Synthesis of New Derivatives of Benzofuran as Potential Anticancer Agents

Napiórkowska, Mariola; Cieślak, Marcin; Kaźmierczak-Barańska, Julia; Królewska-Golińska, Karolina; Nawrot, Barbara

doi:10.3390/molecules24081529

Cited by 30 publications

(17 citation statements)

References 23 publications

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“…The interest in heterocyclic compounds due to their special medicinal properties. The FTIR studies, 1 H NMR and elemental analysis indicated the formation of benzoforan and its derivatives.…”

Section: Discussionmentioning

confidence: 99%

“…Benzofuran derivatives are a major group of biologically active heterocycles which are usually important constituents of plant extracts used in medicinal chemistry for their various biological activities. [1][2][3] Due to their diverse activities, much attention has been paid to synthetic strategies to access these systems, and a number of methods have been developed. 4 Pyrolysis of 2-pyrone at 900-1000 o C in a stream of nitrogen leads to ring contraction into furan.…”

Section: Introductionmentioning

confidence: 99%

“…of the compound was checked by TLC. IR spectra were recorded on a Perkin Elmer 157 spectrometer 1. H NMR spectra were recorded in acetone / CCl 4 on a Bruker WM 400 MHz spectrometer using TMS as an internal reference.…”

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confidence: 99%

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Fast Synthesis of Benzofurans from Coumarins

Nath¹,

Sinha²,

Kumar³

2020

juc

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Heterocyclic nucleus forms the basic of most of the medicinal compounds. Instead of using classical method. It is proposed to carry out the synthesis of heterocyclic compounds by ring transformation that may involve ring contraction, ring retention and ring expansion in five, six and seven membered heterocycles containing oxygen, sulphur and nitrogen. Special attention would be paid to apply the principles of green chemistry while carrying out these ring transformations e.g., choice of safer reagents, use of green catalysts and phase-transfer catalysts whenever necessary. Here a new solid support, Zinc oxide is used. Employing microwave incluced synthesis whenever possible, minimizing the use of toxic solvents. Benzofurans have been achieved from coumarins by ring contraction reaction in single step. Microwave irradiation has been used to shorten the reaction time and to improve the yield.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Fast Synthesis of Benzofurans from Coumarins

Nath¹,

Sinha²,

Kumar³

2020

juc

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“…In addition, benzofuran and its derivative also have antitumor activity against MCF-7 dan PC-3. [15][16][17][18][19] Other compounds that are detected in the methanol extract of G. versteegii Buaya are α-Caryophyllene (6) β-Santalol (7). α-Caryophyllene (6), known as humulene is sesquiterpenes that is found in the essential oil.…”

Section: Gc-ms Analysismentioning

confidence: 99%

Investigation of Anticancer Agents from the Bark of Gyrinops Versteegii (Gilg.) Domke from Lombok Island

et al. 2020

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This study is part of a research collaboration between Kyoto University and The University of Mataram, aiming to identify and to utilize the agarwood plants, i.e., Gyrinops versteegii from Indonesia. The study, specifically, aims to discover anticancer agents from the bark of G. versteegii from Lombok Island of Indonesia. There were three provenances of G. versteegii observed, namely Soyun, Pantai, and Buaya. Based on the Brine Shrimp Lethality Test (BSLT), G. versteegii Buaya showed the highest cytotoxicity with LC50 45,94 µg/ml. Meanwhile, G. versteegii Soyun and Pantai have LC50 75.86 µg/mL and 56.36 µg/mL respectively. A phytochemical study showed that the methanol extract of G. versteegii Buaya containing compounds from the group of alkaloid, flavonoid, steroid, triterpenoid, and saponin. The methanol extracts fractionated using Vacuum Liquid Chromatography into 10 fractions (F1-F10) and then retested BSLT. Among the fractions, F2 showed the best potency as an anticancer with LC50 64,12 µg/mL. Based on the GC-MS analysis, the cytotoxicity from both methanol extract and F2 is predicted to be influenced by the same compounds, namely, 1,4-Benzenediol,2-methyl, Pyridoxylamine, 2,3-Dimethylhydroquionone, Tetramethyl-p-benzoquinone, and Benzofuran. Overall, the bark of G. versteegii from Lombok Island has great potency as an anticancer.

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“…In recent years, natural- and synthetic furan-based ( Figure 1 ) based chemotherapeutic agents have attracted the attention of medicinal chemists to develop novel pharmacological agents with diverse pharmacophores andhave expanded the scope and treatment of various diseases [ 1 , 2 , 3 ].…”

Section: Introductionmentioning

confidence: 99%

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

et al. 2022

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Ultrasound- and microwave-assisted green synthetic strategies were applied to furnish benzofuran–oxadiazole 5a–g and benzofuran–triazole 7a–h derivatives in good to excellent yields (60–96%), in comparison with conventional methods (36–80% yield). These synthesized derivatives were screened for hemolysis, thrombolysis and anticancer therapeutic potential against an A549 lung cancer cell line using an MTT assay. Derivatives 7b (0.1%) and 5e (0.5%) showed the least toxicity against RBCs. Hybrid 7f showed excellent thrombolysis activity (61.4%) when compared against reference ABTS. The highest anticancer activity was displayed by the 5d structural hybridwith cell viability 27.49 ± 1.90 and IC50 6.3 ± 0.7 μM values, which were considerably lower than the reference drug crizotinib (IC50 8.54 ± 0.84 μM). Conformational analysis revealed the spatial arrangement of compound 5d, which demonstrated its significant potency in comparison with crizotinib; therefore, scaffold 5d would be a promising anticancer agent on the basis of cytotoxicity studies, as well as in silico modeling studies.

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Synthesis of New Derivatives of Benzofuran as Potential Anticancer Agents

Cited by 30 publications

References 23 publications

Fast Synthesis of Benzofurans from Coumarins

Fast Synthesis of Benzofurans from Coumarins

Investigation of Anticancer Agents from the Bark of Gyrinops Versteegii (Gilg.) Domke from Lombok Island

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

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