PL237332B1 - 4'-hydroxy-7-acetamidoflavone and method for producing 4'-hydroxy-7-acetamidoflavone - Google Patents
4'-hydroxy-7-acetamidoflavone and method for producing 4'-hydroxy-7-acetamidoflavone Download PDFInfo
- Publication number
- PL237332B1 PL237332B1 PL424954A PL42495418A PL237332B1 PL 237332 B1 PL237332 B1 PL 237332B1 PL 424954 A PL424954 A PL 424954A PL 42495418 A PL42495418 A PL 42495418A PL 237332 B1 PL237332 B1 PL 237332B1
- Authority
- PL
- Poland
- Prior art keywords
- acetamidoflavone
- hydroxy
- hours
- organic solvent
- formula
- Prior art date
Links
- OMGUSYCWRZBAGP-UHFFFAOYSA-N N-[2-(4-hydroxyphenyl)-4-oxochromen-7-yl]acetamide Chemical compound C(C)(=O)NC1=CC=C2C(C=C(OC2=C1)C1=CC=C(C=C1)O)=O OMGUSYCWRZBAGP-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000000758 substrate Substances 0.000 claims abstract description 7
- JGSKYGCPGCBEET-UHFFFAOYSA-N 7-amino-2-phenylchromen-4-one Chemical compound C=1C(N)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 JGSKYGCPGCBEET-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000009466 transformation Effects 0.000 claims abstract description 6
- 241000188153 Isaria fumosorosea Species 0.000 claims abstract description 5
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 4
- 241000233866 Fungi Species 0.000 claims abstract description 3
- 230000008569 process Effects 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001093 anti-cancer Effects 0.000 description 3
- 230000036983 biotransformation Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZMFXTDDPSAJSFY-UHFFFAOYSA-N 3-amino-2-phenylchromen-4-one Chemical class O1C2=CC=CC=C2C(=O)C(N)=C1C1=CC=CC=C1 ZMFXTDDPSAJSFY-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- YWHKBWPNCFDUPQ-UHFFFAOYSA-N 6-amino-2-phenylchromen-4-one Chemical compound C=1C(=O)C2=CC(N)=CC=C2OC=1C1=CC=CC=C1 YWHKBWPNCFDUPQ-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930003949 flavanone Natural products 0.000 description 1
- 150000002207 flavanone derivatives Chemical class 0.000 description 1
- 235000011981 flavanones Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 244000052637 human pathogen Species 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 231100000647 material safety data sheet Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Przedmiotem zgłoszenia jest związek o nazwie: 4'-hydroksy-7-acetamidoflawon o wzorze 2 oraz sposób jego otrzymywania. Przedmiotowy sposób ten polega na tym, że do podłoża odpowiedniego dla grzybów strzępkowych wprowadza się szczep Isaria fumosorosea KCH J2. Po upływie co najmniej 72 godzin do hodowli wprowadza się substrat, którym jest 7-aminoflawon o wzorze 1, rozpuszczony w rozpuszczalniku organicznym mieszającym się z wodą. Transformację prowadzi się w temperaturze od 20 do 30 stopni Celsjusza, przy ciągłym wstrząsaniu co najmniej 96 godzin. Kolejno produkt ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą i oczyszcza chromatograficznie.The subject of the application is a compound called: 4'-hydroxy-7-acetamidoflavone of formula 2 and a method of its preparation. The method in question consists in introducing the Isaria fumosorosea KCH J2 strain into a medium suitable for filamentous fungi. After at least 72 hours, the substrate is introduced into the culture, which is 7-aminoflavone of formula 1, dissolved in an organic solvent miscible with water. The transformation is carried out at a temperature of 20 to 30 degrees Celsius, with continuous shaking for at least 96 hours. Next, the product is extracted with an organic solvent immiscible with water and purified by chromatography.
Description
Przedmiotem wynalazku jest 4’-hydroksy-7-acetamidoflawon i sposób wytwarzania 4’-hydroksy-7-acetamidoflawonu o wzorze 2, przedstawionym na rysunku.The present invention relates to 4'-hydroxy-7-acetamidoflavone and the method of producing 4'-hydroxy-7-acetamidoflavone of the formula 2 shown in the drawing.
Związek ten może znaleźć zastosowanie jako antyoksydant w przemyśle spożywczym oraz jako składnik środków farmaceutycznych i kosmetycznych, a także dodatek do pasz.This compound can be used as an antioxidant in the food industry and as a component of pharmaceuticals and cosmetics, as well as a feed additive.
