PL240960B1 - 7,4'-di-O-hexylnaringenin oxime and method of its preparation - Google Patents
7,4'-di-O-hexylnaringenin oxime and method of its preparation Download PDFInfo
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- PL240960B1 PL240960B1 PL434616A PL43461620A PL240960B1 PL 240960 B1 PL240960 B1 PL 240960B1 PL 434616 A PL434616 A PL 434616A PL 43461620 A PL43461620 A PL 43461620A PL 240960 B1 PL240960 B1 PL 240960B1
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- hexylnaringenin
- oxime
- alcohol
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- 238000000034 method Methods 0.000 title claims abstract description 15
- 150000002923 oximes Chemical class 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims abstract description 5
- 229940040526 anhydrous sodium acetate Drugs 0.000 claims abstract description 5
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- 239000012043 crude product Substances 0.000 claims abstract description 4
- 239000005457 ice water Substances 0.000 claims abstract description 4
- 239000002244 precipitate Substances 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 3
- 239000000758 substrate Substances 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000004440 column chromatography Methods 0.000 description 2
- FTVWIRXFELQLPI-ZDUSSCGKSA-N (S)-naringenin Chemical group C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 FTVWIRXFELQLPI-ZDUSSCGKSA-N 0.000 description 1
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 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
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 238000011319 anticancer therapy Methods 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940117954 naringenin Drugs 0.000 description 1
- WGEYAGZBLYNDFV-UHFFFAOYSA-N naringenin Natural products C1(=O)C2=C(O)C=C(O)C=C2OC(C1)C1=CC=C(CC1)O WGEYAGZBLYNDFV-UHFFFAOYSA-N 0.000 description 1
- 235000007625 naringenin Nutrition 0.000 description 1
- 150000002795 naringenin derivatives Chemical class 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Przedmiotem zgłoszenia jest związek o nazwie: Oksym 7,4'-di-O-heksylonaringeniny o wzorze 2 przedstawiony na rysunku. Zgłoszenie obejmuje także sposób otrzymywania oksymu 7,4'-di-O-heksylonaringeniny charakteryzujący się tym, że do substratu, którym jest 7,4'-di-O-heksylonaringenina o wzorze 1 dodaje się chlorowodorek hydroksyloaminy oraz bezwodny octan sodu w stosunku molowym co najmniej 1:1,5:1,5 oraz minimalną ilość alkoholu, co stanowi mieszaninę reakcyjną, którą pozostawia się w temperaturze od 30°C do 55°C na okres od 1 do 48 godzin przy ciągłym mieszaniu, po czym mieszaninę wylewa się do wody z lodem, wytrącony osad sączy się pod zmniejszonym ciśnieniem, a następnie otrzymany surowy produkt oczyszcza się.The subject of the application is the compound named: 7,4'-di-O-hexylnaringenin oxime of the formula 2 presented in the drawing. The application also includes a method for the preparation of 7,4'-di-O-hexylnaringenin oxime characterized in that hydroxylamine hydrochloride and anhydrous sodium acetate are added to the substrate, which is 7,4'-di-O-hexylnaringenin of the formula I, in a molar ratio of hydroxylamine hydrochloride and anhydrous sodium acetate at least 1:1.5:1.5 and a minimum amount of alcohol, which constitutes the reaction mixture, which is left at a temperature of 30°C to 55°C for a period of 1 to 48 hours with continuous stirring, after which the mixture is poured into ice water, the precipitate is filtered under reduced pressure, and then the obtained crude product is purified.
Description
PL 240 960 B1PL 240 960 B1
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest oksym 7,4’-di-O -heksylonaringeniny. Przedmiotem wynalazku jest również sposób otrzymywania oksymu 7,4'-di-O-heksylonaringeniny.The present invention relates to 7,4'-di-O-hexylnaringenin oxime. The invention also relates to a method for the preparation of 7,4'-di-O-hexylnaringenin oxime.
Produkt, według wynalazku może znaleźć zastosowanie jako potencjalny lek w terapii przeciwnowotworowej lub jako środek przeciwdrobnoustrojowy.The product according to the invention may find application as a potential drug in anti-cancer therapy or as an antimicrobial agent.
