Design, synthesis and anticancer activity of benzofuran derivatives targeting VEGFR-2 tyrosine kinase

Abdelhafez, Omaima M.; Amin, Kamelia M.; Ali, Hamed I.; Abdalla, Mohamed M.; Ahmed, Eman Y.

doi:10.1039/c4ra00943f

Cited by 48 publications

(24 citation statements)

References 33 publications

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“…Today, a large number of benzofuran-based drugs are available on the market, including examples such as Methoxsalen that is used against psoriasis and eczema, the antiarrhythmic medications Amiodarone and Dronedarone, as well as the antidepressant Vilazodone (Figure 1) [1][2][3][4]. Furthermore, other benzofuran derivatives have been shown to display a wide range of antimicrobial and anticancer properties [1][2][3][4][5][6][7]. Given the vast number of applications of benzofuran-based drugs in today's medicine, there exists considerable interest for novel synthetic methodologies that can grant expedient access to new kinds of benzofuran derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry

et al. 2020

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Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C–H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C–H arylation reactions, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a one-pot, two-step transamidation procedure, which proceeded via the intermediate N-acyl-Boc-carbamates. Given the high efficiency and modularity of this synthetic strategy, it constitutes a very attractive method for generating structurally diverse collections of benzofuran derivatives for small molecule screening campaigns.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry

et al. 2020

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“…[8] Benzbromarone 6 and Ramelteon 7 are benzofuran ring containing drug molecules mainly availed in the medication of gout and treatment of delayed sleep phase syndrome. [9,10] Also, several synthetic benzofurans have been reported to exhibit diverse bio-activities like anticancer, [11] antiviral, [12] antivasoconstriction, [13] 5-lipoxygenase inhibition, [14] antiinflammation, [15] and antioxidant activities. [16] In literature plethora of synthetic methods are documented to prepare 2-arylbenzofurans.…”

Section: Introductionmentioning

confidence: 99%

Ultrasonic‐Assisted Hypervalent Iodine‐Catalyzed Cyclization of (E)‐2‐Hydroxystilbenes to Benzofurans Using Iodobenzene as Pre‐catalyst

Mangaonkar¹,

Shetgaonkar²,

Vernekar

et al. 2020

ChemistrySelect

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A rapid, and metal‐free approach for the synthesis of functionalized benzofurans 10 is illustrated by PhI 9 catalyzed cyclization of 2‐hydroxystilbenes 8. The 2‐hydroxystilbenes 8 were cyclized using 10 mol % PhI as a precatalyst, 2.0 equiv. of m‐CPBA as an oxidant and 2.4 equiv. of TFA as an additive at room temperature under ultrasonic irradiation condition. The functionalized benzofurans 10 were gained in good to excellent yields with shorter reaction times.

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“…Benzofuran and its analogues are important core structures for drug discovery, showing excellent pharmacological activity like antiviral [13], anticancer [14], anti-inflammatory [15], antihyperlipidemic [16], anti-Alzheimer’s [17], anticonvulsant [18], antitubercular [19], CNS regulatory [20], analgesic [21], enzyme inhibition [22,23], antipyretic activities [24].…”

Section: Introductionmentioning

confidence: 99%

Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase

et al. 2019

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Inhibition of α-amylase and α-glucosidase by specified synthetic compounds during the digestion of starch helps control post-prandial hyperglycemia and could represent a potential therapy for type II diabetes mellitus. A new series of spiroheterocyclic compounds bearing oxindole/benzofuran/pyrrolidine/thiazolidine motifs were synthesized via a 1,3-dipolar cyclo-addition reaction approach. The specific compounds were obtained by reactions of chalcones having a benzo[b]furan scaffold (compounds 2a–f), with a substituted isatin (compounds 3a–c) and heterocyclic amino acids (compounds 4a,b). The target spiroindolone analogues 5a–r were evaluated for their potential inhibitory activities against the enzymes α-amylase and α-glucosidase. Preliminary results indicated that some of the target compounds exhibit promising α-amylase and α-glucosidase inhibitory activity. Among the tested spiroindolone analogues, the cycloadduct 5r was found to be the most active (IC50 = 22.61 ± 0.54 μM and 14.05 ± 1.03 μM) as α-amylase and α-glucosidase inhibitors, with selectivity indexes of 0.62 and 1.60, respectively. Docking studies were carried out to confirm the binding interaction between the enzyme active site and the spiroindolone analogues.

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Design, synthesis and anticancer activity of benzofuran derivatives targeting VEGFR-2 tyrosine kinase

Cited by 48 publications

References 33 publications

Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry

Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry

Ultrasonic‐Assisted Hypervalent Iodine‐Catalyzed Cyclization of (E)‐2‐Hydroxystilbenes to Benzofurans Using Iodobenzene as Pre‐catalyst

Spiroindolone Analogues as Potential Hypoglycemic with Dual Inhibitory Activity on α-Amylase and α-Glucosidase

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