Flawonoidy to drugorzędowe metabolity roślin, które przyjmowane wraz z pokarmami pochodzenia roślinnego odgrywają istotną rolę w prewencji wielu chorób. Związki te wykazują działanie przeciwutleniające, przeciwalergiczne, przeciwzapalne, zapobiegają chorobom układu krążenia, pomagają kontrolować wagę [Raffa, D.; Maggio, B.; Raimondi, M. V.; Plescia, F.; Daidone, G. Recent discoveries of anticancer flavonoids. Eur. J. Med. Chem. 2017, 142, 213-228].Flavonoids are secondary metabolites of plants, which, when ingested with foods of plant origin, play an important role in the prevention of many diseases. These compounds have antioxidant, antiallergic, anti-inflammatory effects, prevent cardiovascular diseases, help control weight [Raffa, D .; Maggio, B .; Raimondi, M.V .; Plescia, F .; Daidone, G. Recent discoveries of anticancer flavonoids. Eur. J. Med. Chem. 2017, 142, 213-228].
Aminoflawony są grupą zyskującą coraz większe zainteresowanie badaczy ze względu na wykazywaną przez nie silną aktywność przeciwnowotworową. Związki te wnikają do komórek rakowych, wewnątrz ulegają aktywacji tworząc pochodne uszkadzające DNA komórek. Jednocześnie aminoflawony nie wykazują działania cytotoksycznego w stosunku do komórek niezmienionych chorobowo [Moorkoth, S. Synthesis and Anti-cancer Activity of Novel Thiazolidinone Analogs of 6-Aminoflavone. Chem. Pharm. Bull 2015, 974, 974-985; Chandrasekaran, S.; Enoch, I. V. M. V. Host-guest interaction of flavanone and 7-aminoflavone with C-Hexylpyrogallol[4]arene. J. Mol. Struct. 2014, 1076, 318-325].Aminoflavones are a group that is gaining more and more interest from researchers due to their strong anti-cancer activity. These compounds penetrate into cancer cells, inside they are activated to form derivatives that damage the DNA of cells. At the same time, aminoflavones do not show any cytotoxic activity towards unchanged cells [Moorkoth, S. Synthesis and Anti-cancer Activity of Novel Thiazolidinone Analogs of 6-Aminoflavone. Chem. Pharm. Bull 2015, 974,974-985; Chandrasekaran, S .; Enoch, I. V. M. V. Host-guest interaction of flavanone and 7-aminoflavone with C-Hexylpyrogallol [4] arene. J. Mol. Struct. 2014, 1076, 318-325].
7-aminoflawon wykazuje działanie antybakteryjne w stosunku do Mycobacterium tuberculosis [Kónya, K.; Pajtas, D.; Kiss-Szikszai, A.; Patonay, T. Buehwald-Hartwig reactions of monohaloflavones. European J. Org. Chem. 2015, 2015, 828-839], a także Staphylococcus aureus i Bacillus typhosus [Bapat, D. S., Venkataraman, F.A.Sc. Potential antitubercular compounds. K. Proc. Indian Acad. Sci. 1955, 336-341, https://doi.org/10.1007/BF03053537].7-aminoflavone shows antibacterial activity against Mycobacterium tuberculosis [Kónya, K .; Pajtas, D .; Kiss-Shikshai, A .; Patonay, T. Buehwald-Hartwig reactions of monohaloflavones. European J. Org. Chem. 2015, 2015, 828-839], as well as Staphylococcus aureus and Bacillus typhosus [Bapat, D. S., Venkataraman, F.A.Sc. Potential antitubercular compounds. K. Proc. Indian Acad. Sci. 1955, 336-341, https://doi.org/10.1007/BF03053537].
W dostępnej literaturze brak jest informacji na temat otrzymywania 4’-hydroksy-7-acetamidoflawonu na drodze syntezy chemicznej i biotransformacji.There is no information in the available literature on the preparation of 4'-hydroxy-7-acetamidoflavone by chemical synthesis and biotransformation.
W ostatnich latach w leczeniu i prewencji chorób coraz większe znaczenie zyskują związki pochodzenia naturalnego i ich odpowiedniki uzyskane na drodze biotransformacji. Dlatego istotne jest poszukiwanie nowych sposobów wytwarzania związków aktywnych biologicznie, które mogą być wykorzystane w przemyśle farmaceutycznym, ale też kosmetycznym i spożywczym.In recent years, compounds of natural origin and their biotransformation counterparts have become more and more important in the treatment and prevention of diseases. Therefore, it is important to search for new methods of producing biologically active compounds that can be used in the pharmaceutical, cosmetic and food industries.
