Synthesis and evaluation of the cytotoxic activity of Furanaphthoquinones tethered to 1H-1,2,3-triazoles in Caco-2, Calu-3, MDA-MB231 cells

Costa, Dora C. S.; Almeida, Gabriella Silva de; Rabelo, Vitor Won‐Held; Cabral, Lúcio Mendes; Sathler, P.C; Abreu, Paula Alvarez; Ferreira, Vı́tor F.; Silva, Luiz Cláudio Rodrigues Pereira da; Silva, Fernando de Carvalho da

doi:10.1016/j.ejmech.2018.07.018

Cited by 25 publications

(7 citation statements)

References 35 publications

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“…Another hybrid, 1,2,3-triazole-related naphthoquinone, inhibited cancer cells such as Caco-2, Calu-3, and MDA-MB231 cells, as well as normal Vero cells. 80 Among them, compound 42 ( Fig. 6) with a cell viability of 23.92% on Caco-2 cells, showed 6-fold higher selectivity on Caco-2 than Vero cells (selectivity index [SI] = 6.25), confirming the potential of this derivative as a drug-like candidate.…”

Section: Diverse 123-triazole-containing Heterocyclic Hybridsmentioning

confidence: 80%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

534

282

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A B S T R A C TThe 1,2,3-triazole ring is a major pharmacophore system among nitrogen-containing heterocycles. These fivemembered heterocyclic motifs with three nitrogen heteroatoms can be prepared easily using 'click' chemistry with copper-or ruthenium-catalysed azide-alkyne cycloaddition reactions. Recently, the 'linker' property of 1,2,3-triazoles was demonstrated, and a novel class of 1,2,3-triazole-containing hybrids and conjugates was synthesised and evaluated as lead compounds for diverse biological targets. These lead compounds have been demonstrated as anticancer, antimicrobial, anti-tubercular, antiviral, antidiabetic, antimalarial, anti-leishmanial, and neuroprotective agents. The present review summarises advances in lead compounds of 1,2,3-triazolecontaining hybrids, conjugates, and their related heterocycles in medicinal chemistry published in 2018. This review will be useful to scientists in research fields of organic synthesis, medicinal chemistry, phytochemistry, and pharmacology. Chemistry: synthesis and properties of the 1,2,3-triazolesThe general synthetic route of 1,2,3-triazoles using click chemistry is described in Scheme 1A. The most popular route to 1,2,3-triazoles is Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition, which is the https://doi.

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Section: Diverse 123-triazole-containing Heterocyclic Hybridsmentioning

confidence: 80%

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Bozorov

Zhao

Aisa

2019

Bioorganic & Medicinal Chemistry

534

282

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“…Naphthoquinones present a chemical structure of naphthalene with two ketone groups at position C-1 and C-2 (1,2-naphthoquinones) or C-1 and C-4 (1,4-naphthoquinones) [ 9 ]. The considerable interest in these compounds is based on their pharmacological activities, especially as antimicrobial [ [8] , [9] , [10] , [11] ] and antitumor agents [ [12] , [13] , [14] , [15] ]. Most recently, 1,4-naphthoquinones, such as menadione (vitamin K3), have aroused a lot of interest due to relevant anticancer activity [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Anti-tubercular profile of new selenium-menadione conjugates against Mycobacterium tuberculosis H37Rv (ATCC 27294) strain and multidrug-resistant clinical isolates

Ribeiro

Marins

Leo

et al. 2021

European Journal of Medicinal Chemistry

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Tuberculosis (TB) is one of the most fatal diseases and is responsible for the infection of millions of people around the world. Most recently, scientific frontiers have been engaged to develop new drugs that can overcome drug-resistant TB. Following this direction, using a designed scaffold based on the combination of two separate pharmacophoric groups, a series of menadione-derived selenoesters was developed with good yields. All products were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv and attractive results were observed, especially for the compounds 8a , 8c and 8f (MICs 2.1, 8.0 and 8.1 μM, respectively). In addition, 8a , 8c and 8f demonstrated potent in vitro activity against multidrug-resistant clinical isolates (CDCT-16 and CDCT-27) with promising MIC values ranging from 0.8 to 3.1 μM. Importantly, compounds 8a and 8c were found to be non-toxic against the Vero cell line. The SI value of 8a (>23.8) was found to be comparable to that of isoniazid (>22.7), which suggests the possibility of carrying out advanced studies on this derivative. Therefore, these menadione-derived selenoesters obtained as hybrid compounds represent promising new anti-tubercular agents to overcome TB multidrug resistance.

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“… Lapachone or nor-lapachone–substituted 1,2,3-triazole hybrids as reported by Bahia et al [ 64 ], and by Costa et al [ 65 ]. …”

Section: Figurementioning

confidence: 74%

“…More recently, Costa et al [ 65 ] reported another series of NQ-hybrids presenting the 1,2,3-triazole scaffold functionalized by an aryl moiety with different substituents. The synthesis involved the reaction between 2-hydroxy-1,4-naphthoquinone and vinyl 1,2,3-triazoles presenting the suitable aryl substituents, with cerium (IV) ammonium nitrate as the oxidizing agent.…”

Section: Design Synthesis and Biological Evaluation Of Antitumor Hybridsmentioning

confidence: 99%

Hybrid Molecules Containing Naphthoquinone and Quinolinedione Scaffolds as Antineoplastic Agents

et al. 2022

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In recent decades, molecular hybridization has proven to be an efficient tool for obtaining new synthetic molecules to treat different diseases. Based on the core idea of covalently combining at least two pharmacophore fragments present in different drugs and/or bioactive molecules, the new hybrids have shown advantages when compared with the compounds of origin. Hybridization could be successfully applied to anticancer drug discovery, where efforts are underway to develop novel therapeutics which are safer and more effective than those currently in use. Molecules presenting naphthoquinone moieties are involved in redox processes and in other molecular mechanisms affecting cancer cells. Naphthoquinones have been shown to inhibit cancer cell growth and are considered privileged structures and useful templates in the design of hybrids. The present work aims at summarizing the current knowledge on antitumor hybrids built using 1,4- and 1,2-naphthoquinone (present in natural compounds as lawsone, napabucasin, plumbagin, lapachol, α-lapachone, and β -lapachone), and the related quinolone- and isoquinolinedione scaffolds reported in the literature up to 2021. In detail, the design and synthetic approaches adopted to produce the reported compounds are highlighted, the structural fragments considered in hybridization and their biological activities are described, and the structure–activity relationships and the computational analyses applied are underlined.

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Synthesis and evaluation of the cytotoxic activity of Furanaphthoquinones tethered to 1H-1,2,3-triazoles in Caco-2, Calu-3, MDA-MB231 cells

Cited by 25 publications

References 35 publications

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview

Anti-tubercular profile of new selenium-menadione conjugates against Mycobacterium tuberculosis H37Rv (ATCC 27294) strain and multidrug-resistant clinical isolates

Hybrid Molecules Containing Naphthoquinone and Quinolinedione Scaffolds as Antineoplastic Agents

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