Znane są doniesienia na temat oksymów O -alkilowych pochodnych naringeniny świadczące o znaczącym wpływie wprowadzenia grupy oksymowej do struktury naringeniny na wzrost aktywności antyproliferacyjnej względem linii komórek nowotworu okrężnicy (HT-29) oraz aktywność przeciwbakteryjną testowaną względem Escherichia coli, Staphylococcus aureus i Bacillus subtilis. (J. Kozłowska et ai,, “Novel O -alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity”, Molecules, 2019, 24(4), 679).There are reports on O-alkyl oximes of naringenin derivatives proving the significant influence of the introduction of the oxime group into the naringenin structure on the increase of antiproliferative activity against the colon cancer cell line (HT-29) and the antibacterial activity tested against Escherichia coli, Staphylococcus aureus and Bacillus subtilis. (J. Kozłowska et ai ,, "Novel O -alkyl Derivatives of Naringenin and Their Oximes with Antimicrobial and Anticancer Activity", Molecules, 2019, 24 (4), 679).
W dostępnej literaturze nie znaleziono doniesień na temat oksymu 7,4’-di-O -heksylonaringeniny i jego sposobu wytwarzania.In the available literature, no reports were found about the 7,4'-di-O-hexylnaringenin oxime and its production method.
Istotą wynalazku jest oksym 7,4’-di-O-heksylonaringeniny.The essence of the invention is 7,4'-di-O-hexylnaringenin oxime.
Istotą jest także sposób otrzymywania oksymu 7,4'-di-O-heksylonaringeniny, polegający na tym, że do 7,4’-di-O-heksylonaringeniny o wzorze 1 dodaje się chlorowodorek hydroksyloaminy oraz bezwodny octan sodu w stosunku molowym co najmniej 1:1,5:1,5 oraz minimalną ilość alkoholu. Stanowi to mieszaninę reakcyjną, którą pozostawia się w temperaturze od 30°C do 55°C na okres od 1 do 48 godzin przy ciągłym mieszaniu. Po tym czasie mieszaninę reakcyjną wylewa się do wody z lodem, a otrzymany osad sączy pod zmniejszonym ciśnieniem. Surowy produkt oczyszcza się.The essence is also the method of obtaining 7,4'-di-O-hexylnaringenin oxime, consisting in adding hydroxylamine hydrochloride and anhydrous sodium acetate in a molar ratio of at least 1 to the 7,4'-di-O-hexylnaringenin of formula 1. : 1.5: 1.5 and the minimum amount of alcohol. This is a reaction mixture which is left at 30 ° C to 55 ° C for 1 to 48 hours with constant stirring. At this time, the reaction mixture was poured into ice-water and the resulting precipitate was filtered under reduced pressure. The crude product is purified.
Korzystne jest, gdy rozpuszczalnikiem organicznym stosowanym do reakcji jest alkohol, zwłaszcza etanol i/lub metanol.It is preferred that the organic solvent used for the reaction is an alcohol, especially ethanol and / or methanol.
Korzystne jest także, gdy temperatura wody do schładzania przereagowanej mieszaniny jest bliska 0°C.It is also advantageous when the temperature of the water for cooling the reacted mixture is close to 0 ° C.
Korzystnym jest, gdy, oczyszczanie prowadzi się na kolumnie chromatograficznej, dodatkowo, gdy eluent stanowi mieszanina chloroformu i metanolu w stosunku objętościowym 100:0,2.It is preferred that the purification is carried out by means of a column chromatography, in addition the eluent is a mixture of chloroform and methanol in a volume ratio of 100: 0.2.
Zasadniczą zaletą wynalazku jest otrzymanie oksymu 7,4’-di-O-heksylonaringeniny z wydajnością sięgającą 99%, z użyciem łatwo dostępnych odczynników.The main advantage of the invention is the preparation of 7,4'-di-O-hexylnaringenin oxime with an efficiency of up to 99%, with the use of readily available reagents.
Sposób wykonania wynalazku objaśniony jest w przykładzie wykonania.The embodiment of the invention is illustrated in an exemplary embodiment.
P r z y k ł a d: W kolbie okrągłodennej zaopatrzonej w mieszadło magnetyczne umieszcza się 0,25 g 7,4’-di-O-heksylonaringeniny o wzorze 1 oraz 0,1183 g chlorowodorku hydroksyloaminy a także 0,1396 g bezwodnego octanu sodu i dodaje się 5 mL bezwodnego etanolu. Reakcję prowadzi się przez 5 godzin w temperaturze 50°C, a kolejne 20 godzin w 40°C. Następnie mieszaninę reakcyjną wylewa się do wody z lodem, a otrzymany osad sączy pod zmniejszonym ciśnieniem. Otrzymany surowy produkt oczyszcza się na kolumnie chromatograficznej stosując, jako eluent mieszaninę chloroformu i metanolu w stosunku objętościowym 100:0,2. Na tej drodze otrzymuje' się 0,2548 g oksymu 7,4'-di-O-heksylonaringeniny w postaci białego proszku z wydajnością 98,6%.Example: 0.25 g of 7.4'-di-O-hexylnaringenin of formula 1 and 0.1183 g of hydroxylamine hydrochloride and 0.1396 g of anhydrous sodium acetate are placed in a round bottom flask equipped with a magnetic stirrer and added 5 mL of anhydrous ethanol. The reaction is carried out for 5 hours at 50 ° C and another 20 hours at 40 ° C. The reaction mixture was then poured into ice-water, and the resulting precipitate was filtered under reduced pressure. The obtained crude product was purified by column chromatography using a 100: 0.2 v / v mixture of chloroform and methanol as eluent. In this way, 0.2548 g of 7,4'-di-O-hexylnaringenin oxime is obtained in the form of a white powder with a yield of 98.6%.
