Microwave assisted synthesis of chalcone and its polycyclic heterocyclic analogues as promising antibacterial agents: In vitro, in silico and DFT studies

Khan, Salman A.; Asiri, Abdullah M.; Al-Ghamdi, Najat Saeed M.; Asad, Mohammad; Zayed, Mohie E. M.; Elroby, Shaaban A.; Aqlan, Faisal M.; Wani, Mohmmad Younus; Sharma, Kamlesh

doi:10.1016/j.molstruc.2019.04.046

Cited by 39 publications

(17 citation statements)

References 12 publications

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“…Moreover, it seems that the characteristic explained above is very common in antibacterial and antimicrobial compounds. An in-depth review of the bibliography reveals that several antibacterial and antibiotic (commercial and potential pharmaceutical) compounds have the HOMO-LUMO orbitals located in different molecular regions [64][65][66][67][68][69][70][71][72]. Thus, Compounds 2, 10, and 19, might be serious candidates for becoming pharmaceutical compounds.…”

Section: Drug-likeness Propertiesmentioning

confidence: 99%

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

2020

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Twenty-four cannabinoids active against MRSA SA1199B and XU212 were optimized at WB97XD/6-31G(d,p), and several molecular descriptors were obtained. Using a multiple linear regression method, several mathematical models with statistical significance were obtained. The robustness of the models was validated, employing the leave-one-out cross-validation and Y-scrambling methods. The entire data set was docked against penicillin-binding protein, iso-tyrosyl tRNA synthetase, and DNA gyrase. The most active cannabinoids had high affinity to penicillin-binding protein (PBP), whereas the least active compounds had low affinities for all of the targets. Among the cannabinoid compounds, Cannabinoid 2 was highlighted due to its suitable combination of both antimicrobial activity and higher scoring values against the selected target; therefore, its docking performance was compared to that of oxacillin, a commercial PBP inhibitor. The 2D figures reveal that both compounds hit the protein in the active site with a similar type of molecular interaction, where the hydroxyl groups in the aromatic ring of cannabinoids play a pivotal role in the biological activity. These results provide some evidence that the anti-Staphylococcus aureus activity of these cannabinoids may be related to the inhibition of the PBP protein; besides, the robustness of the models along with the docking and Quantitative Structure–Activity Relationship (QSAR) results allow the proposal of three new compounds; the predicted activity combined with the scoring values against PBP should encourage future synthesis and experimental testing.

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Section: Drug-likeness Propertiesmentioning

confidence: 99%

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

2020

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“…In recent years, scientists have been interested in the use of small organic molecules, including heterocyclic compounds, as promising therapeutic substances [ 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. Literature data from our review indicate that 1,3,4-thiadiazole derivatives and intermediates in their synthesis, 1,4-disubstituted thiosemicarbazides, are commonly reported as promising antimicrobial agents [ 1 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antibacterial Evaluations and In Silico Studies of Novel Thiosemicarbazides and 1,3,4-Thiadiazoles

et al. 2022

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The emergence of drug-resistant bacterial strains continues to be one of the major challenges of medicine. For this reason, the importance of searching for novel structures of antibacterial drugs chemically different from the currently known antibiotics is still of great importance. In this study, we synthesized the thiosemicarbazide and 1,3,4-thiadiazole derivatives and tested them for antibacterial activity. In in vitro tests, we examined the activity of the synthesized substances against Gram-positive and Gram-negative bacteria strains. While all 1,3,4-thiadiazoles tested lacked significant activity, the antimicrobial response of the thiosemicarbazides was moderate and it was also dependent on the type and position of the substituent on the phenyl ring. The highest activity towards all Gram-positive bacteria strains was shown by all three linear compounds containing the trifluoromethylphenyl group in the structure. The MIC (minimum inhibitory concentration) values were in the range of 3.9–250 µg/mL. Additionally, we try to explain the mechanism of the antibacterial activity of the tested compounds using the molecular docking to DNA gyrase and topoisomerase IV, following previous reports on the molecular basis of the activity of thiosemicarbazides. Docking simulations allow the purposing dual mechanism of the antibacterial activity of the synthesized compounds through inhibition of topoisomerase IV DNA gyrase with the moderate prevalence of the topoisomerase pathway.

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“…[5][6][7][8] For this reason, chalcones and chalcone-like compounds are highly valuable compounds for organic chemists and they can be used as a key or building block in achieving molecular diversity. [9][10][11][12] Among the reactions of the chalcones, 1,4-Michael addition is undoubtedly the most important. [13] The chalcones are a very good Michael acceptor and therefore carbon-carbon, [14] carbonnitrogen, [15] carbon-oxygen [16] and carbon-sulfur [17] bond forma-tions can be realized very easily via the 1,4-Michael addition from adding nucleophiles to chalcones.…”

Section: Introductionmentioning

confidence: 99%

Michael/Michael Addition Cascade of 2‐Benzylidene‐1‐indanones with Chalcones: Synthesis and Biological Evaluations of Novel Polycyclic Compounds

et al. 2021

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A series of novel racemic 2-aryloyl-1,3-diaryl-2,3,3a,8a-tetrahydrocyclopenta[a]inden-8(1H)-one derivatives were synthesized from KOtBu mediated Michael/Michael addition reaction of 2benzylidene-1-indanones with chalcones in high yields. This method provides an efficient route for the synthesis of a new class of polycyclic compounds have five stereo centers. The obtained polycyclic compounds were evaluated for the antimicrobial and anticancer activities against fifteen microorganism and three cell lines. The compound 3 r have the best activity value against the cells (MCF-7 IC 50 = 18.01 � 0.39 μg/ mL) (MDA-MB-231 IC 50 = 18.78 � 1.75 μg/mL) (MCF-10 A IC 50 = 31.31 � 0.05 μg/mL).

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Microwave assisted synthesis of chalcone and its polycyclic heterocyclic analogues as promising antibacterial agents: In vitro, in silico and DFT studies

Cited by 39 publications

References 12 publications

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

Modelling the Anti-Methicillin-Resistant Staphylococcus Aureus (MRSA) Activity of Cannabinoids: A QSAR and Docking Study

Design, Synthesis, Antibacterial Evaluations and In Silico Studies of Novel Thiosemicarbazides and 1,3,4-Thiadiazoles

Michael/Michael Addition Cascade of 2‐Benzylidene‐1‐indanones with Chalcones: Synthesis and Biological Evaluations of Novel Polycyclic Compounds

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