Synthesis of Novel Substituted 1,3-diarylpropenone Derivatives and their In Vitro Cytotoxic Activity

Ivanova, Yordanka; Momekov, Georgi; Petrov, Ognyan

doi:10.2174/1570180810906050353

Cited by 5 publications

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“…In continuation of our previous studies on the synthesis of heterocyclic chalcone derivatives with benzoxazolone [5] or benzothiazolone ring [6][7][8], in this work we report the preparation of a novel (E)-3-methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone. The compound consists of thiophene and benzothiazolone heterocycles, connected via α,β-unsaturated carbonyl system, a key framework of chalcones.…”

Section: Introductionmentioning

confidence: 92%

(E)-3-Methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone

Ivanova

Gerova

Chanev

et al. 2016

Molbank

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Section: Introductionmentioning

confidence: 92%

(E)-3-Methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone

Ivanova

Gerova

Chanev

et al. 2016

Molbank

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“…In a very limited number of studies, some chalcones bearing 2(3 H )‐benzoxazolone with different substituents on the phenyl ring were reported with their strong cytotoxic activities. [ 3,58,61,62 ] Both the selective and strong anticancer activities of these compounds pointed out the importance of this chemical moiety in designing new chalcone compounds for possible drug candidate molecules. Thus, we chose the chalcone structure bearing the 2(3 H )‐benzoxazolone heterocycle as the main chemical skeleton for further investigation.…”

Section: Introductionmentioning

confidence: 99%

New halogenated chalcones with cytotoxic and carbonic anhydrase inhibitory properties: 6‐(3‐Halogenated phenyl‐2‐propen‐1‐oyl)‐2(3H)‐benzoxazolones

Bilginer

Gül

Erdal

et al. 2020

Archiv der Pharmazie

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In this study, novel halogenated chalcones, 6-(3-halogenated phenyl-2-propen-1-one)-2(3H)-benzoxazolones (2a-n), were synthesized for the first time (except 2a), and their chemical structures were characterized by 1 H nuclear magnetic resonance (NMR), 13 C NMR, and high-resolution mass spectrometry spectra. Cytotoxic activities and carbonic anhydrase (CA) inhibitory effects of the compounds were studied to identify new possible drug candidate molecules. Cytotoxicity results pointed out that compound 2m, 6-[3-(3-bromophenyl)-2-propenoyl]-2(3H)-benzoxazolone, had the highest cytotoxicity (CC 50 ) and potency selectivity expression (PSE) values. Thus, compound 2m can be considered as a lead compound of the series in terms of cytotoxicity. When the CA inhibition results of the compounds were evaluated, it was found that the K i values of the compounds ranged from 30.5 ± 11.3 to 65.5 ± 25.6 µM toward hCA I, and they ranged from 7.3 ± 1.8 to 58.8 ± 12.3 µM toward hCA II. However, the K i values of the reference drug, acetazolamide (AZA), were 30.2 ± 7.8 and 4.4 ± 0.6 μM toward hCA I and hCA II, respectively. According to the results obtained, compounds 2a-n had lower K i values than AZA, whereas compounds 2a, 2b, 2e-g, 2l, and 2n had similar K i values, compared with AZA. So, the compounds 2a, 2b, 2e-g, 2l, and 2n can be considered as lead molecules of this series for further considerations.

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“…Some chalcones bearing 2(3H)-benzoxazolone were reported with strong cytotoxic activity 33,34 . However, there is a very limited number of studies about them.…”

Section: Introductionmentioning

confidence: 99%

“…One of them is Ivanova and coworkers' study. They reported antileukemic effects of benzoxazolone derived chalcones on BV-173 cell-line by inducing apoptotic cell death 33 . The fact that these compounds showed selective and strong anticancer activity pointed out the importance of benzoxazolone bearing chalcone molecules in designing new anticancer candidate molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, cytotoxicities, and carbonic anhydrase inhibition potential of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

Bilginer

Gül

Erdal

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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In this study, new chalcone compounds having the chemical structure of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones (1-8) were synthesised and were characterised by 1 H-NMR, 13 C-NMR, and HRMS spectra. Cytotoxic and carbonic anhydrase (CA) inhibitory effects of the compounds were investigated. Cytotoxicity results pointed out that compound 4, 6-[3-(4-trifluoromethylphenyl)-2-propenoyl]-3H-benzoxazol-2-one, showed the highest cytotoxicity (CC 50) and potency-selectivity expression (PSE) value, and thus can be considered as a lead compound of this study. According to the CA inhibitory results, IC 50 values of the compounds 1-8 towards hCA I were in the range of 29.74-69.57 mM, while they were in the range of 18.14-48.46 mM towards hCA II isoenzyme. K i values of the compounds 1-8 towards hCA I were in the range of 28.37 ± 6.63-70.58 ± 6.67 mM towards hCA I isoenzyme and they were in the range of 10.85 ± 2.14-37.96 ± 2.36 mM towards hCA II isoenzyme.

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Synthesis of Novel Substituted 1,3-diarylpropenone Derivatives and their In Vitro Cytotoxic Activity

Cited by 5 publications

References 0 publications

(E)-3-Methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone

(E)-3-Methyl-6-(3-oxo-3-(thiophen-2-yl)-1-propenyl)-2(3H)-benzothiazolone

New halogenated chalcones with cytotoxic and carbonic anhydrase inhibitory properties: 6‐(3‐Halogenated phenyl‐2‐propen‐1‐oyl)‐2(3H)‐benzoxazolones

Synthesis, cytotoxicities, and carbonic anhydrase inhibition potential of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones

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