PL218841B1 - New 7-propionoxy flavone and method of its manufacturing - Google Patents
New 7-propionoxy flavone and method of its manufacturingInfo
- Publication number
- PL218841B1 PL218841B1 PL397632A PL39763211A PL218841B1 PL 218841 B1 PL218841 B1 PL 218841B1 PL 397632 A PL397632 A PL 397632A PL 39763211 A PL39763211 A PL 39763211A PL 218841 B1 PL218841 B1 PL 218841B1
- Authority
- PL
- Poland
- Prior art keywords
- flavone
- new
- propionoxyflavone
- propionoxy
- manufacturing
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- GDVZSMQVEHBBNG-UHFFFAOYSA-N (4-oxo-2-phenylchromen-7-yl) propanoate Chemical compound C=1C(OC(=O)CC)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 GDVZSMQVEHBBNG-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- MQGPSCMMNJKMHQ-UHFFFAOYSA-N 7-hydroxyflavone Chemical compound C=1C(O)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 MQGPSCMMNJKMHQ-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229930003935 flavonoid Natural products 0.000 description 6
- 150000002215 flavonoids Chemical class 0.000 description 6
- 235000017173 flavonoids Nutrition 0.000 description 6
- 208000005623 Carcinogenesis Diseases 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 230000006907 apoptotic process Effects 0.000 description 3
- 230000036952 cancer formation Effects 0.000 description 3
- 231100000504 carcinogenesis Toxicity 0.000 description 3
- 231100000433 cytotoxic Toxicity 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000001613 neoplastic effect Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229930003944 flavone Natural products 0.000 description 2
- 150000002213 flavones Chemical class 0.000 description 2
- 235000011949 flavones Nutrition 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 102000003390 tumor necrosis factor Human genes 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 241000241413 Propolis Species 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000005809 anti-tumor immunity Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000002113 chemopreventative effect Effects 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000009569 green tea Nutrition 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000006882 induction of apoptosis Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940047124 interferons Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000014399 negative regulation of angiogenesis Effects 0.000 description 1
- 210000005170 neoplastic cell Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229940069949 propolis Drugs 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000020095 red wine Nutrition 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest nowy 7-propionoksyflawon, o wzorze 2, przedstawiony na rysunku, i sposób jego wytwarzania.The subject of the invention is the novel 7-propionoxyflavone of formula II shown in the drawing and a process for its preparation.
Wynalazek może znaleźć zastosowanie w przemyśle farmaceutycznym.The invention may find application in the pharmaceutical industry.
Flawonoidy są związkami obecnymi w przyrodzie, głównie w owocach, warzywach, propolisie, zielonej herbacie, kawie, piwie, czerwonym winie. Liczne eksperymenty in vitro i in vivo potwierdzają znaczenie flawonoidów i ich pochodnych w profilaktyce chorób nowotworowych, a także w hamowaniu kancerogenezy. W ostatnich latach coraz większą rolę przypisuje się flawonoidom i ich pochodnym z uwagi na działanie chemoprewencyjne, która polega na stosowaniu naturalnych lub syntetycznych związków odwracających proces karcynogenezy i/lub działających antyproliferacyjnie na nieprawidłowe komórki organizmu.Flavonoids are compounds found in nature, mainly in fruits, vegetables, propolis, green tea, coffee, beer, red wine. Numerous in vitro and in vivo experiments confirm the importance of flavonoids and their derivatives in the prevention of neoplastic diseases, as well as in the inhibition of carcinogenesis. In recent years, an increasing role has been assigned to flavonoids and their derivatives due to their chemopreventive effect, which consists in the use of natural or synthetic compounds that reverse the carcinogenesis process and / or have antiproliferative effects on abnormal cells in the body.
Obok flawonoidów i ich pochodnych naturalnym czynnikiem przeciwnowotworowym jest ligand czynnika martwicy nowotworu indukującego apoptozę (TRAIL). TRAIL jest cząsteczką, która nie jest toksyczna w stosunku do prawidłowych komórek organizmu i posiada zdolność indukowania apoptozy w komórkach nowotworowych. Te cechy TRAIL wskazują na jego dużą rolę w niszczeniu komórek nowotworowych.In addition to flavonoids and their derivatives, the natural anti-tumor agent is the tumor necrosis factor ligand inducing apoptosis (TRAIL). TRAIL is a molecule that is non-toxic to normal cells in the body and has the ability to induce apoptosis in cancer cells. These features of TRAIL indicate its major role in destroying cancer cells.
