Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones

Teixeira, Róbson Ricardo; Barbosa, Luiz C. A.; Maltha, Célia R. A.; Rocha, Marcelo Eça; Bezerra, Daniel P.; Costa-Lotuf, Letícia Veras; Pessoa, Cláudia; Moraes, Manoel Odoríco de

doi:10.3390/12051101

Cited by 40 publications

(24 citation statements)

References 41 publications

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“…MTT test is one of the most important pre-screening methods to investigate cell proliferation and anticancer activity of natural products and synthetic materials in the search for new drugs (Jamalian et al, 2011;Mosmann, 1983;Teixeira et al, 2007). In this context, MTT test's results of the complexes, solvent and starting components were assessed.…”

Section: Mtt Assaymentioning

confidence: 99%

Determination of Cytotoxicity of Zinc 2-Bromobenzoate with Nicotinamide and N,N'-Diethylnicotinamide Complexes

Akbaba

2020

Caucasian Journal of Science

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Benzoic acid and its derivatives and their metal complexes, which have antimicrobial, anticancer, antituberculosis and antioxidant properties, are biologically active molecules. Although there are many studies on the biological activity of these compounds, studies on the determination of their toxicity are limited. In the presented study, the cytotoxic properties of the previously synthesized diaquabis(2-bromobenzoato-κO)bis(nicotinamide-κN1)zinc(II) (ZnBrBANA) and diaquabis(2-bromobenzoato-κO)bis(N,N'-diethylnicotinamide-κN1)zinc(II) (ZnBrBADENA) complexes were investigated. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay, a colorimetric method, was used to determine the cytotoxicity of complexes on human peripheral lymphocyte cells. Besides, cytotoxicity of dimethylsulfoxide (DMSO) which is crystal solvent and 2-bromobenzoic acid (BrBA), nicotinamide (NA), and N,N'-dietyhlnicotinamide (DENA) which are starting compounds of the complexes was also evaluated. According to the results of MTT method, It has been determined that both complexes and starting components except BrBA cause cytotoxicity on lymphocyte cells at the concentration range of 62.5-500 ppm. In addition, it was determined that the BrBA and DMSO at the same concentration range do not show any cytotoxic effect on lymphocyte cells. It was observed that the synthesized complexes were more toxic at each concentration than the starting components. Therefore, the toxic effects of the complexes used as drug active ingredients should be followed up with new studies.

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Section: Mtt Assaymentioning

confidence: 99%

Determination of Cytotoxicity of Zinc 2-Bromobenzoate with Nicotinamide and N,N'-Diethylnicotinamide Complexes

Akbaba

2020

Caucasian Journal of Science

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“…[ 30 ] We have also been involved in the search and development of new compounds that can be possible alternatives for cancer and leishmaniasis treatment. [ 31–46 ]…”

Section: Introductionmentioning

confidence: 99%

Leishmanicidal and cytotoxic activities and 4D‐QSAR of 2‐arylidene indan‐1,3‐diones

Souza

Costa

Aguiar

et al. 2021

Archiv der Pharmazie

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The indan‐1,3‐dione and its derivatives are important building blocks in organic synthesis and present important biological activities. Herein, the leishmanicidal and cytotoxicity evaluation of 16 2‐arylidene indan‐1,3‐diones is described. The compounds were evaluated against the leukemia cell lines HL60 and Nalm6, and the most effective ones were 2‐(4‐nitrobenzylidene)‐1H‐indene‐1,3(2H)‐dione (4) and 4‐[(1,3‐dioxo‐1H‐inden‐2(3H)‐ylidene)methyl]benzonitrile (10), presenting IC50 values of around 30 µmol/L against Nalm6. The leishmanicidal activity was assessed on Leishmania amazonensis, with derivative 4 (IC50 = 16.6 µmol/L) being the most active. A four‐dimensional quantitative structure–activity analysis (4D‐QSAR) was applied to the indandione derivatives, through partial least‐squares regression. The statistics presented by the regression models built with the selected field descriptors of Coulomb (C) and Lennard‐Jones (L) nature, considering the activities against L. amazonensis, HL60, and Nalm6 leukemia cells, were, respectively, R2 = 0.88, 0.92, and 0.98; Q2 = 0.83, 0.88, and 0.97. The presence of positive Coulomb descriptors near the carbonyl groups indicates that these polar groups are related to the activities. Besides, the presence of positive Lennard‐Jones descriptors close to substituents R3 or R1 indicates that bulky nonpolar substituents in these positions tend to increase the activities. This study provides useful insights into the mode of action of indandione derivatives for each biological activity involved.

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“…The butenolide subunit is an appealing heterocyclic system that can be found in a vast array of pharmacologically active natural and nonnatural products . For example, the association of the butenolide core with a benzyl and arylvinylidene group is of particular interest because of the phytotoxic, cytotoxic, and marine antifouling activities of such molecules.…”

Section: Introductionmentioning

confidence: 99%

Straightforward and Regioselective Access to Unsaturated α‐Benzyl Butyrolactones

et al. 2017

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The efficient preparation of various substituted α‐benzyl unsaturated butyrolactones is described. The palladium‐mediated C–C bond formation that uses α‐bromomethylbutenolide and boron derivatives as coupling partners accounts for the key step of this synthetic approach. Our strategy exclusively affords the endocyclic adduct and represents an alternative to Heck‐type reactions. The synthesis and characterization of two nostoclide analogues has also been reported.

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Synthesis and Cytotoxic Activity of Some 3-Benzyl-5-Arylidenefuran-2(5H)-ones

Cited by 40 publications

References 41 publications

Determination of Cytotoxicity of Zinc 2-Bromobenzoate with Nicotinamide and N,N'-Diethylnicotinamide Complexes

Determination of Cytotoxicity of Zinc 2-Bromobenzoate with Nicotinamide and N,N'-Diethylnicotinamide Complexes

Leishmanicidal and cytotoxic activities and 4D‐QSAR of 2‐arylidene indan‐1,3‐diones

Straightforward and Regioselective Access to Unsaturated α‐Benzyl Butyrolactones

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