10-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-3-methyl-1H,10H-pyrano[4,3-b] chromen-1-ones from a pseudo-multicomponent reaction and evaluation of their antioxidant activity

Saher, Liza; Makhloufi‐Chebli, Malika; Dermeche, Leila; Dermeche, Samia; Boutemeur-Khedis, Baya; Rabia, C.; Hamdi, Maâmar; Silva, Artur M. S.

doi:10.1016/j.tet.2018.01.009

Cited by 18 publications

(9 citation statements)

References 36 publications

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“…Subsequently, an intramolecular nucleophilic addition takes place in 25 for accomplishing the annulation of 26 , and the dehydration affords the skeleton of pyrano[4,3‐ b ]chromen‐1‐one ( 27 ). The high ability of 27 to quench DPPH ( 6 ) is attributable to the multiple phenolic ‐OHs in one molecule of 27 , and herein, the Knoevenagel‐related MCRs act as powerful protocols for the integration of aromatic rings [14] …”

Section: Knoevenagel‐related Mcrsmentioning

confidence: 94%

“…If a series of reaction can be accomplished on the basis of the Knoevenagel product within one-pot operation, these tandem reactions are designated as the Knoevenagel-related MCRs. As shown as equation 3in Figure 2, barbituric acid (14) participates in a Knoevenagel reaction with the aldehyde group in 13 (linear form of D-glucose, 12) to give 15, followed by the Michael addition with malononitrile (16). Finally, an intramolecular nucleophilic addition of À CN by À OH occurs in 17 to afford 18, then, the isomerization of 18 accesses to pyrano[2,3-d]pyrimidine-6-carbonitrile (19).…”

Section: Knoevenagel-related Mcrsmentioning

confidence: 99%

“…The high ability of 27 to quench DPPH (6) is attributable to the multiple phenolic -OHs in one molecule of 27, and herein, the Knoevenagel-related MCRs act as powerful protocols for the integration of aromatic rings. [14]…”

Section: Knoevenagel-related Mcrsmentioning

confidence: 99%

“…Recent researches also demonstrate this rule. As shown as equation (14) in Figure 6, 5-amino-1-phenyl-3ethyl-1,2,4-triazole (85) carries out the Groebke 3CR with 4cyanobenzaldehyde (28) and cyclohexyl isocyanide (86) to give a nitrogen-fused imidazo[2,1-c][1,2,4]triazol-5-amine skeleton (87), showing high capacity for quenching DPPH with the aid of multiple nitrogen atoms. [35] Nowadays, the scale of reagent for the Groebke 3CR has been expanded to O-heterocycle.…”

Section: Groebke Reactionmentioning

confidence: 99%

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Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant

Liu

2020

The Chemical Record

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A large number of convincing evidences has revealed the correlation of the pathogeny of diseases with the oxidative damages of DNA, protein, biomembrane, and other biological species, while supplementation of antioxidants is demonstrated to be a promising way to avoid, at least, rectify the unbalance redox status in vivo. Although many endeavors have focused on synthesis of antioxidants, a main hurdle still hinders the wide usages of synthetic antioxidants because of low bioavailability and potential cytotoxicity. The search for antioxidants with multiple functional groups being recognized by different receptors becomes a much sought by researchers, and multicomponent reactions (MCRs) provide with powerful tools for the construction of multifunctional antioxidants. Presented herein is a personal account on the application of MCRs for the synthesis of multifunctional antioxidants, while radical-induced oxidation of DNA acts as the experimental system for evaluating antioxidative effect. Concretely, the Biginelli three-component reaction (3CR) affords such a dihydropyrimidine scaffold that the tautomerization between C=S and CÀ SH leads to antioxidative effect. The Povarov 3CR is able to integrate multiple antioxidative groups, i. e., ferrocenyl and À N(CH 3) 2 , into a quinoline scaffold, while the Groebke 3CR provides with imidazo[1,2-a]pyridine skeleton for inhibiting DNA oxidation. Additionally, the Knoevenagel-related MCRs also become efficient strategies for achieving radical-scavengers. On the other hand, the Ugi 4CR and Passerini 3CR result in the dipeptide and α-acyloxycarboxamide, respectively, with the benefit for the integration of antioxidative features by aliphatic chains. Therefore, MCRs have emerged as efficient tools for integrating multiple antioxidative features into one molecule in order to meet with complicated requirements from various biological surroundings.

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Section: Knoevenagel‐related Mcrsmentioning

confidence: 94%

Section: Knoevenagel-related Mcrsmentioning

confidence: 99%

Section: Knoevenagel-related Mcrsmentioning

confidence: 99%

Section: Groebke Reactionmentioning

confidence: 99%

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Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant

Liu

2020

The Chemical Record

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“…The antioxidant activity (free radical scavenging activity) of the synthesized 5 and 4 was evaluated using the 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH . ) scavenging assay [18,19]. Fig.…”

Section: Antioxidant Activity Assessmentmentioning

confidence: 99%

Selectivity control in the reaction between 2-hydroxyarylaldehydes and 4-hydroxycoumarin. Antioxidant activities and computational studies of the formed products

Lamara

Makhloufi‐Chebli

Benazzouz-Touami

et al. 2021

Journal of Molecular Structure

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Synthesis of Polycyclic Chromene Cores through Gold (I)‐Catalyzed Intramolecular Hydroarylation Reaction (IMHA)

et al. 2021

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A regioselective gold (I)‐catalyzed approach for the construction of polycyclic chromene cores has been developed. The reaction proceeds in good to excellent yields under mild condition with a broad range of substrates providing a simple and efficient tool for the synthesis of pyranochromene derivatives. Moreover, the regiochemical control of the annulation of unsymmetrically substituted propargylic ethers has been investigated focusing on electronic/steric effects of the ligands of gold complexes as well as on the electronic effects of the groups on the aromatic rings.

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10-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-3-methyl-1H,10H-pyrano[4,3-b] chromen-1-ones from a pseudo-multicomponent reaction and evaluation of their antioxidant activity

Cited by 18 publications

References 36 publications

Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant

Multicomponent Reactions for Integrating Multiple Functional Groups into an Antioxidant

Selectivity control in the reaction between 2-hydroxyarylaldehydes and 4-hydroxycoumarin. Antioxidant activities and computational studies of the formed products

Synthesis of Polycyclic Chromene Cores through Gold (I)‐Catalyzed Intramolecular Hydroarylation Reaction (IMHA)

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