Synthesis of C4-substituted coumarins via Pechmann condensation catalyzed by sulfamic acid. Insights into the reaction mechanism by HRMS analysis

Barcellos, Thiago; Moraes, Maiara C.; Lenardão, Eder J.

doi:10.24820/ark.5550190.p011.645

Cited by 3 publications

(2 citation statements)

References 27 publications

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“…SA has been applied in the industry as an acid-cleaning agent and an environmentally friendly substitute for HCl and H 2 SO 4 [25]. Moreover, it has been successfully utilized as a catalyst in numerous organic synthetic reactions [26][27][28].…”

Section: -Hydroxymethylfurfural (5-hmfmentioning

confidence: 99%

Microwave-Assisted Production of 5-Hydroxymethylfurfural from Fructose Using Sulfamic Acid as a Green Catalyst

Bertoncello Molon,

Ferreira,

Colombo Tedesco

et al. 2024

Sustainability

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The development of safe-by-design synthesis of valuable chemicals from biomass derivatives is a key step towards sustainable chemical transformations in both academia and industry. 5-Hydroxymethylfurfural (5-HMF) is a biomass derivative chemical of high commercial interest due to its wide range of chemical and biofuel applications. In this scenario, the present work contributes to a methodology for producing 5-hydroxymethylfurfural (5-HMF) through fructose dehydration reaction under microwave irradiation. The proposed protocol uses a simple sodium chloride–saturated aqueous-i-PrOH biphasic system and catalysis of sulfamic acid, a low-cost solid Brønsted–Lowry inorganic acid, which presents pivotal features of a sustainable catalyst. A 23 full factorial design was applied to achieve the highest conversion and 5-HMF yield, allowing the identification of the main factors involved in the process. Under the optimized conditions, fructose at the concentration of 120 g L−1 was converted with 91.15 ± 6.98% after 20 min at 180 °C, using 10 mol% of catalyst. 5-HMF was produced in 80.34 ± 8.41% yield and 73.20 ± 8.23% selectivity. Thus, the present contribution discloses a new optimized methodology for converting the biomass derivative fructose to 5-hydroxymethylfurfural (5-HMF).

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Section: -Hydroxymethylfurfural (5-hmfmentioning

confidence: 99%

Microwave-Assisted Production of 5-Hydroxymethylfurfural from Fructose Using Sulfamic Acid as a Green Catalyst

Bertoncello Molon,

Ferreira,

Colombo Tedesco

et al. 2024

Sustainability

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“…The synthetic protocol to obtain the target hybrid compounds started with the Pechmann condensation of the phenols phloroglucinol (1a) and 1-naphthol (1b) with the β-ketoester ethyl 4-chloroacetoacetate (2) to achieve the 4-chloromethylcoumarins 3a and 3b with 86 and 70% yield, respectively. This procedure was carried out in the absence of solvent and using sulfamic acid as catalyst (Moraes, Lenardão & Barcellos, 2021). Then, the azide group was installed by the nucleophilic displacement of the chlorine atom (Naik et al, 2012), affording the 4-(azidomethyl)coumarins 4a and 4b with 89 and 86% yields, respectively, as shown in Figure 2.…”

Section: Chemistrymentioning

confidence: 99%

Novel coumarin-nucleobase hybrids with potential anticancer activity: Synthesis, in-vitro cell-based evaluation, and molecular docking

Moraes

Frassini

Roesch‐Ely

et al. 2023

Preprint

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A new series of compounds planned by molecular hybridization of the nucleobases uracil and thymine, or the xanthine theobromine, with coumarins, and linked through 1,2,3-triazole heterocycles were evaluated for their in vitro anticancer activity against the human tumor cell lines: colon carcinoma (HCT116), laryngeal tumor cells (Hep-2), and lung carcinoma cells (A549). The hybrid compound 7a exhibited better activity in the series, showing an IC50 of 24.19 ± 1.39 μM against the HCT116 cells, with a selectivity index (SI) of 6, when compared to the cytotoxicity against the non-tumor cell line HaCat. Molecular docking studies were performed on all active compounds and suggested that the synthesized compounds possess a high affinity to DNA Topoisomerase-1 protein, supporting their antitumor activity. The in silico toxicity prediction studies suggest that the compounds present a low risk of causing theoretical mutagenic and tumorigenic effects. These findings indicate that the molecular hybridization from natural derivative molecules is an interesting approach to seek new antitumor candidates.

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Novel Coumarin–Nucleobase Hybrids with Potential Anticancer Activity: Synthesis, In Vitro Cell-Based Evaluation, and Molecular Docking

Correa de Moraes,

Frassini,

Roesch-Ely

et al. 2024

Pharmaceuticals

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A new series of compounds planned by molecular hybridization of the nucleobases uracil and thymine, or the xanthine theobromine, with coumarins, and linked through 1,2,3-triazole heterocycles were evaluated for their in vitro anticancer activity against the human tumor cell lines: colon carcinoma (HCT116), laryngeal tumor cells (Hep-2), and lung carcinoma cells (A549). The hybrid compound 9a exhibited better activity in the series, showing an IC50 of 24.19 ± 1.39 μM against the HCT116 cells, with a selectivity index (SI) of 6, when compared to the cytotoxicity against the non-tumor cell line HaCat. The in silico search for pharmacological targets was achieved through molecular docking studies on all active compounds, which suggested that the synthesized compounds possess a high affinity to the Topoisomerase 1–DNA complex, supporting their antitumor activity. The in silico toxicity prediction studies suggest that the compounds present a low risk of causing theoretical mutagenic and tumorigenic effects. These findings indicate that molecular hybridization from natural derivative molecules is an interesting approach to seek new antitumor candidates.

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Synthesis of C4-substituted coumarins via Pechmann condensation catalyzed by sulfamic acid. Insights into the reaction mechanism by HRMS analysis

Cited by 3 publications

References 27 publications

Microwave-Assisted Production of 5-Hydroxymethylfurfural from Fructose Using Sulfamic Acid as a Green Catalyst

Microwave-Assisted Production of 5-Hydroxymethylfurfural from Fructose Using Sulfamic Acid as a Green Catalyst

Novel coumarin-nucleobase hybrids with potential anticancer activity: Synthesis, in-vitro cell-based evaluation, and molecular docking

Novel Coumarin–Nucleobase Hybrids with Potential Anticancer Activity: Synthesis, In Vitro Cell-Based Evaluation, and Molecular Docking

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