Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones

Govender, Hogantharanni; Mocktar, Chunderika; Kumalo, Hezekiel M.; Koorbanally, Neil A.

doi:10.1080/10426507.2019.1618298

Cited by 23 publications

(19 citation statements)

References 41 publications

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“…In the study, the antidiabetic potential of novel thiosemicarbazones derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11) Note: The cells were exposed to various concentrations of the compounds ranging between 0.1 to 100 μM and the cytotoxicity was examined using the XTT assay.…”

Section: Antidiabetic Potentialmentioning

confidence: 99%

“…Thiosemicarbazones are an important class of organic chemistry with similar biological and medicinal effects. They have been reported having numerous medicinal and biological activities such as antibacterial, [1,2] antioxidant, [3][4][5] antimicrobial, [6] anti-inflammatory, [7] anticancer, [8,9] antituberculosis, [10] enzyme inhibition, [11] cytotoxicity and antifungal activity. [12,13] Acetylcholinesterase (E.C.3.1.1.7, AChE, acetylhydrolase) is an enzyme from the hydrolase group that hydrolyzes the neurotransmitter acetylcholine.…”

Section: Introductionmentioning

confidence: 99%

“…The difference between the interaction types and energies of a series of drug candidate molecules can be easily distinguished. [27] In the present study, we describe the synthesis, structure characterization, evaluation of novel thiosemicarbazone derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11) as effective anticancer agents and carbonic anhydrase enzyme inhibitors (Scheme 1). Moreover, we examine the activity with the revealed metabolic enzymes of studied molecules by molecular docking studies.…”

Section: Introductionmentioning

confidence: 99%

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Potential thiosemicarbazone‐based enzyme inhibitors: Assessment of antiproliferative activity, metabolic enzyme inhibition properties, and molecular docking calculations

Yakan

Koçyiğit

Muğlu

et al. 2022

J Biochem & Molecular Tox

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A new series of thiosemicarbazone derivatives (1–11) were prepared from various aldehydes and isocyanates with high yields and practical methods. The structures of these compounds were elucidated by Fourier transform infrared, 1H‐nuclear magnetic resonance (NMR), 13C‐NMR spectroscopic methods and elemental analysis. Cytotoxic effects of target compounds were determined by 2,3‐bis‐(2‐methoxy‐4‐nitro‐5‐sulfophenyl)‐2H‐tetrazolium‐5‐carboxanilide assay and compound 1 showed significant cytotoxic activity against both MCF‐7 and MDA‐MB‐231 cells, with half‐maximal inhibitory concentration values of 2.97 μM and 6.57 μM, respectively. Moreover, in this study, the anticholinergic and antidiabetic potentials of these compounds were investigated. To this aim, the effect of the newly synthesized thiosemicarbazone derivatives on the activities of acetylcholinesterase (AChE) and αglycosidase (α‐Gly) was evaluated spectrophotometrically. The title compounds demonstrated high inhibitory activities compared to standard inhibitors with Ki values in the range of 122.15–333.61 nM for α‐Gly (Ki value for standard inhibitor = 75.48 nM), 1.93–12.36 nM for AChE (Ki value for standard inhibitor = 17.45 nM). Antiproliferative activity and enzyme inhibition at the molecular level were performed molecular docking studies for thiosemicarbazone derivatives. 1M17, 5FI2, and 4EY6, 4J5T target proteins with protein data bank identification with (1–11) compounds were docked for anticancer and enzyme inhibition, respectively.

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Section: Antidiabetic Potentialmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Potential thiosemicarbazone‐based enzyme inhibitors: Assessment of antiproliferative activity, metabolic enzyme inhibition properties, and molecular docking calculations

Yakan

Koçyiğit

Muğlu

et al. 2022

J Biochem & Molecular Tox

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“…Acetylation of the appropriate anilines 89 with acetic anhydride in acetic acid to achieve the corresponding anilides 90 , which undergo Vilsmeier–Haack reaction to give the substituted‐2‐chloro‐3‐formylquinolines 91 [55–57]. Treatment of compound 91 with dilute HCl [56,58] or AcOH 70% [57] gave the 3‐formyl quinolines 92 , which condensed with malonic acid 93 in ethanol in the presence of piperidine to give the cinnamic acids 94 (Scheme 22) [59,60].…”

Section: Synthesis and Reactivitymentioning

confidence: 99%

Synthesis and reactivity of thieno[2,3‐b]quinoline derivatives (Part II)

Salem

Abu‐Hashem

Abdelgawad

et al. 2021

Journal of Heterocyclic Chem

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“…In this context, the antimicrobial importance of polyheterocyclic systems such as 2‐quinolones is well established. The 2‐quinolone moiety is among the most widely used synthetic scaffolds that researchers have used for successful design of new antimicrobial agents [11–25] . One useful strategy has been to create hybrid molecules [26] using two different pharmacophoric moieties with antimicrobial effects.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, in vitro and in silico Characterization of 2‐Quinolone‐L‐alaninate‐1,2,3‐triazoles as Antimicrobial Agents

et al. 2022

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Due to the ever‐increasing antimicrobial resistance there is an urgent need to continuously design and develop novel antimicrobial agents. Inspired by the broad antibacterial activities of various heterocyclic compounds such as 2‐quinolone derivatives, we designed and synthesized new methyl‐(2‐oxo‐1,2‐dihydroquinolin‐4‐yl)‐L‐alaninate‐1,2,3‐triazole derivatives via 1,3‐dipolar cycloaddition reaction of 1‐propargyl‐2‐quinolone‐L‐alaninate with appropriate azide groups. The synthesized compounds were obtained in good yield ranging from 75 to 80 %. The chemical structures of these novel hybrid molecules were determined by spectroscopic methods and the antimicrobial activity of the compounds was investigated against both bacterial and fungal strains. The tested compounds showed significant antimicrobial activity and weak to moderate antifungal activity. Despite the evident similarity of the quinolone moiety of our compounds with fluoroquinolones, our compounds do not function by inhibiting DNA gyrase. Computational characterization of the compounds shows that they have attractive physicochemical and pharmacokinetic properties and could serve as templates for developing potential antimicrobial agents for clinical use.

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Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones

Cited by 23 publications

References 41 publications

Potential thiosemicarbazone‐based enzyme inhibitors: Assessment of antiproliferative activity, metabolic enzyme inhibition properties, and molecular docking calculations

Potential thiosemicarbazone‐based enzyme inhibitors: Assessment of antiproliferative activity, metabolic enzyme inhibition properties, and molecular docking calculations

Synthesis and reactivity of thieno[2,3‐b]quinoline derivatives (Part II)

Design, Synthesis, in vitro and in silico Characterization of 2‐Quinolone‐L‐alaninate‐1,2,3‐triazoles as Antimicrobial Agents

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