Synthesis, Characterization and Antibacterial Activities of New Fluorinated Chalcones

Amole, Kayode L.; Bello, Isaac Asusheyi; Oyewale, A. O.

doi:10.1007/s42250-019-00043-4

Cited by 24 publications

(13 citation statements)

References 18 publications

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“…In silico studies established DNA binding and molecular docking of these compounds. There are several other examples of synthesis antibacterial chalcones and assessment of their modes of action available in the literature [93][94][95][96][97]…”

Section: Antibacterial Activitymentioning

confidence: 99%

Chalcones: Synthetic Chemistry Follows Where Nature Leads

et al. 2021

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Chalcones belong to the flavonoid class of phenolic compounds. They form one of the largest groups of bioactive natural products. The potential anticancer, anti-inflammatory, antimicrobial, antioxidant, and antiparasitic properties of naturally occurring chalcones, and their unique chemical structural features inspired the synthesis of numerous chalcone derivatives. In fact, structural features of chalcones are easy to construct from simple aromatic compounds, and it is convenient to perform structural modifications to generate functionalized chalcone derivatives. Many of these synthetic analogs were shown to possess similar bioactivities as their natural counterparts, but often with an enhanced potency and reduced toxicity. This review article aims to demonstrate how bioinspired synthesis of chalcone derivatives can potentially introduce a new chemical space for exploitation for new drug discovery, justifying the title of this article. However, the focus remains on critical appraisal of synthesized chalcones and their derivatives for their bioactivities, linking to their interactions at the biomolecular level where appropriate, and revealing their possible mechanisms of action.

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Section: Antibacterial Activitymentioning

confidence: 99%

Chalcones: Synthetic Chemistry Follows Where Nature Leads

et al. 2021

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“…For S. aureus 1466, the MIC values of 3a – f ranged from 250 to 375 μM, which is similar to that for E. coli 780 ( Table 3 ), whereas the MBC values were much higher (1000 μM). The greater antibacterial activities of chalcones against E. coli 780 than S. aureus 1466 might be due to the thinness of the peptidoglycan layer in Gram-negative bacteria [ 28 , 46 , 47 , 48 ]. According to the MIC and MBC values, 3d showed the best antimicrobial activities against E. coli 780 and S. aureus 1466 compared to the other compounds among the series.…”

Section: Resultsmentioning

confidence: 99%

Photophysical Study and Biological Applications of Synthetic Chalcone-Based Fluorescent Dyes

et al. 2021

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A chalcone series (3a–f) with electron push–pull effect was synthesized via a one-pot Claisen–Schmidt reaction with a simple purification step. The compounds exhibited strong emission, peaking around 512–567 nm with mega-stokes shift (∆λ = 93–139 nm) in polar solvents (DMSO, MeOH, and PBS) and showed good photo-stability. Therefore, 3a–f were applied in cellular imaging. After 3 h of incubation, green fluorescence was clearly brighter in cancer cells (HepG2) compared to normal cells (HEK-293), suggesting preferential accumulation in cancer cells. Moreover, all compounds exhibited higher cytotoxicity within 24 h toward cancer cells (IC50 values ranging from 45 to 100 μM) than normal cells (IC50 value >100 μM). Furthermore, the antimicrobial properties of chalcones 3a–f were investigated. Interestingly, 3a–f exhibited antibacterial activities against Escherichia coli and Staphylococcus aureus, with minimum bactericidal concentrations (MBC) of 0.10–0.60 mg/mL (375–1000 µM), suggesting their potential antibacterial activity against both Gram-negative and Gram-positive bacteria. Thus, this series of chalcone-derived fluorescent dyes with facile synthesis shows great potential for the development of antibiotics and cancer cell staining agents.

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“…A series of five fluorinated chalcones (204–208) were evaluated for their antibacterial activity against Gram-positive and Gram-negative pathogenic bacterial strains using the agar diffusion method. The results showed that the compounds exhibited broad-spectrum activity against these pathogens ( Amole et al, 2019 ).…”

Section: Preclinical Pharmacological Activities Of Chalconesmentioning

confidence: 99%

Pharmacological Properties of Chalcones: A Review of Preclinical Including Molecular Mechanisms and Clinical Evidence

et al. 2021

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Chalcones are among the leading bioactive flavonoids with a therapeutic potential implicated to an array of bioactivities investigated by a series of preclinical and clinical studies. In this article, different scientific databases were searched to retrieve studies depicting the biological activities of chalcones and their derivatives. This review comprehensively describes preclinical studies on chalcones and their derivatives describing their immense significance as antidiabetic, anticancer, anti-inflammatory, antimicrobial, antioxidant, antiparasitic, psychoactive, and neuroprotective agents. Besides, clinical trials revealed their use in the treatment of chronic venous insufficiency, skin conditions, and cancer. Bioavailability studies on chalcones and derivatives indicate possible hindrance and improvement in relation to its nutraceutical and pharmaceutical applications. Multifaceted and complex underlying mechanisms of chalcone actions demonstrated their ability to modulate a number of cancer cell lines, to inhibit a number of pathological microorganisms and parasites, and to control a number of signaling molecules and cascades related to disease modification. Clinical studies on chalcones revealed general absence of adverse effects besides reducing the clinical signs and symptoms with decent bioavailability. Further studies are needed to elucidate their structure activity, toxicity concerns, cellular basis of mode of action, and interactions with other molecules.

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Synthesis, Characterization and Antibacterial Activities of New Fluorinated Chalcones

Cited by 24 publications

References 18 publications

Chalcones: Synthetic Chemistry Follows Where Nature Leads

Chalcones: Synthetic Chemistry Follows Where Nature Leads

Photophysical Study and Biological Applications of Synthetic Chalcone-Based Fluorescent Dyes

Pharmacological Properties of Chalcones: A Review of Preclinical Including Molecular Mechanisms and Clinical Evidence

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