Ultrasound assisted synthesis and cytotoxicity evaluation of known 2′,4′-dihydroxychalcone derivatives against cancer cell lines

Villena, Joan; Montenegro, Iván; Said, Bastián; Werner, Enrique; Flores, Susana; Madrid, Alejandro

doi:10.1016/j.fct.2021.111969

Cited by 7 publications

(3 citation statements)

References 41 publications

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“…In our study, the human cancer cell lines used were MCF-7 (breast adenocarcinoma); HT-29 (colorectal adenocarcinoma); PC-3 (prostate adenocarcinoma); and MCF-10 control cells (normal breast epithelium). For comparative purposes, the literature IC 50 values of daunorubicin and 5-fluorouracil (5-FU), measured in the same cell lines and under the same experimental conditions, were included [27][28][29]. Similarly, drimenol (1) was included for comparative purposes [28].…”

Section: Biological Evaluationmentioning

confidence: 99%

Cytotoxic Activity, Topoisomerase I Inhibition and In Silico Studies of New Sesquiterpene-aryl Ester Derivatives of (-) Drimenol

et al. 2023

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In this study, we aimed to evaluate two sets of sesquiterpene-aryl derivatives linked by an ester bond, their cytotoxic activities, and their capacity to activate caspases 3/7 and inhibit human topoisomerase I (TOP1). A total of 13 compounds were synthesized from the natural sesquiterpene (-)-drimenol and their cytotoxic activity was evaluated in vitro against three cancer cell lines: PC-3 (prostate cancer), HT-29 (colon cancer), MCF-7 (breast cancer), and an immortalized non-tumoral cell line (MCF-10). From the results, it was observed that 6a was the most promising compound due to its cytotoxic effect on three cancer cell lines and its selectivity, 6a was 100-fold more selective than 5-FU in MCF-7 and 20-fold in PC-3. It was observed that 6a also induced apoptosis by caspases 3/7 activity using a Capsase-Glo-3/7 assay kit and inhibited TOP1. A possible binding mode of 6a in a complex with TOP1-DNA was proposed by docking and molecular dynamics studies. In addition, 6a was predicted to have a good pharmacokinetic profile for oral administration. Therefore, through this study, it was demonstrated that the drimane scaffold should be considered in the search of new antitumoral agents.

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Section: Biological Evaluationmentioning

confidence: 99%

Cytotoxic Activity, Topoisomerase I Inhibition and In Silico Studies of New Sesquiterpene-aryl Ester Derivatives of (-) Drimenol

et al. 2023

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“…[68] Versatile chalcones have been recently synthesized using an ultrasound-aided approach. [69][70][71][72] In addition, this approach has been used for the stereoselective synthesis of a series of dihydro benzofuran chalcone derivative 6 at room temperature. In conclusion, the mentioned traditional and unconventional approaches have been established for constructing carbon−carbon bonds under moderate conditions with satisfactory yields, producing various beneficial chalcone derivatives that have potential importance in areas of synthetic and medicinal chemistry.…”

Section: Ultrasound-aided Approachmentioning

confidence: 99%

Recent Updates on Synthetic Strategies of Chalcone Scaffold and their Heterocyclic Derivatives

Amin

Shaykoon

Marzouk

et al. 2023

Journal of advanced Biomedical and Pharmaceutical Sciences

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Chalcones, α,β-unsaturated ketone linking two aromatic moieties gained noticeable attention in the medicinal chemistry area. Chalconescaffold construction has proceeded via verified chemical synthetic strategies, including condensation, coupling, olefination, acylation, reductive annulation, one-pot, and Fries' rearrangement methods. Specific approaches have assisted chalcone combinations using microwave radiation and ultrasound waves to enhance synthetic conditions and amplify yields. Recently, chalcones have been investigated extensively as core structures in potent bioactive hybrids such as anticancer, antimicrobial, and others. In addition, chalcones serve as parent structures for synthesizing several bioactive heterocyclic derivatives comprising five-membered and six-membered rings. This review will discuss recent applications of chalcones' synthetic strategies, physical and chemical characters, biological activities, and chemical derivatization.

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“…The reaction mixture was irradiated in a water bath by an ultrasonic cleaner. The ultrasonic system allowed to reduce reaction time, improving the overall alkylation yields ( Villena et al, 2021 ). Several aryl/indolyl substituted 4,5-dihydro-1 H -pyrazole derivatives were synthesized by Kannan and co-workers.…”

Section: 1 Ultrasound Chemistrymentioning

confidence: 99%

The green chemistry of chalcones: Valuable sources of privileged core structures for drug discovery

Marotta

Rossi²,

Ibba³

et al. 2022

Front. Chem.

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The sustainable use of resources is essential in all production areas, including pharmaceuticals. However, the aspect of sustainability needs to be taken into consideration not only in the production phase, but during the whole medicinal chemistry drug discovery trajectory. The continuous progress in the fields of green chemistry and the use of artificial intelligence are contributing to the speed and effectiveness of a more sustainable drug discovery pipeline. In this light, here we review the most recent sustainable and green synthetic approaches used for the preparation and derivatization of chalcones, an important class of privileged structures and building blocks used for the preparation of new biologically active compounds with a broad spectrum of potential therapeutic applications. The literature here reported has been retrieved from the SciFinder database using the term “chalcone” as a keyword and filtering the results applying the concept: “green chemistry”, and from the Reaxys database using the keywords “chalcone” and “green”. For both databases the time-frame was 2017–2022. References were manually selected based on relevance.

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Ultrasound assisted synthesis and cytotoxicity evaluation of known 2′,4′-dihydroxychalcone derivatives against cancer cell lines

Cited by 7 publications

References 41 publications

Cytotoxic Activity, Topoisomerase I Inhibition and In Silico Studies of New Sesquiterpene-aryl Ester Derivatives of (-) Drimenol

Cytotoxic Activity, Topoisomerase I Inhibition and In Silico Studies of New Sesquiterpene-aryl Ester Derivatives of (-) Drimenol

Recent Updates on Synthetic Strategies of Chalcone Scaffold and their Heterocyclic Derivatives

The green chemistry of chalcones: Valuable sources of privileged core structures for drug discovery

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