Design, synthesis, characterization, and anticancer activity of a novel series of O-substituted chalcone derivatives

Ngameni, Bathélémy; Cedric, Kamdoum; Mbaveng, Armelle T.; Erdoğan, Musa; Simo, Ingrid Konga; Kuete, Victor; Daştan, Arif

doi:10.1016/j.bmcl.2021.127827

Cited by 28 publications

(12 citation statements)

References 50 publications

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“…Chalcones (1,3-diaryl-2-proper-1-ones) are naturally occurring precursors of flavonoids, and these compounds have broad pharmacological activities including anti-cancer, antifungal, anti-inflammatory, and antioxidative activity [ 97 , 115 , 116 , 117 , 118 ]. A novel series of imidazole-chalcone derivatives were developed, synthesized, and evaluated as tubulin inhibitors.…”

Section: Chalcone Analogsmentioning

confidence: 99%

Recent Advances of Tubulin Inhibitors Targeting the Colchicine Binding Site for Cancer Therapy

Hawash

2022

Biomolecules

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Cancer accounts for numerous deaths each year, and it is one of the most common causes of death worldwide, despite many breakthroughs in the discovery of novel anticancer candidates. Each new year the FDA approves the use of new drugs for cancer treatments. In the last years, the biological targets of anticancer agents have started to be clearer and one of these main targets is tubulin protein; this protein plays an essential role in cell division, as well as in intracellular transportation. The inhibition of microtubule formation by targeting tubulin protein induces cell death by apoptosis. In the last years, numerous novel structures were designed and synthesized to target tubulin, and this can be achieved by inhibiting the polymerization or depolymerization of the microtubules. In this review article, recent novel compounds that have antiproliferation activities against a panel of cancer cell lines that target tubulin are explored in detail. This review article emphasizes the recent developments of tubulin inhibitors, with insights into their antiproliferative and anti-tubulin activities. A full literature review shows that tubulin inhibitors are associated with properties in the inhibition of cancer cell line viability, inducing apoptosis, and good binding interaction with the colchicine binding site of tubulin. Furthermore, some drugs, such as cabazitaxel and fosbretabulin, have been approved by FDA in the last three years as tubulin inhibitors. The design and development of efficient tubulin inhibitors is progressively becoming a credible solution in treating many species of cancers.

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Section: Chalcone Analogsmentioning

confidence: 99%

Recent Advances of Tubulin Inhibitors Targeting the Colchicine Binding Site for Cancer Therapy

Hawash

2022

Biomolecules

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“… Homocyclic chalcones with anti-breast-cancer activity [ 170 , 171 , 172 , 173 , 174 , 175 , 176 , 177 , 178 , 179 , 180 , 181 , 182 , 183 ]. …”

Section: Figures Schemes and Tablesmentioning

confidence: 99%

Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

et al. 2022

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Chalcones are a class of privileged scaffolds with high medicinal significance due to the presence of an α,β-unsaturated ketone functionality. Numerous functional modifications of chalcones have been reported, along with their pharmacological behavior. The present review aims to summarize the structures from natural sources, synthesis methods, biological characteristics against infectious and non-infectious diseases, and uses of chalcones over the past decade, and their structure–activity relationship studies are detailed in depth. This critical review provides guidelines for the future design and synthesis of various chalcones. In addition, this could be highly supportive for medicinal chemists to develop more promising candidates for various infectious and non-infectious diseases.

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“…Chalcone and its derivatives ( Table 1 ) exhibit significant antioxidant, anti-inflammatory and anticancer activities [ 165 , 166 , 167 , 168 ]. Their ability to activate the NRF2 signaling pathway has been attributed to the presence of an α,β-unsaturated carbonyl moiety [ 7 ].…”

Section: αβ-Unsaturated Carbonylsmentioning

confidence: 99%

An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects

Egbujor

Buttari²,

Profumo³

et al. 2022

IJMS

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The surge of scientific interest in the discovery of Nuclear Factor Erythroid 2 (NFE2)-Related Factor 2 (NRF2)-activating molecules underscores the importance of NRF2 as a therapeutic target especially for oxidative stress. The chemical reactivity and biological activities of several bioactive compounds have been linked to the presence of α,β-unsaturated structural systems. The α,β-unsaturated carbonyl, sulfonyl and sulfinyl functional groups are reportedly the major α,β-unsaturated moieties involved in the activation of the NRF2 signaling pathway. The carbonyl, sulfonyl and sulfinyl groups are generally electron-withdrawing groups, and the presence of the α,β-unsaturated structure qualifies them as suitable electrophiles for Michael addition reaction with nucleophilic thiols of cysteine residues within the proximal negative regulator of NRF2, Kelch-like ECH-associated protein 1 (KEAP1). The physicochemical property such as good lipophilicity of these moieties is also an advantage because it ensures solubility and membrane permeability required for the activation of the cytosolic NRF2/KEAP1 system. This review provides an overview of the reaction mechanism of α,β-unsaturated moiety-bearing compounds with the NRF2/KEAP1 complex, their pharmacological properties, structural activity-relationship and their effect on antioxidant and anti-inflammatory responses. As the first of its kind, this review article offers collective and comprehensive information on NRF2-activators containing α,β-unsaturated moiety with the aim of broadening their therapeutic prospects in a wide range of oxidative stress-related diseases.

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Design, synthesis, characterization, and anticancer activity of a novel series of O-substituted chalcone derivatives

Cited by 28 publications

References 50 publications

Recent Advances of Tubulin Inhibitors Targeting the Colchicine Binding Site for Cancer Therapy

Recent Advances of Tubulin Inhibitors Targeting the Colchicine Binding Site for Cancer Therapy

Chalcone: A Promising Bioactive Scaffold in Medicinal Chemistry

An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects

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