Synthesis of New Piperazine Substituted Chalcone Sulphonamides as Antibacterial Agents

Tang, Yanling; Li, Minxin; Gao, Hui; Yang, Xiaobi; Mao, Zewei

doi:10.2174/1570179417666191227115207

Cited by 7 publications

(3 citation statements)

References 21 publications

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“…In another study using monomeric chalcone compounds, there was higher antibacterial activity in Gram-positive bacteria than the Gram-negative bacteria [ 59 ]. A screening method of chalcone derivatives against S. aureus , B. subtilis , E. coli , and P. aeruginosa showed increased lipophilic area, and the smaller molecular size of chalcones increased their antimicrobial activity [ 60 ].…”

Section: Basic Fragmentation Pathways Of Chalcones Are Obtained By Lo...mentioning

confidence: 99%

Pharmacotherapeutics Applications and Chemistry of Chalcone Derivatives

et al. 2022

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Chalcones have been well examined in the extant literature and demonstrated antibacterial, antifungal, anti-inflammatory, and anticancer properties. A detailed evaluation of the purported health benefits of chalcone and its derivatives, including molecular mechanisms of pharmacological activities, can be further explored. Therefore, this review aimed to describe the main characteristics of chalcone and its derivatives, including their method synthesis and pharmacotherapeutics applications with molecular mechanisms. The presence of the reactive α,β-unsaturated system in the chalcone’s rings showed different potential pharmacological properties, including inhibitory activity on enzymes, anticancer, anti-inflammatory, antibacterial, antifungal, antimalarial, antiprotozoal, and anti-filarial activity. Changing the structure by adding substituent groups to the aromatic ring can increase potency, reduce toxicity, and broaden pharmacological action. This report also summarized the potential health benefits of chalcone derivatives, particularly antimicrobial activity. We found that several chalcone compounds can inhibit diverse targets of antibiotic-resistance development pathways; therefore, they overcome resistance, and bacteria become susceptible to antibacterial compounds. A few chalcone compounds were more active than conventional antibiotics, like vancomycin and tetracycline. On another note, a series of pyran-fused chalcones and trichalcones can block the NF-B signaling complement system implicated in inflammation, and several compounds demonstrated more potent lipoxygenase inhibition than NSAIDs, such as indomethacin. This report integrated discussion from the domains of medicinal chemistry, organic synthesis, and diverse pharmacological applications, particularly for the development of new anti-infective agents that could be a useful reference for pharmaceutical scientists.

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Section: Basic Fragmentation Pathways Of Chalcones Are Obtained By Lo...mentioning

confidence: 99%

Pharmacotherapeutics Applications and Chemistry of Chalcone Derivatives

et al. 2022

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“…[1] They are also important intermediates for the production of a variety of biologically potent heterocyclic compounds. [2][3][4] Wide biological profile of chalcones containing a heterocyclic moiety include antiproliferative, [5] anticancer, [6] antioxidant, [7] antiviral, [8] antituberculosis, [9] antibacterial, [10] antifungal, [11] antihypertensive, [12] etc. 2,3-dihydrobenzofuran is an organic compound in which a dihydrofuran ring is fused with benzene.…”

Section: Introductionmentioning

confidence: 99%

DFT calculations on three 2,3‐dihydrobenzofuran linked chalcones: Structural, HOMO‐LUMO and spectroscopic (UV‐Vis and IR) interpretation

Adole

2023

Vietnam Journal of Chemistry

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Three chalcones with a 2,3‐dihydrobenzofuran linkage were analyzed by applying the density functional theory (DFT) and B3LYP approach with the 6‐311G(d,p) basis set in this report. Spectroscopic and theoretical analyses were used to examine the structures of these three chalcones. The chalcone molecules' HOMO‐LUMO energy was determined. Chemical reactivity parameters and molecular electrostatic surface potential (MESP) plots were obtained to gain useful insight into the distribution of charge density. The HOMO–LUMO gap of all three chalcones were calculated and discussed. The (E)‐3‐(2,3‐dihydrobenzofuran‐5‐yl)‐1‐phenylprop‐2‐en‐1‐one (DBPP) is discussed in detailed for the theoretical and experimental correlation. The captodative phenomenon appears to be the most polar molecule, with a dipole moment of 8.53 Debye. The decreased bandgap indicates that charge transfer occurs within the DBNPP molecule. When the solvent polarity is changed to DCM and DMSO from the gas phase, there is an event of a hyperchromic shift. The C19 carbon atom has the highest negative atomic charge while C21 is the carbon with the largest positive charge. From the MESP plots, we can conclude that the most electropositive region is located over the hydrogen atoms of the five‐membered ring, and the electronegative region is located over the oxygen atoms. Time‐dependent density functional theory (TD‐DFT) using B3LYP functional with 6‐311G(d,p) as basis set were used for the electronic absorption study in gas phase, dichloromethane and dimethyl sulfoxide. The UV‐Vis absorption peaks and fundamental vibrational wavenumbers were calculated and a good agreement between observed and theoretical results has been achieved.

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“…Sulfonamides are an imperative class of organic compounds which are an unremitting fascination for medicinal chemists and researchers due to their rich bioactive profile. − A brief literature review has demonstrated that several sulfonamide derivatives have been found to be the potent inhibitors of purinergic receptors. Gefapixant, a selective inhibitor of P2X3 receptor, is a sulfonamide derivative that is a promising remedy for chronic cough …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Sulfonamide Tethered (Hetero)aryl ethylidenes as Potential Inhibitors of P2X Receptors: A Promising Way for the Treatment of Pain and Inflammation

et al. 2021

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P2X receptors have the ability to regulate various physiological functions like neurotransmission, inflammatory responses, and pain sensation. Such physiological properties make these receptors a new target for the treatment of pain and inflammation. Several antagonists of P2X receptors have been studied for the treatment of neuropathic pain and neurodegenerative disorders but potency and selectivity are the major issues with these known inhibitors. Sulfonamide derivatives were reported to be potent inhibitors of P2X receptors. In this study, sulfonamide carrying precursor hydrazide was synthesized by a facile method that was subsequently condensed with methyl (hetero)arylketones to obtain a series of new (hetero)aryl ethylidenes. These compounds were screened for inhibitory potential against h-P2X2, h-P2X4, h-P2X5, and h-P2X7 receptors to find their potency and selectivity. Computational studies were performed to confirm the mode of inhibition as well as type of interaction between ligand and target site. In calcium signaling experiments, compound 6h was found to be the most potent and selective inhibitor of h-P2X2 and h-P2X7 receptors with IC50 ± standard error of the mean (SEM) values of 0.32 ± 0.01 and 1.10 ± 0.21 μM, respectively. Compounds 6a and 6c exhibited selective inhibition for h-P2X7 receptor, whereas 6e, 7a, and 7b expressed selective inhibitions toward h-P2X2 receptor that were comparable to the positive control suramin and pyridoxalphosphate-6-azophenyl-2′,4′-disulfonic acid (PPADS).

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Synthesis of New Piperazine Substituted Chalcone Sulphonamides as Antibacterial Agents

Cited by 7 publications

References 21 publications

Pharmacotherapeutics Applications and Chemistry of Chalcone Derivatives

Pharmacotherapeutics Applications and Chemistry of Chalcone Derivatives

DFT calculations on three 2,3‐dihydrobenzofuran linked chalcones: Structural, HOMO‐LUMO and spectroscopic (UV‐Vis and IR) interpretation

Synthesis of Sulfonamide Tethered (Hetero)aryl ethylidenes as Potential Inhibitors of P2X Receptors: A Promising Way for the Treatment of Pain and Inflammation

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