Chromanols, chromanones, and chromones

Saengchantara, S. T.; Wallace, Timothy W.

doi:10.1039/np9860300465

Cited by 126 publications

(45 citation statements)

References 45 publications

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“…27 We have put considerable effort into the development of synthetic strategies for this class of compounds resulting, for example, in an efficient synthetic route to 2-alkyl-substituted chroman-4-ones. 28 The incorporation of various functional groups to furnish highly substituted structures have successfully been conducted through different Pd-mediated cross-coupling reactions, 29,30 through Mannich reactions, 31 and via a SmI 2 –KHMDS-mediated Reformatsky type reaction.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Substituted Chroman-4-one and Chromone Derivatives as Sirtuin 2-Selective Inhibitors

et al. 2012

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A series of substituted chromone/chroman-4-one derivatives has been synthesized and evaluated as novel inhibitors of SIRT2, an enzyme involved in aging-related diseases, e.g., neurodegenerative disorders. The analogues were efficiently synthesized in a one-step procedure including a base-mediated aldol condensation using microwave irradiation. The most potent compounds, with inhibitory concentrations in the low micromolar range, were substituted in the 2-, 6-, and 8-positions. Larger, electron-withdrawing substituents in the 6- and 8-positions were favorable. The most potent inhibitor of SIRT2 was 6,8-dibromo-2-pentylchroman-4-one with an IC50 of 1.5 μM. The synthesized compounds show high selectivity toward SIRT2 over SIRT1 and SIRT3 and represent an important starting point for the development of novel SIRT2 inhibitors.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Substituted Chroman-4-one and Chromone Derivatives as Sirtuin 2-Selective Inhibitors

et al. 2012

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“…Proposed Reaction Mechanism for Production of 3 30) We next focused on the reactivity of 2-(2-hydroxyphenyl)acetates as the bis-nucleophile. By introducing phenolic oxygen and a carbon moiety as the nucleophilic part within the substrate, we thought that substituted chromans, common structures in many pharmaceutical and agricultural compounds, [31][32][33] could be synthesized in one step. The initial attempts were carried out using 1,3-diphenylprop-2-ynyl methyl carbonate (13a) and methyl 2-(2-hydroxyphenyl)acetate (14a).…”

Section: Diastereoselective Construction Of Tetrahydrobenzofuran Skelmentioning

confidence: 99%

Development of Palladium-Catalyzed Transformations Using Propargylic Compounds

Yoshida

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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It is known that propargylic compounds having an ester and a halide at the propargylic positions react with palladium complexes leading to π-propargylpalladium and allenylpalladium complexes, which cause various transformations in the presence of the reactants. The aim of the present study was to develop novel palladium-catalyzed transformations using propargylic compounds. As diastereoselective reactions of propargylic compounds with bis-nucleophiles, we have developed palladium-catalyzed reactions of propargylic carbonates with 2-substituted cyclohexane-1,3-diones, 2-(2-hydroxyphenyl)acetates and 2-oxocyclohex-3-enecarboxylates. These processes produce highly substituted cyclic compounds in a highly stereoselective manner. Through our studies on the construction of substituted 2,3-allenols by the reactions of propargylic oxiranes, it has been made clear that palladium-catalyzed coupling reactions occur in the presence of arylboronic acids and terminal alkynes. The processes can be carried out in mild conditions to yield substituted 4-aryl-2,3-allenols in a diastereoselective manner. In our attempt to develop CO 2 -recycling reactions, we developed a methodology for the synthesis of cyclic carbonates by palladium-catalyzed reactions of propargylic carbonates with phenols. Our findings suggested that the process proceeds through a pathway involving decarboxylation-followed fixation of the liberated CO 2 . Diastereoselective, enantioselective, and enantiospecific construction of cyclic carbonates have been achieved by the application of this methodology.

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“…Oxygenated 2-methylchromones are widespread in nature [210]. The crude extracts of the plant-material containing such constituents are used in India folk medicine for a variety of oilments [211].…”

Section: Benzo Derivatives Of a Six-membered Ring With One Heteroatommentioning

confidence: 99%

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

Madkour¹,

Elgazwy

2007

COC

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New developments in the utilities of some carbon nucleophiles in heterocyclic synthesis are reviewed. General synthetic routes based on the utilization of carbon nucleophiles of active methylene are discussed. The major methods and modifications are analyzed. Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into a structure, probably the use of a carbon nucleophile analogues are the most direct one. The present review deals with the generation and synthetic of carbon nucleophile, which uses as scaffold for the heterocyclic synthesis, and can be considered as an update review. Therefore the only references published upon the second quarter of 2003 are included, and the same restrictions to the literature coverage apply.

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Chromanols, chromanones, and chromones

Cited by 126 publications

References 45 publications

Synthesis and Evaluation of Substituted Chroman-4-one and Chromone Derivatives as Sirtuin 2-Selective Inhibitors

Synthesis and Evaluation of Substituted Chroman-4-one and Chromone Derivatives as Sirtuin 2-Selective Inhibitors

Development of Palladium-Catalyzed Transformations Using Propargylic Compounds

Utilities of Some Carbon Nucleophiles in Heterocyclic Synthesis

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