- A synthesis method of fisetin
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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.
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Paragraph 0017; 0051; 0062-0065; 0066; 0077-0080; 0081- 0155
(2019/04/10)
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- Synthesis of fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside based on site-selective deacetylation and deoxygenation
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Fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside were synthesized from commercially available quercetin and naringin in five steps. The key steps are site-selective deacetylation and subsequent deoxygenation. The target molecules were obtained in 37% and 23% yields from the starting materials, respectively.
- Tsunekawa, Ryuji,Hanaya, Kengo,Higashibayashi, Shuhei,Sugai, Takeshi
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p. 1316 - 1322
(2018/07/29)
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- MICROBIAL PRODUCTION OF THE FLAVONOIDS GARBANZOL, RESOKAEMPFEROL AND FISETIN
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The invention provides a genetically modified micro-organism comprising one or more transgene for the production of one or more of the flavonoids garbanzol, resokaempferol and fisetin. The micro-organism may be a bacterial or yeast cell engineered to express a metabolic pathway for garbanzol, resokaempferol and/or fisetin biosynthesis. The invention further provides a method for producing garbanzol, resokaempferol and/or fisetin employing the genetically modified micro-organism of the invention. The genetically modified micro- organism may be used to convert a number of substrates and/or co-substrates into fisetin via a fisetin biosynthetic pathway.
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Page/Page column 41; 42
(2016/06/01)
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- Profiling of flavonol derivatives for the development of antitrypanosomatidic drugs
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Flavonoids represent a potential source of new antitrypanosomatidic leads. Starting from a library of natural products, we combined target-based screening on pteridine reductase 1 with phenotypic screening on Trypanosoma brucei for hit identification. Flavonols were identified as hits, and a library of 16 derivatives was synthesized. Twelve compounds showed EC50 values against T. brucei below 10 μM. Four X-ray crystal structures and docking studies explained the observed structure-activity relationships. Compound 2 (3,6-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one) was selected for pharmacokinetic studies. Encapsulation of compound 2 in PLGA nanoparticles or cyclodextrins resulted in lower in vitro toxicity when compared to the free compound. Combination studies with methotrexate revealed that compound 13 (3-hydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one) has the highest synergistic effect at concentration of 1.3 μM, 11.7-fold dose reduction index and no toxicity toward host cells. Our results provide the basis for further chemical modifications aimed at identifying novel antitrypanosomatidic agents showing higher potency toward PTR1 and increased metabolic stability.
- Borsari, Chiara,Lucian, Rosaria,Pozzi, Cecilia,Poehner, Ina,Henrich, Stefan,Trande, Matteo,Cordeiro-Da-silva, Anabela,Santarem, Nuno,Baptista, Catarina,Tait, Annalisa,Di Pisa, Flavio,Iacono, Lucia Dello,Landi, Giacomo,Gul, Sheraz,Wolf, Markus,Kuzikov, Maria,Ellinger, Bernhard,Reinshagen, Jeanette,Witt, Gesa,Gribbon, Philip,Kohler, Manfred,Keminer, Oliver,Behrens, Birte,Costantino, Luca,Nevado, Paloma Tejera,Bifeld, Eugenia,Eick, Julia,Clos, Joachim,Torrado, Juan,Jiménez-Antón, María D.,Corral, María J.,Alunda, José Ma,Pellati, Federica,Wade, Rebecca C.,Ferrari, Stefania,Mangani, Stefano,Costi, Maria Paola
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p. 7598 - 7616
(2016/09/04)
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- Isolation and synthesis of flavonols and comparison of their antioxidant activity
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Phytochemical investigation of the leaves of Astragalus beckari yielded four flavonol aglycones, namely kaempferol, quercetin, 5-deoxy kaempferol and fisitin. These isolated compounds were then synthesised in the laboratory using the Algar-Flyn-Oyamad reaction. Antioxidant activity of both the isolated and synthesised flavonoids was compared using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay method. The isolated flavonoids were found to be more active.
- Hasan, Aurangzeb,Sadiq,Abbas,Mughal,Khan, Khalid M.,Ali, Muhammad
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experimental part
p. 995 - 1003
(2010/09/05)
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- Novel use of flavones
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A pharmaceutical composition for inhibiting COX-2 biosynthesis comprising a therapeutically effective amount of the compound of formula I and a pharmaceutrically acceptable carrier. wherein R1 and R4 represent either Hydrogen or together a bond R5, R6, R7, R8 represent independently of each other Hydrogen, Hydroxy or Methoxy; in addition R7 represents a sugar substituent like glucoside, rutinosid, manno gluco pyransyl, aprosylglucoside R2 and R3 represent Hydrogen, Hydroxy, Methoxy or wherein R2′, R3′, R4′, R5′ and R6′ are independently or each other Hydrogen, Hydroxy or Methoxy with the proviso, that R2 or R3 is represented by the optionally substituted Phenylring.
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- STEREOCHEMISTRY OF SILYCHRISTIN MILD DEHYDROGENATION OF FLAVANONOLS
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3-Hydroxyflavanones can be quntitatively dehydrogenated by air in pyridine to 2,3-dehydro derivatives.The reaction has been performed on silychristin (1) in order to remove the chirality at the flavanonol ring and to allow the assignment of the stereochemistry of the stereochemistry of the dihydrobenzofuran ring as 2'R,3'S.
- Zanarotti, Antonio
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p. 1585 - 1586
(2007/10/02)
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