ChemInform Abstract: SYNTHESIS AND PHOTO‐INDUCED BIOLOGICAL PROPERTIES OF DEMETHYL DERIVATIVES OF THE NATURAL PYRANOCOUMARINS, XANTHYLETIN OR SESELIN

Faulques, M.; Rene, L.; Royer, Robert E.; Averbeck, D.; Moradi, Mona

doi:10.1002/chin.198325350

Cited by 2 publications

(2 citation statements)

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“…The preparation of pyranocoumarin-3-carboxamide was applied from the previous synthetic strategies reported by Faulgues and colleagues [ 18 ] and was described in Scheme 1 . Commercially available 2,4-dihydroxy benzyldehyde 5 and 3-hydroxy-3-methyl-1-butene 6 were used as the starting materials and were subjected to Lewis acid–promoted Friedel-Crafts alkylation reaction in dioxane with BF 3 -diethylate to obtain the aldehyde 7 in 53% yield as a major product together with many unidentified products [ 19 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity Evaluation of Coumarin-3-Carboxamide Derivatives

et al. 2021

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A series of novel coumarin-3-carboxamide derivatives were designed and synthesized to evaluate their biological activities. The compounds showed little to no activity against gram-positive and gram-negative bacteria but specifically showed potential to inhibit the growth of cancer cells. In particular, among the tested compounds, 4-fluoro and 2,5-difluoro benzamide derivatives (14b and 14e, respectively) were found to be the most potent derivatives against HepG2 cancer cell lines (IC50 = 2.62–4.85 μM) and HeLa cancer cell lines (IC50 = 0.39–0.75 μM). The activities of these two compounds were comparable to that of the positive control doxorubicin; especially, 4-flurobenzamide derivative (14b) exhibited low cytotoxic activity against LLC-MK2 normal cell lines, with IC50 more than 100 μM. The molecular docking study of the synthesized compounds revealed the binding to the active site of the CK2 enzyme, indicating that the presence of the benzamide functionality is an important feature for anticancer activity.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity Evaluation of Coumarin-3-Carboxamide Derivatives

et al. 2021

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“…A similar alkylation using 1-chloro-2-bromoethane furnished the new compound 2,4-bis(2-chloroethoxy)benzaldehyde 10d in 51% yield. Faulques et al 17 reported the preparation of 2-hydroxy-4-(2-propynyloxy)benzaldehyde by using equimolar 2,4-dihydroxy-benzaldehyde and 3-bromo-1-propyne and isolated 2,4-bis(2-propynyloxy)benzaldehyde 10e as a by-product in low yield (7%). We obtained 10e in 90% yield with a 2.3:1 molar ratio of 3-bromo-1-propyne to 2,4-dihydroxybenzaldehyde.…”

Section: Methodsmentioning

confidence: 99%

The preparation of some heteroaromatic and aromatic aldehydes

Katritzky¹,

He²,

Long³

et al. 2000

Arkivoc

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Dedicated to Gurnos AbstractHeteroaromatic α-and β-carboxaldehydes were prepared by the formylation with DMF of α-lithio benzofuran, benzothiophene, N-methylbenzimidazole and 10-methylphenothiazine obtained by direct lithiation and β-lithio compounds from lithium-bromine exchange. Dialkoxybenzaldehydes were prepared by the formylation of dialkoxybenzenes with hexamethylenetetramine (HMTA) or by the alkylation of dihydroxybenzaldehydes with alkyl bromides or iodides.

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ChemInform Abstract: SYNTHESIS AND PHOTO‐INDUCED BIOLOGICAL PROPERTIES OF DEMETHYL DERIVATIVES OF THE NATURAL PYRANOCOUMARINS, XANTHYLETIN OR SESELIN

Cited by 2 publications

References 0 publications

Synthesis and Biological Activity Evaluation of Coumarin-3-Carboxamide Derivatives

Synthesis and Biological Activity Evaluation of Coumarin-3-Carboxamide Derivatives

The preparation of some heteroaromatic and aromatic aldehydes

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