Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach

Konidala, Sathish Kumar; Kotra, Vijay; Danduga, Ravi Chandra Sekhara Reddy; Kola, Phani Kumar; Bhandare, Richie R.; Shaik, Afzal B.

doi:10.1016/j.arabjc.2021.103154

Cited by 32 publications

(20 citation statements)

References 74 publications

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“…Whereas that of ascorbic acid was 2.17 µg/mL. These results are almost identical to those described in the literature [25][26][27][28][29]. At a concentration of 10 µg/mL, the inhibition percentage of the third chalcone was 87.71%.…”

Section: Antioxidant Activitysupporting

confidence: 90%

Synthesis, In-vitro antibacterial and antioxidant activity of chalcone derivatives

Mulula¹,

Bouzina²,

Mambu³

et al. 2022

GSC Biol. Pharm. Sci.

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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-hydroxyphenyl) prop-2-en-1-one showed excellent activity against Bacillus subtilis with Minimum Inhibitory Concentration (MIC) of 62.5 µg/mL which is similar to that of the standard (Ampicillin) against the same bacterial strain. Antioxidant activity evaluated using 2,2-diphenyl2-picryl- hydrazyle ( DPPH) revealed that all the synthesized chalcones showed an antioxidant activity with IC50 values of 8.22; 6.89 and 3.39 µg/mL for (E)-1-(2-hydroxyphenyl)-3-(4-hydroxyphenyl) prop-2-en-1-one, (E)-1-(2-hydroxyphenyl)-3-(4-methoxyphenyl) prop-2-en-1-one and (E)-3-(3, 4-dimethoxyphenyl)-1-(2-hydroxyphenyl) prop-2-en-1-one, respectively. These values are closer to that of ascorbic acid used as a standard. The results suggest that the synthesized chalcones, especially the (E)-3-(3, 4-dimethoxyphenyl)-1-(2-hydroxyphenyl) prop-2-en-1-one could be used, after in vivo and clinical tests, like antibacterial and antioxidant supplement or even replace current drug therapies.

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Section: Antioxidant Activitysupporting

confidence: 90%

Synthesis, In-vitro antibacterial and antioxidant activity of chalcone derivatives

Mulula¹,

Bouzina²,

Mambu³

et al. 2022

GSC Biol. Pharm. Sci.

View full text Add to dashboard Cite

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“…All compounds have been assessed for their ADMET profile in ADMET Predictor version 10.4 provided by the Simulation Plus software package [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 ...…”

Section: Resultsmentioning

confidence: 99%

“…Since the molecular hybridization approach may result in compounds that inhibit more than one target, we set up our investigation to discover novel antibacterial and antifungal agents based on this rationale [ 44 ].…”

Section: Introductionmentioning

confidence: 99%

N-Derivatives of (Z)-Methyl 3-(4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylates as Antimicrobial Agents—In Silico and In Vitro Evaluation

et al. 2023

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Herein, we report the experimental evaluation of the antimicrobial activity of seventeen new (Z)-methyl 3-(4-oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylate derivatives. All tested compounds exhibited antibacterial activity against eight Gram-positive and Gram-negative bacteria. Their activity exceeded those of ampicillin as well as streptomycin by 10–50 fold. The most sensitive bacterium was En. Cloacae, while E. coli was the most resistant one, followed by M. flavus. The most active compound appeared to be compound 8 with MIC at 0.004–0.03 mg/mL and MBC at 0.008–0.06 mg/mL. The antifungal activity of tested compounds was good to excellent with MIC in the range of 0.004–0.06 mg/mL, with compound 15 being the most potent. T. viride was the most sensitive fungal, while A. fumigatus was the most resistant one. Docking studies revealed that the inhibition of E. coli MurB is probably responsible for their antibacterial activity, while 14a–lanosterol demethylase of CYP51Ca is involved in the mechanism of antifungal activity. Furthermore, drug-likeness and ADMET profile prediction were performed. Finally, the cytotoxicity studies were performed for the most active compounds using MTT assay against normal MRC5 cells.

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“…A chalcone derived from carbazoles was assayed for antibacterial activity against two gram-positive ( S. aureus and B. subtilis ) and two gram-negative bacterial strains (E. coli and K. pneumonia) and antifungal activity against Fusarium oxysporum, Aspergillus niger, and Aspergillus flavus (Ashok et al 2016 ). Konidala et al ( 2021 ) found that the antimicrobial screening of the chalcone compounds showed potent antifungal activity with MIC value of 10 µM and 11 µM against Aspergillus niger .…”

Section: Resultsmentioning

confidence: 99%

Novel eco-friendly [1,2,4]triazolo[3,4-a]isoquinoline chalcone derivatives efficiency against fungal deterioration of ancient Egyptian mummy cartonnage, Egypt

et al. 2023

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Fungal deterioration is one of the major factors that significantly contribute to mummy cartonnage damage. Isolation and molecular identification of thirteen fungal species contributing to the deterioration of ancient Egyptian mummy cartonnage located in El-Lahun regions, Fayoum government, Egypt was performed. The most dominant deteriorated fungal species are Aspergillus flavus (25.70%), Aspergillus terreus (16.76%), followed by A. niger (13.97%). A newly synthesized series of tetrahydro-[1,2,4]triazolo[3,4-a]isoquinoline chalcone derivatives were synthesized and evaluated for their antifungal activities in vitro against the isolated deteriorated fungal species (Aspergillus flavus, A. niger, A. terreus, Athelia bombacina, Aureobasidium iranianum, Byssochlamys spectabilis, Cladosporium cladosporioides, C. ramotenellum, Penicillium crustosum, P. polonicum, Talaromyces atroroseus, T. minioluteus and T. purpureogenus). The most efficient chalcone derivatives are new chalcone derivative numbers 9 with minimum inhibitory concentration (MIC) ranging from 1 to 3 mg/mL followed by chalcone derivatives number 5 with MIC ranging from 1 to 4 mg/mL.

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Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach

Cited by 32 publications

References 74 publications

Synthesis, In-vitro antibacterial and antioxidant activity of chalcone derivatives

Synthesis, In-vitro antibacterial and antioxidant activity of chalcone derivatives

N-Derivatives of (Z)-Methyl 3-(4-Oxo-2-thioxothiazolidin-5-ylidene)methyl)-1H-indole-2-carboxylates as Antimicrobial Agents—In Silico and In Vitro Evaluation

Novel eco-friendly [1,2,4]triazolo[3,4-a]isoquinoline chalcone derivatives efficiency against fungal deterioration of ancient Egyptian mummy cartonnage, Egypt

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