Istotą wynalazku jest 4’-hydroksy-7-acetamidoflawon.The essence of the invention is 4'-hydroxy-7-acetamidoflavone.
Istota otrzymywania 4’-hydroksy-7-acetamidoflawonu polega na tym, że do podłoża odpowiedniego dla grzybów strzępkowych wprowadza się szczep Isaria fumosorosea KCH J2. Po upływie co najmniej 72 godzin do hodowli wprowadza się substrat, którym jest 7-aminoflawon o wzorze 1, rozpuszczony w rozpuszczalniku organicznym mieszającym się z wodą. Transformację prowadzi się w temperaturze od 20 do 30 stopni Celsjusza, przy ciągłym wstrząsaniu co najmniej 96 godzin. Kolejno produkt ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą i oczyszcza chromatograficznie.The essence of obtaining 4'-hydroxy-7-acetamidoflavone is that the Isaria fumosorosea KCH J2 strain is introduced into a medium suitable for filamentous fungi. After at least 72 hours, the substrate is introduced into the culture, which is the 7-aminoflavone of formula I, dissolved in a water-miscible organic solvent. The transformation is carried out at a temperature of 20 to 30 degrees Celsius with continuous shaking for at least 96 hours. Subsequently, the product is extracted with a water-immiscible organic solvent and purified by chromatography.
Korzystnie jest, gdy stosunek masy dodawanego substratu do objętości hodowli wynosi 0,1 mg : 1 mL.Preferably, the ratio of weight of the substrate added to the culture volume to be added is 0.1 mg: 1 mL.
Korzystnie także jest, gdy proces prowadzi się w temperaturze 25 stopni Celsjusza.It is also preferred that the process is carried out at a temperature of 25 degrees Celsius.
Dodatkowo, korzystnie jest, gdy transformację prowadzi się przez 168 godzin.Additionally, it is preferred that the transformation is carried out for 168 hours.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w komórkach szczepu Isaria fumosorosea KCH J2, następuje przekształcenie grupy aminowej do acetamidowej przy C-7 i przyłączenie grupy hydroksylowej w pozycji C-4’. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą (octan etylu).By following the invention, as a result of the action of the enzyme system contained in the cells of the Isaria fumosorosea KCH J2 strain, the amino group is converted to acetamide at C-7 and a hydroxyl group is added at the C-4 'position. The product obtained in this way is separated from the aqueous culture of the microorganism by a known method by extraction with a water-immiscible organic solvent (ethyl acetate).
Zasadniczą zaletą wynalazku jest otrzymanie 4’-hydroksy-7-acetamidoflawonu w temperaturze pokojowej i przy pH naturalnym dla szczepu wykorzystując mikroorganizm niebędący patogenem ludzkim.The main advantage of the invention is the preparation of 4'-hydroxy-7-acetamidoflavone at room temperature and at a natural pH for the strain, using a microorganism that is not a human pathogen.
Wykorzystanie biotransformacji, zamiast syntezy chemicznej, umożliwia, w sposób przyjazny dla środowiska, uzyskanie związków o wyższej biodostępności i aktywności biologicznej, niż użyte substraty (E. Kostrzewa-Susłow, J. Dmochowska-Gładysz, J. Oszmiański, Journal of Molecular Catalysis B: Enzymatic, 2007, 49 (1-4), 113-117, W. A. Loughlin, Bioresource Technology, 2000, 74, 49-62).The use of biotransformation, instead of chemical synthesis, allows in an environmentally friendly way to obtain compounds with higher bioavailability and biological activity than the substrates used (E. Kostrzewa-Susłow, J. Dmochowska-Gładysz, J. Oszmiański, Journal of Molecular Catalysis B: Enzymatic, 2007, 49 (1-4), 113-117, WA Loughlin, Bioresource Technology, 2000, 74, 49-62).
PL 237 332 B1PL 237 332 B1
Wynalazek jest bliżej objaśniony na przykładzie wykonania.The invention is explained in more detail using an exemplary embodiment.
