) complexes with bidentate hydroxylated 1,3-diaryl-2-propene-1-ones ligand

Patil¹,

Zangade

2021

JSCS

View full text Add to dashboard Cite

show abstract

“…The great interest in chalcones is influenced by the ease of synthesis of these compounds and the extensive biological activity characteristics they exhibit: in particular antiviral, anthelmintic, antibacterial, antiprotozoal, insecticidal, antiulcer, cytotoxic, and anticancer [ 11 , 12 , 13 ]. Due to the confirmed therapeutic effect of chalcones on human cancer, we decided to check their activity against canine cancer cells.…”

Section: Introductionmentioning

confidence: 99%

Chalcone Methoxy Derivatives Exhibit Antiproliferative and Proapoptotic Activity on Canine Lymphoma and Leukemia Cells

et al. 2020

View full text Add to dashboard Cite

Chalcones are interesting candidates for anti-cancer drugs due to the ease of their synthesis and their extensive biological activity. The study presents antitumor activity of newly synthesized chalcone analogues with a methoxy group on a panel of canine lymphoma and leukemia cell lines. The antiproliferative effect of the 2′-hydroxychalcone and its methoxylated derivatives was evaluated in MTT assay after 48 h of treatment in different concentrations. The proapoptotic activity was studied by cytometric analysis of cells stained with Annexin V/FITC and propidium iodide and by measure caspases 3/7 and 8 activation. The DNA damage was evaluated by Western blot analysis of phosphorylated histone H2AX. The new compounds had selective antiproliferative activity against the studied cell lines, the most effective were the 2′-hydroxy-2″,5″-dimethoxychalcone and 2′-hydroxy-4′,6′-dimethoxychalcone. 2′-Hydroxychalcone and the two most active derivatives induced apoptosis and caspases participation, but some percentage of necrotic cells was also observed. Comparing phosphatidylserine externalization after treatment with the different compounds it was noted that the addition of two methoxy groups increased the proapoptotic potential. The most active compounds triggered DNA damage even in the cell lines resistant to chalcone-induced apoptosis. The results confirmed that the analogues could have anticancer potential in the treatment of canine lymphoma or leukemia.

show abstract

“…[2] Natural product derived molecule namely chalcone has been reported to have various biological activity i. e. antiviral, antiinflammatory, antitumor, antimicrobial, antifungal, antihyperglycemic, antidiabetic, anti HIV and antituberculosis. [3] Based on the literature precedent, the α, β-unsaturated ketone has been reported as a responsible moiety for antimicrobial activities in chalcone [4] besides other factors such as the effect of bacterial strain, nature of bacteria, size of molecule, lipophilicity and number or position of substituents. [5] The replacement of substituents in the molecules such as hydroxyl group to carboxyl moiety at either ring A and B can also increase the solubility and biological properties of chalcones.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Docking and Antimicrobial Activity of α, β‐Unsaturated Ketone Exchange Moiety for Chalcone and Pyrazoline Derivatives

Farooq

Ngaini

2020

ChemistrySelect

View full text Add to dashboard Cite

Bacterial diseases cause hazardous infections due to the occurrence of bacterial resistance. Drugs production to cure bacterial resistance from natural sources has become ineffective to execute the resisted bacteria due to the unsuitable binding interaction of active sites with the receptors. Drug link to natural products moieties such as chalcones and pyrazolines, which originated from plants extracts, has become attractive among researchers due to its significant pharmaceutical moiety. In this study a series of chalcone derivatives (1 a–d) has been synthesized via Claisen‐Schmidt condensation, followed by cyclization to form pyrazolines (2 a–d, 3 a–d). Fischer esterification of pyrazolines formed 4 a–d in moderate to good yield (42.91‐88.23 %). Antimicrobial activities of all the synthesized compounds were evaluated against Escherichia coli and Staphylococcus aureus via disc diffusion. Among all compounds, pyrazolines 3 c and 3 d showed the highest zone of inhibition (17 mm) compared to 1 a‐d (5‐11 mm) and standard ampicillin (11 mm). The exchange of α, β‐unsaturated carbonyl showed phenomenal increment in the biological activities. Structure activity relationship of 1 a, 1 d, 3 a and 3 d was analyzed via molecular docking of N‐terminal domain having deoxyribonucleic acid (DNA) binding protein (4pql) with excellent binding energy of −6.2, −6.6, −7.1 and −7.2 kcal/mol, respectively. This work is significant in designing new drugs with keto‐exchange relationship for medicinal industry.

show abstract

Recent developments of chalcones as potential antibacterial agents in medicinal chemistry

Cited by 147 publications

References 85 publications

Synthesis, characterization, antimicrobial screening and cytotoxic properties of Cu(II) and Zn(II) complexes with bidentate hydroxylated 1,3-diaryl-2-propene-1-ones ligand

Synthesis, characterization, antimicrobial screening and cytotoxic properties of Cu(II) and Zn(II) complexes with bidentate hydroxylated 1,3-diaryl-2-propene-1-ones ligand

Chalcone Methoxy Derivatives Exhibit Antiproliferative and Proapoptotic Activity on Canine Lymphoma and Leukemia Cells

Synthesis, Molecular Docking and Antimicrobial Activity of α, β‐Unsaturated Ketone Exchange Moiety for Chalcone and Pyrazoline Derivatives

Contact Info

Product

Resources

About