93514-36-4Relevant articles and documents
Base Catalysis for Fine Chemicals Production: Claisen-Schmidt Condensation on Zeolites and Hydrotalcites for Production of Chalcones and Flavanones of Pharmaceutical Interest
Climent, M. J.,Corma, A.,Iborra, S.,Primo, J.
, p. 60 - 66 (1995)
Chalcones and flavanones of commercial interest have been obtained with high yields and selectivities using solid base catalysts derived from hydrotalcites.The Al/(Al + Mg) ratio and hydrotalcite crystallite size are important parameters controlling catalyst activity.These catalysts give better results than acid- (HY) or alkaline-exchanged Y zeolites.An optimized hydrotalcite shows excellent catalytic properties for the synthesis of 2',4,4'-trimethoxychalcone (Vesidryl), a product of pharmaceutical interest.The reactivity of substituted acetophenones and benzaldehyde follows the Hammet correlation.In addition to electronic effects, geometrical effects can also play a role in the reactivity of substituted acetophenones and benzaldehyde.
Glycolytic inhibition and antidiabetic activity on synthesized flavanone scaffolds with computer aided drug designing tools
Kiruthiga, Natarajan,Saravanan, Govindaraj,Selvinthanuja, Chellappa,Sivakumar, Thangavel,Srinivasan, Kulandaivel
, p. 574 - 592 (2021/09/30)
Background: Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs avail-able in the market in long-term use may lead to serious adverse effects. He
Not only AIE: Light-sensitivity of 4-dimethylamino-2′-hydroxychalcones beneficial to highly efficient photochemical synthesis of 4′-dimethylaminoflavanones
Bojarski, Piotr,Kubicki, Aleksander,Mońka, Michal,Serdiuk, Illia E.
, (2020/06/17)
4-dimethylamino-2′-hydroxychalcone in crystals is well known for its aggregation induced emission (AIE) in the red region of spectrum. We however observe that in liquid solutions this dye and its analogues undergo reversible wavelength-dependent light-induced cyclization to the flavanone derivatives. Special care thus should be taken when this compound is used for optoelectronic applications requiring high purity, especially via solution-processed methods. The discussed intramolecular cyclization proceeds faster in nonpolar medium and is quenched completely in the presence of protic solvents or via formation of aggregates in crystal phase. In spite of that quantum yield of a single photoinduced transformation does not exceed 1%, continuous irradiation affords 92% of product which makes it the most efficient preparation route for 4′-dimethylminoflavanone and its derivatives among the ones reported before. According to the DFT and TDDFT calculations supported by the experimentally investigated spectral features, the mechanism of photoinduced formation of a 4′-dimethylaminoflavanone involves several transformations: excited state intramolecular proton transfer (ESIPT), excited and ground state rotational isomerization from s-trans to s-cis isomer, cyclization and enol-keto tautomerization via proton transfer in the ground state.