P r z y k ł a d. Do kolby Erlenmajera o pojemności 2000 cm3, w której znajduje się 500 cm3 sterylnej pożywki zawierającej 10 g aminobaku i 30 g glukozy, wprowadza się szczep Isaria fumosorosea KCH J2 ujawniony w zgłoszeniu patentowym o numerze P.416996. Po 96 godzinach jego wzrostu dodaje się 50 mg 7-aminoflawonu o wzorze 1, rozpuszczonego w 1 cm3 tetrahydrofuranu. Transformację prowadzi się w 25 stopniach Celsjusza przy ciągłym wstrząsaniu przez 7 dni. Następnie mieszaninę poreakcyjną ekstrahuje się trzykrotnie octanem etylu, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymany ekstrakt oczyszcza się chromatograficznie, używając jako eluentu mieszaniny chloroformu i metanolu w stosunku 9:1. 4’-Hydroksy-7-acetamidoflawon znajduje się we frakcji o wyższej polarności.Example d. To the Erlenmeyer flask with a capacity of 2,000 cm 3, which is 500 cm 3 of a sterile medium containing 10 g aminobaku and 30 g of glucose, the strain is introduced Isaria fumosorosea MSDS J2 disclosed in Patent Application P.416996. After 96 hours of its growth, 50 mg of 7-aminoflavone I, dissolved in 1 cm 3 of tetrahydrofuran, are added. The transformation is carried out at 25 degrees Celsius with continuous shaking for 7 days. The reaction mixture was then extracted three times with ethyl acetate, dried with anhydrous magnesium sulfate and the solvent was evaporated. The extract obtained is purified by chromatography using a 9: 1 mixture of chloroform and methanol as eluent. 4'-Hydroxy-7-acetamidoflavone is in the higher polarity fraction.
Na tej drodze otrzymuje się 2 mg 4’-hydroksy-7-acetamidoflawonu (wydajność 3%). Stopień konwersji substratu według HPLC >99%In this way, 2 mg of 4'-hydroxy-7-acetamidoflavone are obtained (3% yield). Substrate conversion rate by HPLC> 99%
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi.The obtained product is characterized by the following spectral data.
Opis sygnałów pochodzących z widma 1H NMR (600 MHz, Aceton-d6) δ: 2.17 (s, 3H, -CH3); 6.66 (s, 1H, 3-H); 7.02-7.05 (m, 2H, 3’-H, 5’-H); 7.38 (dd, 1H, J = 8.6, 1.9 Hz, 6-H); 7.94-7.97 (m, 2H, 2’-H, 6’-H); 7.99 (d, 1H, J = 8.6 Hz, 5-H); 8.33 (d, 1H, J = 1.8 Hz, 8-H).Description of signals derived from the 1H NMR spectrum (600 MHz, Acetone-d6) δ: 2.17 (s, 3H, -CH3); 6.66 (s, 1H, 3-H); 7.02-7.05 (m, 2H, 3'-H, 5'-H); 7.38 (dd, 1H, J = 8.6,1.9 Hz, 6-H); 7.94-7.97 (m, 2H, 2'-H, 6'-H); 7.99 (d, 1H, J = 8.6Hz, 5-H); 8.33 (d, 1H, J = 1.8Hz, 8-H).
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL424954A PL237332B1 (en) | 2018-03-19 | 2018-03-19 | 4'-hydroxy-7-acetamidoflavone and method for producing 4'-hydroxy-7-acetamidoflavone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL424954A PL237332B1 (en) | 2018-03-19 | 2018-03-19 | 4'-hydroxy-7-acetamidoflavone and method for producing 4'-hydroxy-7-acetamidoflavone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL424954A1 PL424954A1 (en) | 2019-09-23 |
| PL237332B1 true PL237332B1 (en) | 2021-04-06 |
Family
ID=67979730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL424954A PL237332B1 (en) | 2018-03-19 | 2018-03-19 | 4'-hydroxy-7-acetamidoflavone and method for producing 4'-hydroxy-7-acetamidoflavone |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL237332B1 (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2844511A1 (en) * | 2011-08-11 | 2013-02-14 | Neuprotect Pty Ltd | Flavonoid compounds, and methods of use thereof |
