Designing heterocyclic chalcones, benzoyl/sulfonyl hydrazones: An insight into their biological activities and molecular docking study

Aktar, Bedriye Seda Kurşun; Sıcak, Yusuf; Tok, Tuğba Taşkın; Oruç‐Emre, Emine Elçin; Yağlıoğlu, Ayşe Şahin; Karaküçük‐İyidoğan, Ayşegül; Demirtaş, İbrahim

doi:10.1016/j.molstruc.2020.128059

Cited by 24 publications

(10 citation statements)

References 43 publications

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“…As an improvement of such studies, Shruthi et al have recently reported that such compounds were found to be active against bacterial strains including Acinetobacter baumannii, Escherichia coli and Staphylococcus aureus. [35] MIC (µg/mL) In the same area of research, Rao [51], Kursun [52] and Fahmy [53] have performed the synthesis of various analogues of derivatives 56a-d demonstrating also moderate to good antibacterial and antifungal activities against Gram-positive bacteria and fungi with diameter of inhibition ranging from 0 to 17 mm depending on the considered microorganisms (Table 20).…”

Section: Methodsmentioning

confidence: 99%

Frontiers in Anti-Infective Drug Discovery: Volume 7

2018

Frontiers in Anti-Infective Drug Discovery

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Antimicrobial resistance of Gram-negative bacteria is a major concern and no new classes of antibiotics that are effective against this type of bacteria have been discovered since the 1960s. During the last decades, multiple approaches have been developed to combat such a bacterial resistance. However, the combination of antibiotic resistance mechanisms by bacteria and the limited number of effective antibiotics available, decreases the number of the interventions for the treatment of current bacterial infections. The solution to emerging antibiotic resistance will likely involve new therapies or new classes of antibacterial agents. For a few years now, there was a real interest in the design and synthesis of hydrazones possessing an azometine -NHN=CH-proton and constituting an important class of compounds for new drugs development as anticonvulsants, antidepressants, antitumoral agents. In this context, the design and antimicrobial evaluation of hydrazone derivatives has constituted one of the new strategies developed to fight bacterial resistance. As pointed out the range of biological activities is very broad, and this review will deal exclusively with the synthesis and use of hydrazones as antimicrobial agents and will not cover the other biological properties already well depicted in literature. Thus, we will report herein the scope and limitation of such an approach providing numerous examples demonstrating structure-activity relationships and potent interesting antimicrobial activities against both fungi, Gram-positive and/or Gram-negative bacteria.

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Section: Methodsmentioning

confidence: 99%

Frontiers in Anti-Infective Drug Discovery: Volume 7

2018

Frontiers in Anti-Infective Drug Discovery

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“…Chalcones, first used by Kostanecki , are a class of natural flavonoid derivatives called 1,3‐diphenyl‐2‐propen‐1‐one containing two aryl groups attached to the α,β ‐unsaturated ketone 54 . Although there are similar methods in the literature using different catalysts, the simplest procedure for synthesizing chalcones is the Claisen–Schmidt condensation of benzaldehydes, which are dissolved in methanol or ethanol under basic or acidic conditions with aromatic ketones 55,56 . It is known that chalcones and their heterocyclic derivatives have pharmacological activities such as anticancer, antidiabetic, anti‐inflammatory, antioxidant, antibacterial, antifungal, antimalarial, antiulcer, antiviral, and as well as inhibition activity of various enzymes 57–67 …”

Section: Introductionmentioning

confidence: 99%

“…54 Although there are similar methods in the literature using different catalysts, the simplest procedure for synthesizing chalcones is the Claisen-Schmidt condensation of benzaldehydes, which are dissolved in methanol or ethanol under basic or acidic conditions with aromatic ketones. 55,56 It is known that chalcones and their heterocyclic derivatives have pharmacological activities such as anticancer, antidiabetic, anti-inflammatory, antioxidant, antibacterial, antifungal, antimalarial, antiulcer, antiviral, and as well as inhibition activity of various enzymes. [57][58][59][60][61][62][63][64][65][66][67] While researchers have long tussled to develop particular compounds against a specific target, it has often been found that the "one drug-one target" approach shows no clinical efficacy in multifactorial disorders.…”

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Chalcones bearing nitrogen‐containing heterocyclics as multi‐targeted inhibitors: Design, synthesis, biological evaluation and molecular docking studies

