BDDE-Inspired Chalcone Derivatives as New Antimicrobial Adjuvants (original) (raw)
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BDDE-Inspired Chalcone Derivatives to Fight Bacterial and Fungal Infections
Marine Drugs
The growing number of infectious diseases around the world threatens the effective response of antibiotics, contributing to the increase in antibiotic resistance seen as a global health problem. Currently, one of the main challenges in antimicrobial drug discovery is the search for new compounds that not only exhibit antimicrobial activity, but can also potentiate the antimicrobial activity and revert antibiotics’ resistance, through the interference with several mechanisms, including the inhibition of efflux pumps (EPs) and biofilm formation. Inspired by macroalgae brominated bromophenol BDDE with antimicrobial activity, a series of 18 chalcone derivatives, including seven chalcones (9–15), six dihydrochalcones (16–18, and 22–24) and five diarylpropanes (19–21, and 25 and 26), was prepared and evaluated for its antimicrobial activity and potential to fight antibiotic resistance. Among them, chalcones 13 and 14 showed promising antifungal activity against the dermatophyte clinical s...
The Benefits of Chalcone and Its Derivatives as Antibacterial Agents: A Review
BIO Web of Conferences
Chalcone is a secondary metabolite compound found in plants. Chalcones contain two aryl rings, namely ring A and B which connected to the α,β unsaturated ketones. Chalcone derivatives are synthesized by various substituent groups in both rings, as well as the types of rings. These variations make chalcone and its derivatives, have interesting bioactivity, one of which is antibacterial. This review is considered the chalcone-derived compounds that have antibacterial bioactivity, including methoxy, hydroxy, prenyl, and halogen groups in ring A or B. Besides, there are two forms of these rings as well such as pyrroly l-furany l-chalcones and indoly l-thiopheny l-chalcone. We hope this review is useful for the development of the synthesis of organic compounds and the discovery of new drug design.
New chalcone derivatives as potential antimicrobial and antioxidant agent
Scientific Reports
Seven chalcone derivatives were synthesized by the Claisen-Schmidt condensation. The structures of the compounds were confirmed by spectral data (Ultraviolet/visible, infrared, nuclear magnetic resonance and mass spectroscopy). The compounds were tested for their in silico and in vitro antimicrobial and antioxidant activities. The molecular docking assessments showed that all the compounds exhibited good binding affinity with the target microorganism proteins but, compounds 6e and 6g showed better binding affinity compared with the standards. The antimicrobial test revealed that all the compounds screened were active against Staphylococcus aureus and Bacillus subtilis and had minimum inhibitory concentrations (MIC) between 0.4 and 0.6 mg/mL. Compounds 6a, 6c and 6d had moderate activities on Salmonella typhi. Compounds 6b and 6c had moderate activity on Escherichia coli. Compound 6c had moderate activity on Aspergillus niger while compounds 6a and 6e had poor activity. All the compo...
Synthesis, In-vitro antibacterial and antioxidant activity of chalcone derivatives
GSC Biological and Pharmaceutical Sciences
In the face of the emergence of bacteria resistant to common antibacterials and excessive accumulation of free radicals that can cause several diseases, it is important to look for new antibacterials and antioxidants. The goal of this work was to synthesize three chalcones derivatives by the Claisen-Schmidt condensation and then evaluate their antibacterial and antioxidant activities. The structure of these 3 compounds has been determined by NMR (1H and 13C) spectroscopy. The in vitro antibacterial activity assessed by Microdilution methods, was tested against Gram positive bacteria (Staphylococcus aureus and Bacillus subtilis) and gram negative bacteria (Escherichia coli and Pseudomonas aeruginosa) at different concentrations ranging from 7.82 to 1000 µg/mL. All three synthesized chalcones showed good antibacterial activity against gram positive and negative bacteria used with a range of MIC ranging from 62.50 to 1000 µg/mL. However, the (E)-3-(3, 4-dimethoxyphenyl)-1-(2-hydroxyphe...
In-Vitro Antibacterial Activity of Some Substituted Chalcone Derivatives
The chalcones, are precursor of open chain flavonoids and isoflavonoids which are present in several nature products, and their derivatives have been showed increasing attention due to numerous potential biological and pharmacological activities such as anti-inflammatory, anti-tuberculosis, anti-fungal, anti-malarial, antimicrobial, anti-bacterial, anti-cancer. Changes in their structure have offered a high degree of diversity that has proven useful for the development of new medicinal agents having improved potency and lesser toxicity. In this report we present the synthesis of a series of α,βunsaturated carbonyl compounds (chalcones), and also report the evaluation of this synthesis by Eco Scale, which shows anti-bacterial activity of some selected pathogens according to their efficacy by semi quantitative analysis base on safety, economic and ecological features. Chalcones were synthesized via Claisen Schmidt condensation reaction with acetophenone and p-hydroxy benzaldehyde, m-nitro benzaldehyde, p-chloro benzaldehyde, p-dimethyl amino benzaldehyde, aqueous NaOH in ehanol, at room temperature. After completion of the reaction, the mixture was filtered to collect the precipitates and purification by recrystallization affords the pure chalcones. The green chemistry foments the use of auxiliary substances should be unnecessary wherever possible and innocuous when used, due to we use ethanol instead methanol, because it obtained from renewable resources.
Asian Journal of Chemistry, 2021
Several chalcones viz. 1,3-diaryl-2-propane-1-one (1a), 3-(4-hydroxy phenyl)-1-phenyl-2-propane-1- one (1b), 3-(4-amino-phenyl)-1-phenyl-2-propane-1-one (1c) and their derivatives 2-ethoxy-4,6- diphenyl-4H-pyran-3-carboxylic acid ethyl ester (2a), 4-(4-hydroxy-phenyl)-7,7-dimethyl-2-phenyl- 4,6,7,8-tetrahydro-chromen-5-one (2b) and 7-(4-amino-phenyl)-5-phenyl-1,5-dihydropyrano[2,3- d]pyrimidine-2,4-dione (2c ) have been synthesized following both conventional and microwave irradiation methods. The structures of the isolated compounds were elucidated on the basis of UV-visible, FTIR, 1H NMR spectral data. The antimicrobial results showed some remarkable facts about the structure–activity relationship, which states that the electronic atmosphere around the chalcone derivative moieties and substituents considerably affect the antimicrobial potential of the synthesized compounds. Theoretical calculation as well as antimicrobial activity of the compounds were also studied.