Synthesis and Antibacterial Activity Study of C-3 α, β-Unsaturated Ketone Linked Benzofuran Derivatives

Liu, Wenlu; Jiang, Xizhen

doi:10.4172/2161-0401.1000164

Cited by 4 publications

(1 citation statement)

References 19 publications

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“…A hydroxyl group on the phenyl ring enhances antibacterial effects [20]. The mechanism of the bactericidal action is thought to be due to disruption of intermolecular interactions.…”

Section: Discussionmentioning

confidence: 99%

Synthesis, characterization and evaluation of antiinflammatory properties of novel α, β-unsaturated ketones

Alrubaie¹,

Muhasin²,

Mousa³

2020

Trop. J. Pharm Res

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Purpose: To prepare and characterize alicyclic aromatic chalcone derivatives, and study their antibiotic and anti-inflammatory properties.Methods: Claisen-Schmidt (aldol condensation) base-catalyzed condensation was used for preparation of chalcone derivatives (compounds I - IV), and the products were characterized using ultraviolet-visible spectroscopy (UV), FT-IR spectroscopy, proton nuclear magnetic resonance (1H-NMR), carbone 13CNMR and mass spectroscopy (MS). The antibacterial effect of the compounds was determined against Baci. cereus, Staph. Aureus, E. coli, and Pseudomonas Aeruginosa. In addition, their anti-inflammatory effects were assayed using cotton granule-induced granuloma in mice. The results were compared with those for diclofenac, a standard drug. The synthesized derivatives were subjected to theoretical studies on their stabilities, and some chemical parameters were calculated using density function theory [DFT].Results: Using Claisen-Schmidt reaction, it was possible to prepare stable chalcone derivatives, such as derivatives of 2-(3-phenyl acryloyl)cyclopentan-1-one, with good results. Depending on the substituted group, it was also shown that the derivatives had effective biological effects. Compound IV displayed a noticeable antibacterial effect against Staph. aureus and E. coli. The prepared chalcone derivatives exerted markedly variable anti-inflammatory effects.Conclusion: These results indicate that Claisen-Schmidt reaction is not limited to the preparation of chalcone derivatives from diphenyl structures only. Stable alicyclic aromatic structures can also be used. This results in derivatives with good biological effects. Keywords: Chalcones, Claisen-Schmidt, Anti-inflammatory effects, Granuloma, Aldol Condensation

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“…A hydroxyl group on the phenyl ring enhances antibacterial effects [20]. The mechanism of the bactericidal action is thought to be due to disruption of intermolecular interactions.…”

Section: Discussionmentioning

confidence: 99%

Synthesis, characterization and evaluation of antiinflammatory properties of novel α, β-unsaturated ketones

Alrubaie¹,

Muhasin²,

Mousa³

2020

Trop. J. Pharm Res

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Approach to the Core Structure of Schweinfurthin B

Roos

Maier

2020

ChemistrySelect

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We investigated approaches to the xanthene part of schweinfurthin B. Starting from an exo‐methylene cyclohexanone, an organocuprate addition led to a cyclohexanone featuring a functionalized benzyl substituent in the 2‐position. Ring‐closing reactions to the tetrahydroxanthene core (formation of the central ring) were possible in moderate yield by attack of a phenolic oxygen function on the keto group. More effective was the cyclization to the xanthene core structure after conversion of the cyclohexanone to the exo‐methylene cyclohexane derivative and Lewis acid mediated addition of the phenolic OH to the double bond. In addition, we tried to form the xanthene ring system in a model study by cycloaddition reaction of a silyl enol ether with an ortho‐quinone methide.

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Palladium-Catalyzed Tandem C–H Functionalization/Cyclization Strategy for the Synthesis of 5-Hydroxybenzofuran Derivatives

et al. 2016

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A palladium-catalyzed benzoquinone C-H functionalization/cyclization strategy with terminal alkynes was employed for the synthesis of some biologically relevant 2,3-disubstituted 5-hydroxybenzofuran derivatives. The benzoquinone acts as a reactant as well as an oxidant. During the process, an additional alkyne functionality can be introduced at the C3 position of the benzofuran. Base, ligand, and external oxidant are not required in this protocol.

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Synthesis and Antibacterial Activity Study of C-3 α, β-Unsaturated Ketone Linked Benzofuran Derivatives

Cited by 4 publications

References 19 publications

Synthesis, characterization and evaluation of antiinflammatory properties of novel α, β-unsaturated ketones

Synthesis, characterization and evaluation of antiinflammatory properties of novel α, β-unsaturated ketones

Approach to the Core Structure of Schweinfurthin B

Palladium-Catalyzed Tandem C–H Functionalization/Cyclization Strategy for the Synthesis of 5-Hydroxybenzofuran Derivatives

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