Stałe fizyczne .i spektroskopowe otrzymanego związku, są następujące:The physical and spectroscopic constants of the obtained compound are as follows:
Temp. topnienia (°C): 75-77Temp. mp (° C): 75-77
1H-NMR (600 MHz, Aceton-ds) δ [ppm]: 11,01 (s, 1H, NOH), 10,40 (s, 1H, OH-5), 7,48-7,43 (m, 2H, AA'BB', H-2', H-6'), 7,00-6,96 (m, 2H, H-3', H-5’), 6,05 (d, J = 2,3 Hz, 1 H, H-6), 6,04 (d, J = 2,3 Hz, 1H, H-8), 5,11 (dd, J = 11,9, 3,2 Hz, 1H, H-2), 4,02 (t, J = 6,5 Hz, 2H, -CH2-), 3,97 (t, J = 6,5 Hz, 2H, -CH2-), 3,47 (dd, J = 17,2, 3,2 Hz, 1H, H-3a), 2,81 (dd, J = 17,2, 11,9 Hz, 1H, H-3b), 1,80-1,72 (m, 4H, 2x-CH2-), 1,50-1,44 (m, 4H, 2x-CH2-), 1,37-1,31 (m, 8H, 4x-CH2-), 0,92-0,89 (m, 6H, 2x -CH3);1 H-NMR (600 MHz, Acetone-d s ) δ [ppm]: 11.01 (s, 1H, NOH), 10.40 (s, 1H, OH-5), 7.48-7.43 (m , 2H, AA'BB ', H-2', H-6 '), 7.00-6.96 (m, 2H, H-3', H-5 '), 6.05 (d, J = 2.3 Hz, 1H, H-6), 6.04 (d, J = 2.3 Hz, 1H, H-8), 5.11 (dd, J = 11.9, 3.2 Hz, 1H, H -2), 4.02 (t, J = 6.5 Hz, 2H, -CH2-), 3.97 (t, J = 6.5 Hz, 2H, -CH2-), 3.47 (dd, J = 17.2, 3.2 Hz, 1H, H-3a), 2.81 (dd, J = 17.2, 11.9 Hz, 1H, H-3b), 1.80-1 , 72 (m, 4H, 2x-CH2-), 1.50-1.44 (m, 4H, 2x-CH2-), 1.37-1.31 (m, 8H, 4x-CH2-), 0 , 92-0.89 (m, 6H, 2x -CH3);
13C-NMR (150 MHz,. Aceton-d6) δ [ppm]: 162,96, 160,63, 160,24, 159,33, 154,74 (C = NOH), 132,73, 130,31, 128,66, 115,27, 99,15, 96,61, 95,14, 77,22, 68,67, 68,60, 32,33, 32,28, 30,28, 26,47, 26,39, 23,29, 23,27, 14,31, 14,30; 13 C-NMR (150 MHz, Acetone-d6) δ [ppm]: 162.96, 160.63, 160.24, 159.33, 154.74 (C = NOH), 132.73, 130.31 , 128.66, 115.27, 99.15, 96.61, 95.14, 77.22, 68.67, 68.60, 32.33, 32.28, 30.28, 26.47, 26 , 39, 23.29, 23.27, 14.31, 14.30;
HRMS (m/z): [M + H]+ obliczona dla C27H38NO5, 456,2744; zmierzona 456,2745.HRMS (m / z): [M + H] + calcd for C27H38NO5, 456.2744; measured 456.2745.
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| PL443475A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7,4'-di-O-octylnaringenin oxime and method of obtaining 7,4'-di-O-octylnaringenin oxime |
| PL443474A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7,4'-di-O-nonylnaringenin oxime and method of obtaining 7,4'-di-O-nonylnaringenin oxime |
| PL443473A1 (en) * | 2023-01-13 | 2024-07-15 | Uniwersytet Przyrodniczy we Wrocławiu | 7,4'-di-O-heptylnaringenin oxime and method of obtaining 7,4'-di-O-heptylnaringenin oxime |
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