Flawonoidy, w tym flawony i ich pochodne podobnie jak cytostatyki, promieniowanie gamma lub interferony mogą nasilać działanie TRAIL w stosunku do komórek nowotworowych. Wykazano, że na przeciwnowotworową aktywność składają się różne efekty i kierunki działania flawonoidów, między innymi: hamowanie proliferacji, modulacja genów i białek regulujących cykl komórkowy, indukcja apoptozy w komórkach nowotworowych, hamowanie angiogenezy a także wspomaganie naturalnych mechanizmów odporności przeciwnowotworowej z udziałem ligandu czynnika martwicy nowotworu indukującego apoptozę (TRAIL).Flavonoids, including flavones and their derivatives, as well as cytostatics, gamma radiation or interferons, may potentiate the effect of TRAIL on neoplastic cells. It has been shown that the antitumor activity consists of various effects and directions of action of flavonoids, including: inhibition of proliferation, modulation of genes and proteins regulating the cell cycle, induction of apoptosis in tumor cells, inhibition of angiogenesis, as well as supporting the natural mechanisms of anti-tumor immunity with the participation of tumor necrosis factor ligand apoptosis inducer (TRAIL).
Brak jest doniesień literaturowych na temat otrzymania 7-propionoksyflawonu.There are no reports in the literature on the preparation of 7-propionoxyflavone.
Istotą wynalazku jest nowy 7-propionoksyflawon, o wzorze 2, przedstawiony na rysunku.The essence of the invention is the novel 7-propionoxyflavone of formula 2 shown in the drawing.
Istotą wynalazku jest także sposób wytwarzania nowego 7-propionoksyflawonu.The essence of the invention is also the method of producing the new 7-propionoxyflavone.
Sposób, według wynalazku, polega na tym, że, 7-hydroksyflawon, o wzorze 1, rozpuszczony w tetrahydrofuranie poddaje się estryfikacji, w pozycji 7-OH, za pomocą chlorku propionylu w obecności pirydyny.The process according to the invention consists in that the 7-hydroxy flavone of formula I dissolved in tetrahydrofuran is esterified at the 7-OH position with propionyl chloride in the presence of pyridine.
Korzystne jest, gdy reakcję estryfikacji prowadzi się, przy ciągłym mieszaniu reagentów, w temperaturze 291-295K.It is advantageous if the esterification reaction is carried out at a temperature of 291-295K under constant stirring of the reactants.
Postępując zgodnie z wynalazkiem, w wyniku działania chlorku propionylu w obecności pirydyny, następuje reakcja estryfikacji pozycji 7-OH 7-hydroksyflawonu. Uzyskany w ten sposób produkt wydziela się z mieszaniny poreakcyjnej, znanym sposobem, przez ekstrakcję octanem etylu.In accordance with the invention, the esterification reaction of the 7-OH position of the 7-hydroxy flavone occurs by the action of propionyl chloride in the presence of pyridine. The product thus obtained is separated from the reaction mixture by extraction with ethyl acetate in a known manner.
Zaletą sposobu, według wynalazku, jest otrzymanie 7-propionoksyflawonu jako jedynego produktu reakcji z wydajnością 96,00%, w temperaturze pokojowej.The advantage of the process according to the invention is that 7-propionoxyflavone is obtained as the sole reaction product with a yield of 96.00% at room temperature.
Związek ten posiada właściwości przeciwnowotworowe, a także wykazuje właściwości przeciwzapalne.This compound has anti-cancer properties and also has anti-inflammatory properties.
W badaniach został oceniony efekt cytotoksyczny 7-propionoksyflawonu w kombinacji z TRAIL. W serii eksperymentów, jako model linii nowotworowej wybrano komórki raka stercza LNCaP.The studies assessed the cytotoxic effect of 7-propionoxyflavone in combination with TRAIL. In a series of experiments, LNCaP prostate cancer cells were chosen as a model of the neoplastic line.
Związek, będący przedmiotem wynalazku, nasilał i wzmacniał cytotoksyczne działanie TRAIL w stosunku do badanych komórek linii nowotworowych.The compound, which is the subject of the invention, potentiated and potentiated the cytotoxic effect of TRAIL against the tested cells of the tumor lines.
Wyniki badań z zastosowaniem skojarzonego działania flawonów i rekombinowanego TRAIL wskazują na potencjalny ich wpływ na końcowy efekt cytotoksyczny.The results of studies using the combined action of flavones and recombinant TRAIL indicate their potential influence on the final cytotoxic effect.
