Green synthesis of ferrocenyl chalcones against triple negative breast cancer

Tang, Wenqiang; Gao, Yankun; Tong, Hongjuan; Xu, Xiaona; Zhu, Zhoujing; Liu, Bin

doi:10.1016/j.jorganchem.2023.122640

Cited by 3 publications

(4 citation statements)

References 34 publications

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“…Compounds 1 (with an unsubstituted phenyl nucleus) and 5 (with a nitro group in the m-position of the phenyl nucleus) show moderate activity (22.5 and 33.1%, respectively), while compound 4 with a methoxy group in the o-position has weak antioxidant activity (5.1%). (1)(2)(3)(4)(5) using the ABTS method.…”

Section: Resultsmentioning

confidence: 99%

“…Concerning nematicidal activity, (2E)-1-(3-bromophenyl)-3-ferrocenyl-prop-2-en-1-one was the most potent [2]. Results of in vitro antiproliferative activity and SAR study of various ferrocenyl chalcones showed that the aldehyde unit of ferrocenyl chalcones containing halogens or dimethyl substituents was the most effective structural moiety against MDA-MB-231 cells [5]. Smit and coworkers demonstrated that aminoferrocenyl-chalcone amide containing a piperazinyl linker, possessed increased activity against three cancer cell lines: TK-10 (human kidney renal cell adenocarcinoma, UACC-62 (melanotic melanoma), and MCF-7(breast cancer), compared to the reference drug, parthenolide [6].…”

Section: Introductionmentioning

confidence: 99%

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In vitro antioxidant activity evaluation of ferrocenyl chalcones

Lazić,

Matović,

Lađarević

et al. 2023

Proceedings of the 36th International Congress on Process Engineering

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Ferrocene derivatives are known as antioxidants, antiparasitic, antitumor, antiviral, antibacterial and antifungal agents. In addition to applications in medicinal chemistry and drug design, ferrocene derivatives are of exceptional importance in synthetic organic chemistry, especially in catalytic asymmetric transformations. They are also used in electrochemistry and polymer chemistry, as additives in fuels, as chemosensors in agrochemistry and biosensors of glucose and active components in molecular electronics. To design new antioxidant agents, five ferrocenyl chalcones were synthesized, and fully characterized by melting points, FT-IR, 1H and 13C NMR spectroscopic methods. The synthesized chalcones differ in the nature and the position of the substituent attached to the phenyl group in position 1 of the linear unsaturated carbonyl system. The potential antioxidant activity of the synthesized compounds was evaluated using the ABTS (2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) method and IC50 values of the most effective compounds were further determined.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

In vitro antioxidant activity evaluation of ferrocenyl chalcones

Lazić,

Matović,

Lađarević

et al. 2023

Proceedings of the 36th International Congress on Process Engineering

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“…showed potent antiproliferative activity against MDA-MB-231 cancer cells, whereas hybrid 68b (IC 50 : 6.4 and 8.8 µM) possessed promising activity against MCF-7 and MDA-MB-231 breast cancer cell lines, and the antiproliferative activity was superior to that of tamoxifen (IC 50 : 15.6 and 17.4 µM). [103] In addition, hybrids 68a,b (IC 50 : >100 µM) were nontoxic toward normal MCF-10A breast cells, and SI values were >11. [104,105] A vast majority of chalcone-sulfonamide hybrids 70 (IC 50 :…”

Section: Miscellaneous Chalcone Hybridsmentioning

confidence: 98%

“…Chalcone‐ferrocene hybrid 68a (IC 50 : 2.4 µM, MTT assay) showed potent antiproliferative activity against MDA‐MB‐231 cancer cells, whereas hybrid 68b (IC 50 : 6.4 and 8.8 µM) possessed promising activity against MCF‐7 and MDA‐MB‐231 breast cancer cell lines, and the antiproliferative activity was superior to that of tamoxifen (IC 50 : 15.6 and 17.4 µM). [ 103 ] In addition, hybrids 68a,b (IC 50 : >100 µM) were nontoxic toward normal MCF‐10A breast cells, and SI values were >11.3, revealing their excellent selectivity profiles. Mechanistically, hybrid 68a could exert antiproliferative activity through inhibition of cyclooxygenase‐2 (COX‐2, IC 50 : 2.4 µM).…”

Section: Miscellaneous Chalcone Hybridsmentioning

confidence: 99%

Current scenario of chalcone hybrids with antibreast cancer therapeutic applications

Wang,

Zhu,

Zhang

et al. 2024

Archiv der Pharmazie

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Breast cancer, an epithelial malignant tumor that occurs in the terminal ducts of the breast, is the most common female malignancy. Currently, approximately 70%–80% of breast cancer with early‐stage, nonmetastatic disorder is curable, but the emergency of drug resistance often leads to treatment failure. Moreover, advanced breast cancer with distant organ metastases is incurable with the available therapeutics, creating an urgent demand to explore novel antibreast cancer agents. Chalcones, the precursors for flavonoids and isoflavonoids, exhibit promising activity against various breast cancer hallmarks, inclusive of proliferation, angiogenesis, invasion, metastasis, inflammation, stemness, and regulation of cancer epigenetics, representing useful scaffolds for the discovery of novel antibreast cancer chemotherapeutic candidates. In particular, chalcone hybrids could act on two or more different biological targets simultaneously with more efficacy, lower toxicity, and less susceptibility to resistance. Accordingly, there is a huge scope for application of chalcone hybrids to tackle the present difficulties in breast cancer therapy. This review outlines the chalcone hybrids with antibreast cancer potential developed from 2018. The structure–activity relationships as well as mechanisms of action are also discussed to shed light on the development of more effective and multitargeted chalcone candidates.

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