Synthesis and antimicrobial activity of new benzofuranyl-1,3-benzoxazines and 1,3-benzoxazin-2-ones

Ujjinamatada, Ravi K.; Appala, Raju S.; Agasimundin, Yankanagouda S.

doi:10.1002/jhet.5570430226

Cited by 21 publications

(3 citation statements)

References 8 publications

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“…Ailanthoidol, a neolignan derivative, has been reported to have antiviral, antioxidant and antifungal activities [4]. Furthermore, most of compounds prepared from 2acetylbenzofurans have antimicrobial, antitumor, antiinflammatory, fungicidal, and weed-killing activities and may be used for treatment of cardiac arrhythmias [5][6][7][8][9][10][11][12]. It was observed from the literature that certain five membered heterocyclic compounds possess interesting biological activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Molecular Docking Studies of Novel 2-(5- Bromobenzofuran-2-Yl)-5-Substitutedphenyl-1,3,4-Oxadiazole Derivatives

Sanjeeva

Rao

Ramana

et al. 2021

JASR

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A series of 2-(5-bromobenzofuran-2-yl)-5-substitutedphenyl-1,3,4-oxadiazoles were synthesized in good yields using 5- bromobenzofuran-2-carbohydrazide and characterized by analytical and spectral data. Auto Dock 4.0/ADT program was used to investigate binding interaction of oxadiazole derivatives to Asp kinase. Asp kinase of Mycobacterium tuberculosis (MTB) is a type II topoisomerase and is a well-established and validated target for the development of novel therapeutics. The search was based on the Lamarckian genetic algorithm and the results were analyzed using binding energy. Analysis was based on lowest docked energy and inhibition constant values. Among the tested compounds, 3g, 3a, 3hand 3f derivatives of oxadiazole showed highest binding energy with the lowest inhibition constant. From the observed results it is concluded that 3g, 3a, 3h and 3f showed more affinity to Asp Kinase protein.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Molecular Docking Studies of Novel 2-(5- Bromobenzofuran-2-Yl)-5-Substitutedphenyl-1,3,4-Oxadiazole Derivatives

Sanjeeva

Rao

Ramana

et al. 2021

JASR

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“…Some benzofurans bearing various substituents at the C-2 position are greatly distributed in nature; for example, ailanthoidol, a neolignan derivative, has been reported to have antiviral, antioxidant, and antifungal activities [28]. Furthermore, most of the compounds prepared from 2acetylbenzofuran have antimicrobial, anticancer, antitumor, anti-inflammatory, and antitubulin activities and are also used for treatment of cardiac arrhythmias [29][30][31][32]. The use of the combinations of different pharmacological compounds in the design of new drugs may lead to finding novel drugs with interesting biological activity [33,34].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Anticancer Activity of New Benzofuran Substituted Chalcones

Coskun

Tekin

Sandal

et al. 2016

Journal of Chemistry

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Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties. A novel series of chalcones, 3-aryl-1-(5-bromo-1-benzofuran-2-yl)-2-propanones propenones (3a–f), were designed, synthesized, and characterized.In vitroantitumor activities of the newly synthesized (3a–f) and previously synthesized (3g–j) chalcone compounds were determined by using human breast (MCF-7) and prostate (PC-3) cancer cell lines. Antitumor properties of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Cell viability assay for the tested chalcone compounds was performed and thelog⁡IC50values of the compounds were calculated after 24-hour treatment. Our results indicate that the tested chalcone compounds show antitumor activity against MCF-7 and PC-3 cell lines (p<0.05).

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“…The introduction of a methyl substituent at the metho -position and electron-withdrawing substituent led to a lower conversion (entries 5–9), and the corresponding uncyclization byproducts 4 were detected. Benzofuran-substituted α,β-unsaturated ketone 1m was tolerable, delivering the corresponding cyclization product 3mb in 99% yield and 89% ee, whose structure shows a broad spectrum of biological activities (entry 13). The substituent at the β-aryl group had an effect on the outcomes depending on both the electronic nature and position of the substituent (entries 14–18).…”

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confidence: 99%

Organocatalytic Asymmetric Cascade Reaction of 2-Hydroxyphenyl-Substituted Enones and Isocyanates To Construct 1,3-Benzoxazin-2-ones

et al. 2016

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The development of a new bisguanidinium salt as a multifunctional organocatalyst for asymmetric cascade esterification/aza-Michael reaction between 2-hydroxyphenyl-substituted enones and isocyanates is reported. A high level of enantioinduction and excellent isolated yields were achieved under mild reaction conditions. Enantiomerically enriched 1,3-benzoxazin-2-ones were constructed, and a possible catalytic model was suggested based on the mechanism-driven experiments.

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Synthesis and antimicrobial activity of new benzofuranyl-1,3-benzoxazines and 1,3-benzoxazin-2-ones

Abstract: New benzofuranyl‐1,3‐benzoxazines and 1,3‐benzoxazin‐2‐ones are synthesized in which benzofuran is coupled with 1,3‐benzoxazines and 1,3‐benzoxazin‐2‐ones through ‐CONH‐ and ‐COCH2‐ bridges, respectively. The antimicrobial activity of these compounds is reported.

Cited by 21 publications

References 8 publications

Synthesis, Characterization and Molecular Docking Studies of Novel 2-(5- Bromobenzofuran-2-Yl)-5-Substitutedphenyl-1,3,4-Oxadiazole Derivatives

Synthesis, Characterization and Molecular Docking Studies of Novel 2-(5- Bromobenzofuran-2-Yl)-5-Substitutedphenyl-1,3,4-Oxadiazole Derivatives

Synthesis, Characterization, and Anticancer Activity of New Benzofuran Substituted Chalcones

Organocatalytic Asymmetric Cascade Reaction of 2-Hydroxyphenyl-Substituted Enones and Isocyanates To Construct 1,3-Benzoxazin-2-ones

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