Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters

Jeon, Jae Heung; Yang, Deok Mo; Jun, Jong‐Gab

doi:10.5012/bkcs.2011.32.1.65

Cited by 17 publications

(5 citation statements)

References 28 publications

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“…2′-Hydroxychalcone ( 3a ): Obtained from 2′-hydroxyacetophenone (10.31 g, 0.075 mol) and benzaldehyde (8.03 g, 0.075 mol); yield 14.6 g (86%); yellow crystals; mp 77 °C (lit. 75–78 °C [45]) spectroscopic data in accordance with the literature [38].…”

Section: Methodssupporting

confidence: 77%

Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

et al. 2019

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Six γ-oxa-ε-lactones, 4-phenyl-3,4-dihydro-2H-1,5-benzodioxepin-2-one (5a) and its five derivatives with methoxy groups in different positions of A and B rings (5b–f), were synthesized from corresponding flavanones. Three of the obtained lactones (5b,c,f) have not been previously described in the literature. Structures of all synthesized compounds were confirmed by complete spectroscopic analysis with the assignments of signals on 1H and 13C-NMR spectra to the corresponding atoms. In most cases, lactones 5a–f exerted an inhibitory effect on the growth of selected pathogenic bacteria (Escherichia coli, Bacillus subtilis, and Staphylococcus aureus), filamentous fungi (Fusarium graminearum, Aspergillus niger, and Alternaria sp.), and yeast (Candida albicans). The broadest spectrum of activity was observed for unsubstituted lactone 5a, which was particularly active against filamentous fungi and yeast. Lactones with methoxy groups in the 3′ (5c) and 4′ (5d) position of B ring were more active towards bacteria whereas lactone substituted in the 7 position of the A ring (5e) exhibited higher antifungal activity. In most cases, the introduction of lactone function increased the activity of the compound compared to its flavonoid precursors, chalcones 3a–e, and flavanones 4a–f.

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Section: Methodssupporting

confidence: 77%

Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

et al. 2019

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“…E – Z isomerization of cinnamic acid analogues is involved in various established syntheses of coumarin derivatives, including the Perkin, Knoevenagel, and Wittig reactions, and Jeon et al recently reported the preparation of 3,4-dihydrocoumarins via the p -toluenesulfonic acid-catalyzed thermal isomerization and cyclization of cinnamic acid derivatives in sealed tubes at 140 °C. E – Z isomerization is also involved in the biosynthesis of coumarin analogues from o -coumaric acid .…”

Section: Resultsmentioning

confidence: 99%

Elucidating Latent Mechanistic Complexity in Competing Acid-Catalyzed Reactions of Salicylaldehyde-Derived Baylis–Hillman Adducts

et al. 2015

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(1)H NMR-based kinetic studies have revealed the latent mechanistic complexity of deceptively simple hydrochloric acid-catalyzed reactions of salicylaldehyde-derived Baylis-Hillman adducts. Reactions conducted at 0 °C afforded 2-(chloromethyl)cinnamic acid derivatives as the major products and the corresponding 3-(chloromethyl)coumarin derivatives as the minor products. In reactions conducted in refluxing acetic acid, however, the 3-(chloromethyl)coumarin derivatives are the sole products. Variable-temperature (1)H NMR analysis permitted the determination of the rate constants and kinetic parameters involved in the pseudo-first-order formation of (Z)-2-(chloromethyl)-3-(2-hydroxyphenyl)-2-propenoic acid. The kinetic data clearly preclude the operation of classical kinetic versus thermodynamic control and indicate the operation of three independent reaction pathways. Theoretical studies of these pathways undertaken at the B3LYP/6-31G(d) level permitted rationalization of the experimental data and provided insights into the possible mechanism of the enzymic E-Z isomerization and cyclization of (E)-cinnamic acid analogues to afford coumarins.

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“…Docking score were calculated using maestro (Schrodinger) software. The binding affinity was assessed in terms of binding free energies (S-score, kcal/mol) [28]. All synthesized compounds were docked in the groove of binding site present in DNA Gyrase B 5L3J.…”

Section: Molecular Docking Studymentioning

confidence: 99%

Synthesis, Insilico and Antibacterial Activity Studies of Substituted Dihydro-1, 2-Oxazole Benzopyran-2-One Hybrids

D’souza

Kumar

et al. 2021

JPRI

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A series of substituted dihydro-1, 2-oxazole benzopyran-2-one (SR1-SR6) were synthesized through the intermediate substituted benzopyran-2-one chalcones and were characterized using spectral analysis. Compounds were docked with receptor DNA Gyrase B (PDB code: 5L3J) to know its interaction and binding energy; ranges -3.38 to -2.15 kcal/mol. Further these compounds were tested for antibacterial activity using tube dilution method and MIC values were observed; ranges 3.12 to 25 µg/ml. Compound 3-(5-(m-tolyl)-4,5-dihydroisoxazol-3-yl)-2H-chromen-2-one (SR3) showed the best interaction with binding energy -3.38 kcal/mol and antimicrobial activity having MIC 3.12 µg/ml. GRAPHICAL ABSTRACT

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Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters

Cited by 17 publications

References 28 publications

Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

Elucidating Latent Mechanistic Complexity in Competing Acid-Catalyzed Reactions of Salicylaldehyde-Derived Baylis–Hillman Adducts

Synthesis, Insilico and Antibacterial Activity Studies of Substituted Dihydro-1, 2-Oxazole Benzopyran-2-One Hybrids

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