Sıcak

Kekeçmuhammed

Karaküçük‐İyidoğan

et al. 2023

J of Molecular Recognition

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In this work, a series of chalcones (1a–d, 2a–d, 3a–d, 4a–d, and 5a–d) were designed and synthesized by Claisen–Schmidt condensation. Also, their chemical structures were elucidated using UV–Vis, FT IR, 1H NMR, 13C NMR, MS spectral data, and elemental analyses. Subsequently, the anticholinesterase, tyrosinase, urease inhibitory activities and antioxidant activities of all chalcones were evaluated. The inhibitory potential of all chalcones in terms of IC50 value was observed to range from 7.18 ± 0.43 to 29.62 ± 0.30 μM against BChE by comparing with Galantamine (IC50 46.06 ± 0.10 μM) as a reference drug. Also, compounds 2c, 3c, 4c, 4b, and 4d exhibited high anticholinesterase activity against both AChE and BChE enzymes. The tyrosinase inhibitory activity results revealed that three compounds (IC50 1.75 ± 0.83 μM for 2b, IC50 2.24 ± 0.11 μM for 3b, and IC50 1.90 ± 0.64 μM for 4b) displayed good inhibitory activity against tyrosinase compared with kojic acid (IC50 0.64 ± 0.12 μM). In addition, other different three chalcones (IC50 22.34 ± 0.25 μM for 2c, IC50 20.98 ± 0.08 μM for 3c, and IC50 18.26 ± 0.13 μM for 4c) showed excellent inhibitory activity against the urease by comparing with thiourea (IC50 23.08 ± 0.19 μM). Compounds 3c and 4c showed the best potency in all antioxidant activity tests. In light of these findings, the structure–activity relationship for compounds was also described. Furthermore, molecular modeling studies, including molecular docking, absorption, distribution, metabolism, excretion, and toxicity (ADMET), and pharmacophore analyses of compounds, gave important information about the interactions and drug‐likeness properties. As a result, all chalcones exhibited suitable ADMET findings, predicting good oral bioavailability.

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“…The chalcones have inhibitory effects against enzymes such as xanthine oxidase, 1 protein tyrosine kinase, 2 quinone reductase, 3 tyrosinase, 4 mammalian alpha-amylase 5 , monoamine oxidase, 6 pyruvate kinase M2 (PKM2), 7 carbonic anhydrase I (CAI), 7 heme oxygenase, 8 carbonic anhydrase II (CAII), 7 aldose reductase, acetylcholinesterase (AChE), 9 α-amylase and αglucosidase, 10 butyrylcholinesterase (BChE). 9 Xanthine oxidase inhibitor reduces uric acid production in humans and inhibits xanthine oxidase. Xanthine oxidase (XO) is a type of enzyme that is a form of xanthine oxidoreductase and produces reactive oxygen species.…”

Section: Introductionmentioning

confidence: 99%

Benzoik Asitli Kalkonların Ksantin Oksidaz İnhibitörü Üzerine Etkisinin İncelenmesi

Aktar¹,

Adem

Oruç‐Emre

2022

International Journal of Chemistry and Technology

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Inhibitors of xanthine oxidase (XO) are effective and most major therapeutic drugs for the management of gout. Chalcone compounds are important in terms of biological activity and have great importance in enzyme studies in recent years. In the presented study, the effects of some chalcones on the enzyme were tested in vitro by the spectrophotometric method. Compounds showed an inhibitory effect between 7.21±0.07 and 13.78±0.13 µM IC50 values. The conformations and interactions of the compounds in the active site of the enzyme were determined by the molecular docking method using Molegro Virtual Docker software. Molecular modeling studies show that the B ring of chalcones has a significant contribution to the inhibition effect on the XO enzyme. The presented study suggests that chalcones may be a potential inhibitory group for XO.

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Designing heterocyclic chalcones, benzoyl/sulfonyl hydrazones: An insight into their biological activities and molecular docking study

Cited by 24 publications

References 43 publications

Frontiers in Anti-Infective Drug Discovery: Volume 7

Frontiers in Anti-Infective Drug Discovery: Volume 7

Chalcones bearing nitrogen‐containing heterocyclics as multi‐targeted inhibitors: Design, synthesis, biological evaluation and molecular docking studies

Benzoik Asitli Kalkonların Ksantin Oksidaz İnhibitörü Üzerine Etkisinin İncelenmesi

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