| PL228510B1 (en) * | 2015-11-24 | 2018-04-30 | Univ Przyrodniczy We Wroclawiu | Method for obtaining 6-acetamidoflawone |
| PL228509B1 (en) * | 2015-11-24 | 2018-04-30 | Univ Przyrodniczy We Wroclawiu | Method for obtaining 6-acetamidoflawone |
-
2018
- 2018-03-19 PL PL424954A patent/PL237332B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL424954A1 (en) | 2019-09-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PL234609B1 (en) | 8-O-β-D-4"-methoxyglucopyranosyl-6-methylflavone and method for producing 8-O-β-D-4"-methoxyglucopyranosyl-6-methylflavone | |
| PL237332B1 (en) | 4'-hydroxy-7-acetamidoflavone and method for producing 4'-hydroxy-7-acetamidoflavone | |
| PL237331B1 (en) | Method for producing 7-acetamideflavone | |
| PL237325B1 (en) | 2'-O-β-D-(4"-O-methylglucopyranosyl)-flavone and method for producing 2'-O-β-D-(4"-O-methylglucopyranosyl)-flavone | |
| PL238788B1 (en) | Method of preparing 4'-hydroxy-5,7-dimethoxyflavone | |
| PL237327B1 (en) | 3'-hydroxy-4'-O-β-D-(4"-O-methylglucopyranosyl)-flavone and method for producing 3'-hydroxy-4'-O-β-D-(4"-O-methylglucopyranosyl)-flavone | |
| PL238964B1 (en) | Method of preparing 4'-hydroxy-5,7-dimethoxyflavone | |
| PL238789B1 (en) | Method of preparing 4'-hydroxy-5,7-dimethoxyflavone | |
| PL241535B1 (en) | 6-Methyl-4'-O-β-D-(4"-O-methylglucopyranosyl)-flavanone and method of producing 6-methyl-4'-O-β-D-(4"-O-methylglucopyranosyl)-flavanone | |
| PL237326B1 (en) | 4'-O-β-D-(4"-O-methylglucopyranosyl)-flavone and method for producing 4'-O-β-D-(4"-O-methylglucopyranosyl)-flavone | |
| PL240097B1 (en) | 8-O-β-D-(4"-O-methylglucopyranosyl)-2'-methoxyflavone and method of preparation 8-O-β-D-(4"-O-methylglucopyranosyl)-2'-methoxyflavone | |
| PL238786B1 (en) | 4'-Hydroxy-2',5'-dimethoxyflavone and method of preparing 4'-hydroxy-2',5'-dimethoxyflavone | |
| PL237330B1 (en) | Method for producing 3-O-β-D-glucopyranosyl-3',4',5,7-trihydroxyflavone | |
| PL242469B1 (en) | 3 ', 4'-Dihydroxy-6-hydroxymethylflavanone and 3', 4'-dihydroxy-6-hydroxymethylflavanone production method | |
| PL239720B1 (en) | 6-Chloro-3'-hydroxyflavone and method of producing 6-chloro-3'-hydroxyflavone | |
| PL235963B1 (en) | Method of preparation of 3'-hydroxyflavone | |
| PL242335B1 (en) | 6-Hydroxymethyl-3'-O-β-D-(4'-O-methylglucopyranosyl)-flavanone and method of preparation of 6-hydroxymethyl-3'-O-β-D-(4'-O-methylglucopyranosyl)-flavanone | |
| PL244524B1 (en) | Method for preparing 4'-hydroxymethylflavone | |
| PL244831B1 (en) | Method of preparing 4'-hydroxyflavone | |
| PL242333B1 (en) | 4'-Hydroxy-6-methylene-O-β-D-(4'-O-methylglucopyranosyl)-flavanone and method of preparation of 4'-hydroxy-6-methylene-O-β-D-(4'-O-methylglucopyranosyl)-flavanone | |
| PL241534B1 (en) | 2-Hydroxy-5'-methyl-3-O-β-D-(4''-O-methylglucopyranosyl)-chalcone and method of producing 2-hydroxy-5'-methyl-3-O-β-D-(4"-O-methylglucopyranosyl)-chalcone | |
| PL237709B1 (en) | 3β-Hydroxy-5α-chloro-6,19-oxidoandrostan-17-one and method of preparation of 3β-hydroxy-5α-chloro-6,19-oxidoandrostan-17-one | |
| PL242334B1 (en) | 4'-Hydroxy-6-methyl-3'-O-β-D-(4'-O-methylglucopyranosyl)-flavanone and method of preparation of 4'-hydroxy-6-methyl-3'-O-β-D-(4'-O-methylglucopyranosyl)-flavanone | |
| PL238787B1 (en) | 5'-Hydroxy-2'-methoxyflavone and method of preparing 5'-hydroxy-2'-methoxyflavone | |
| PL239847B1 (en) | 2'-Chloro-7-O-β-D-(4"-O-methylglucopyranosyl)-flavone and method of producing 2'-chloro-7-O-β-D-(4"-O-methylglucopyranosyl)-flavone |