487-52-5Relevant articles and documents
Exploring the 2′-hydroxy-chalcone framework for the development of dual antioxidant and soybean lipoxygenase inhibitory agents
Detsi, Anastasia,Hadjipavlou-Litina, Dimitra,Karadendrou, Maria-Anna,Kostopoulou, Ioanna,Kritsi, Eftichia,Liargkova, Thalia,Polyzos, Nestor-Ioannis,Pontiki, Eleni,Tzani, Andromachi,Zoumpoulakis, Panagiotis
, (2021/05/29)
2′-hydroxy-chalcones are naturally occurring compounds with a wide array of bioactiv-ity. In an effort to delineate the structural features that favor antioxidant and lipoxygenase (LOX) inhibitory activity, the design, synthesis, and bioactivity profile of a series of 2′-hydroxy-chalcones bearing diverse substituents on rings A and B, are presented. Among all the synthesized derivatives, chalcone 4b, bearing two hydroxyl substituents on ring B, was found to possess the best combined activity (82.4% DPPH radical scavenging ability, 82.3% inhibition of lipid peroxidation, and satisfac-tory LOX inhibition value (IC50 = 70 μM). Chalcone 3c, possessing a methoxymethylene substituent on ring A, and three methoxy groups on ring B, exhibited the most promising LOX inhibitory activity (IC50 = 45 μM). A combination of in silico techniques were utilized in an effort to explore the crucial binding characteristics of the most active compound 3c and its analogue 3b, to LOX. A common H-bond interaction pattern, orienting the hydroxyl and carbonyl groups of the aromatic ring A towards Asp768 and Asn128, respectively, was observed. Regarding the analogue 3c, the bulky (-OMOM) group does not seem to participate in a direct binding, but it induces an orientation capable to form H-bonds between the methoxy groups of the aromatic ring B with Trp130 and Gly247.
Biocatalytic green alternative to existing hazardous reaction media: Synthesis of chalcone and flavone derivatives via the Claisen-Schmidt reaction at room temperature
Tamuli, Kashyap J.,Sahoo, Ranjan K.,Bordoloi, Manobjyoti
supporting information, p. 20956 - 20965 (2020/12/31)
Owing to the increasing amount of waste materials around the globe, the conversion of waste or secondary by-products to value-added products for various applications has gained significant interest. Herein, two novel agro-food waste products, Musa sp. 'Malbhog' peel ash (MMPA) and Musa Champa Hort. ex Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon-carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly characterized using different sophisticated analytical techniques such as Fourier-transform infrared spectroscopy (FT-IR), X-ray diffractometry (XRD), Brunauer-Emmett-Teller analysis (BET), Raman spectroscopy, scanning electron microscopy energy dispersive X-ray spectroscopy (SEM-EDS), transition electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) along with element detection using atomic absorption spectroscopy and ion chromatographic methods. These two approaches are metal free, as well as being devoid of any extra additives, co-catalysts, harsh conditions, the use of column chromatography for purification and result in a higher yield of the product within a short space of time. The catalytic abilities of the promoter were also examined to synthesize important bioactive molecules such as butein and apigenin at room temperature. With gram scale synthesis of the chalcone derivatives, the used catalysts (MMPA and MCPA) were further reused for five cycles and did not demonstrate any loss in catalytic activity.
A synthesis method of fisetin
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Paragraph 0017; 0051; 0060-0061; 0066; 0075-0076; 0081-0151, (2019/04/10)
The invention provides a method for synthesis of fisetin, solves the fisetin synthetic method only is suitable for the laboratory, and the product yield and content can't problem. The synthetic method comprises the following steps: 1) using 2 - butanone, benzyl chloride, 2, 4 - dihydroxy acetophenone and anhydrous K2 CO3 Generating on the protecting group of the intermediate product; 2) under the protection of nitrogen, in the alkaline environment, the intermediate product and protocatechuic aldehyde condensation reaction, generating 3 ', 4' - dihydroxy - 7 - [...]; 3) the 3 ', 4' - dihydroxy - 7 - [...] reduction generating 3 ', 4', 7 - three hydroxy chalcone; 4) the 3 ', 4', 7 - three hydroxy chalcone is placed on in the alkaline environment of hydroxy, then in toluene sulfonic acid catalysis of a cyclization reaction, generating fisetin. The synthesis method can be used for industrial production; the synthetic method is simple in operation, raw materials are easy, and the production cost is low, and the resulting intermediate product and finally the yield of the product, the higher the purity, has good prospects for development.
