Synthesis and biological evaluation of 3-functionalized 2-phenyl- and 2-alkylbenzo[b]furans as antiproliferative agents against human melanoma cell line

Kwiecień, H.; Perużyńska, Magdalena; Stachowicz, Karolina; Piotrowska, Katarzyna; Bujak, Joanna; Kopytko, Patrycja; Droździk, Marek

doi:10.1016/j.bioorg.2019.102930

Cited by 10 publications

(4 citation statements)

References 37 publications

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“…The routes for the synthesis of 2-arylbenzofuran derivatives are shown in Scheme 2 and the final products are listed in Table 1 . The synthesis method of 2-arylbenzofuran compound is based on the Droździk and co-workers’ method and slightly optimized 30 . O -Alkylation of the substituted 2-hydroxybenzaldehyde with methyl α-bromophenylacetate in the presence of potassium carbonate in dimethylformamide gave the corresponding methyl 2–(2-formylphenoxy)-2 -phenylacetates in high yields.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of 2-arylbenzofuran derivatives as potential anti-Alzheimer’s disease agents

Yun

Miao

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Alzheimer's disease (AD) is a type of progressive dementia caused by degeneration of the nervous system. A single target drug usually does not work well. Therefore, multi-target drugs are designed and developed so that one drug can specifically bind to multiple targets to ensure clinical effectiveness and reduce toxicity. We synthesised a series of 2-arylbenzofuran derivatives and evaluated their in vitro activities. 2-Arylbenzofuran compounds have good dual cholinesterase inhibitory activity and b-secretase inhibitory activity. The IC 50 value of compound 20 against acetylcholinesterase inhibition (0.086 ± 0.01 mmolÁL À1 ) is similar to donepezil (0.085 ± 0.01 mmolÁL À1 ) and is better than baicalein (0.404 ± 0.04 mmolÁL À1 ). And most of the compounds have good BACE1 inhibitory activity, of which 3 compounds (8, 19 and 20) show better activity than baicalein (0.087 ± 0.03 mmolÁL À1 ). According to experimental results, 2-arylbenzofuran compounds provide an idea for drug design to develop prevention and treatment for AD.

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Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of 2-arylbenzofuran derivatives as potential anti-Alzheimer’s disease agents

Yun

Miao

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Furan and its derivative may act on different targets including inhibition of tubulin polymerization leading to disruption of mitotic spindle formation and activated AKT/MAPK pathways which arrest cell cycle (G2/M phase), apoptosis and proliferation of cell [81–82] …”

Section: Imidazole Hybridizes With Other Anticancer Pharmacophoresmentioning

confidence: 99%

Hybridization of Imidazole with Various Heterocycles in Targeting Cancer: A Decade's Work

Teli¹,

Chawla²

2021

ChemistrySelect

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Cancer is the world‘s biggest global health concern. The prevalence and mortality rates of cancer remain high despite significant progress in cancer therapy. The search for more effective, as well as less toxic treatment methods for cancer, is at the focus of current studies. Approximately 24.6 million people are suffering from cancer across the world as per the world health organization (WHO). In the year 2020, approximately 10 million deaths were reported due to cancer which has emerged as the second leading cause of mortality across the globe. Anticancer medicines have played a pivotal role in the medication of different types of cancers; however, they are associated with several side effects and relevance of drug resistance which evoke an immediate need for designing of new anticancer agents with multitargeted effect. Imidazole is a heterocyclic compound privileged with considerable anticancer activities and some imidazole derivatives have already got approval to treat cancer. Many hybrid molecules are available that play an important role in the treatment of cancer like chalcone, pyrazole, purine, triazine etc., and their pharmacophore provide the anticancer drug with low drug resistance and high efficacy, with low chances of toxicity and side effects. This review provides various approaches for the drug development of new safe and efficient antitumor agents imidazole hybrids with other heterocyclic moieties. An attempt has been made to advancement of the anticancer potential of the derivatives and hybrids of imidazole having intact or condensed imidazole moiety in the last decade along with the structure‐activity relationship studies, and mechanism of action.

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“…Furans are convenient intermediates in the synthesis of drugs, such as furosemide 1 , a popular diuretic, and cefuroxime 2 , a penicillin derivative [ 1 ] ( Figure 1 ). Furan compounds are used as anticancer drugs [ 2 , 3 , 4 , 5 ] and serve as a framework for the development of new HIV inhibitors [ 6 , 7 , 8 ], antioxidant [ 9 ] and antibacterial [ 10 , 11 , 12 ] drugs, and agents for the prevention and treatment of diseases associated with estrogen deficiency [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis, E-/Z-Equilibrium in Solution of 3-Hetarylaminomethylidenefuran-2(3H)-ones and the Way to Selective Synthesis of the E-Enamines

2023

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We describe a method to synthesize a new class of hetarylaminomethylidene derivatives of furan-2(3H)-ones. The method uses 5-(4-chlorophenyl)furan-2(3H)-one, triethyl orthoformate, and heterocyclic amines with different ring sizes and heteroatoms under refluxing in absolute isopropyl alcohol. The obtained enamines exist in an equilibrium of E- and Z-isomers, whose configurations relative to the double exocyclic C=C bond were confirmed with a set of NMR spectroscopy data. The E-/Z-equilibrium of the synthesized compounds is affected by the configuration of the intermediate, the volume of its substituents, the site of enolate attack, the presence of intramolecular interactions of amino components, the time of the transformation, the order of mixing of the initial reagents, and the use of polar solvents in the NMR experiment. The advantages of the method are that the reaction time is short, the product yield is high, and product purification is easy.

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Synthesis and biological evaluation of 3-functionalized 2-phenyl- and 2-alkylbenzo[b]furans as antiproliferative agents against human melanoma cell line

Cited by 10 publications

References 37 publications

Synthesis and biological evaluation of 2-arylbenzofuran derivatives as potential anti-Alzheimer’s disease agents

Synthesis and biological evaluation of 2-arylbenzofuran derivatives as potential anti-Alzheimer’s disease agents

Hybridization of Imidazole with Various Heterocycles in Targeting Cancer: A Decade's Work

One-Pot Synthesis, E-/Z-Equilibrium in Solution of 3-Hetarylaminomethylidenefuran-2(3H)-ones and the Way to Selective Synthesis of the E-Enamines

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