Badania na makrofagach linii RAW 264.7 wykazały również działanie przeciwzapalne związku poprzez hamowanie produkcji tlenku azotu oznaczanego metodą Griess'a.Research on macrophages of the RAW 264.7 line also showed the anti-inflammatory effect of the compound by inhibiting the production of nitric oxide determined by the Griess method.
Związek, będący przedmiotem wynalazku, może zostać wykorzystany, jako składnik preparatów stosowanych w profilaktyce chorób nowotworowych, hamowaniu procesu kancerogenezy a także prewencji wstrząsu septycznego.The compound, which is the subject of the invention, can be used as a component of preparations used in the prophylaxis of neoplastic diseases, inhibition of the carcinogenesis process and prevention of septic shock.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an exemplary embodiment.
PrzykładExample
Do 60.00 mg (0.25 mmola) 7-hydroksyflawonu rozpuszczonego w 5 ml tetrahydrofuranu (THF) dodaje się 0.05 ml (0.62 mmola) pirydyny oraz 0.05 ml (0.58 mmola) chlorku propionylu. Całość miesza się w temperaturze 294K przez 1 godzinę. Postęp reakcji kontroluje się przy użyciu TLC, w układzie rozwijającym heksan:octan etylu, 7:3. Po zakończeniu reakcji do mieszaniny reakcyjnej dodaje się0.05 ml (0.62 mmol) of pyridine and 0.05 ml (0.58 mmol) of propionyl chloride are added to 60.00 mg (0.25 mmol) of 7-hydroxy flavone dissolved in 5 ml of tetrahydrofuran (THF). The mixture is stirred at 294K for 1 hour. The progress of the reaction is monitored by TLC by developing hexane: ethyl acetate, 7: 3. After completion of the reaction, it is added to the reaction mixture
PL 218 841 B1 ml octanu etylu i przemywa 0.5 M roztworem kwasu solnego, do uzyskania odczynu kwaśnego (pH około 5). Warstwę organiczną oddziela się, a warstwę wodną dodatkowo ekstrahuje się octanem etylu (3x5 ml). Połączone roztwory octanowe przemywa się solanką do uzyskania odczynu obojętnego i suszy bezwodnym MgSO4. Po odparowaniu rozpuszczalnika otrzymuje się 71.19 mg czystego 7-propionoksyflawonu, co stanowi 96.00% wydajności teoretycznej.Prepare ml of ethyl acetate and wash with 0.5 M hydrochloric acid until acidic (about pH 5). The organic layer was separated and the aqueous layer was further extracted with ethyl acetate (3 x 5 ml). The combined acetate solutions are washed with brine until neutral and dried with anhydrous MgSO4. After evaporating off the solvent, 71.19 mg of pure 7-propionoxyflavone are obtained, representing 96.00% of theory.
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR (THF-d8) δ: 1,23 (3H, t, J=7,5 Hz, CH3CH2-); 2,64 (2H, q, J=7,5 Hz, CH3CH2-); 6,86 (1H, s, H-3); 7,18 (1H, dd, J=8,6, 1,0 Hz, H-6); 7,50 (1H, d, J=1,0 Hz, H-8); 7,52 (3H, m, H-3', H-4', H-5'); 8,02 (2H, m, J=7,5 Hz, H-2', H-6'); 8,13 (1H,d, J=8,6 Hz, H-5). 1 H NMR (THF-d8) δ: 1.23 (3H, t, J = 7.5 Hz, CH3CH2-); 2.64 (2H, q, J = 7.5Hz, CH3CH2-); 6.86 (1H, s, H-3); 7.18 (1H, dd, J = 8.6, 1.0 Hz, H-6); 7.50 (1H, d, J = 1.0 Hz, H-8); 7.52 (3H, m, H-3 ', H-4', H-5 '); 8.02 (2H, m, J = 7.5Hz, H-2 ', H-6'); 8.13 (1H, d, J = 8.6Hz, H-5).
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL397632A PL218841B1 (en) | 2011-12-29 | 2011-12-29 | New 7-propionoxy flavone and method of its manufacturing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL397632A PL218841B1 (en) | 2011-12-29 | 2011-12-29 | New 7-propionoxy flavone and method of its manufacturing |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL397632A1 PL397632A1 (en) | 2012-08-13 |
| PL218841B1 true PL218841B1 (en) | 2015-02-27 |
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| PL397632A PL218841B1 (en) | 2011-12-29 | 2011-12-29 | New 7-propionoxy flavone and method of its manufacturing |
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| Publication number | Publication date |
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| PL397632A1 (en) | 2012-08-13 |
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