PL238122B1 - Cis-(4R,5R,6S)-5-(1-bromethyl)-4-(2',5'-dimethylphenyl)-dihydrofuran-2-one and method for obtaining it - Google Patents
Cis-(4R,5R,6S)-5-(1-bromethyl)-4-(2',5'-dimethylphenyl)-dihydrofuran-2-one and method for obtaining it Download PDFInfo
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- PL238122B1 PL238122B1 PL425549(22)20180515A PL42554918A PL238122B1 PL 238122 B1 PL238122 B1 PL 238122B1 PL 42554918 A PL42554918 A PL 42554918A PL 238122 B1 PL238122 B1 PL 238122B1
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- dimethylphenyl
- dihydrofuran
- cis
- bromoethyl
- hex
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- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000010722 bromolactonization reaction Methods 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 238000004440 column chromatography Methods 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- -1 (1-bromoethyl) -4- (2 ', 5'-dimethylphenyl) -dihydrofuran-2-one Chemical compound 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- AVSAPYYIFVSGNF-ITKZLYELSA-N (E,3R)-3-(2,5-dimethylphenyl)hex-4-enoic acid Chemical compound CC1=C(C=C(C=C1)C)[C@H](CC(=O)O)\C=C\C AVSAPYYIFVSGNF-ITKZLYELSA-N 0.000 claims 2
- RSMFTPWQSUSOGH-VUDGCMKMSA-N CC1=C(C=C(C=C1)C)[C@H](CC)\C=C\C Chemical compound CC1=C(C=C(C=C1)C)[C@H](CC)\C=C\C RSMFTPWQSUSOGH-VUDGCMKMSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- AVSAPYYIFVSGNF-ZYOFXKKJSA-N (E,3S)-3-(2,5-dimethylphenyl)hex-4-enoic acid Chemical compound CC1=C(C=C(C=C1)C)[C@@H](CC(=O)O)\C=C\C AVSAPYYIFVSGNF-ZYOFXKKJSA-N 0.000 abstract description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 5
- 241000282465 Canis Species 0.000 description 4
- 230000001028 anti-proliverative effect Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000006083 1-bromoethyl group Chemical group 0.000 description 2
- 208000003950 B-cell lymphoma Diseases 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SMUVABOERCFKRW-UHFFFAOYSA-N 2,5-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C)C(C=O)=C1 SMUVABOERCFKRW-UHFFFAOYSA-N 0.000 description 1
- 208000004736 B-Cell Leukemia Diseases 0.000 description 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 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
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007398 colorimetric assay Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Furan Compounds (AREA)
Abstract
Zgłoszenie dotyczy optycznie czynnego cis-(4R,5R,6S)-5-(1-bromoetylo)-4-(2',5'-dimetylofenylo)-dihydrofuran-2-onu o wzorze 1, oraz sposobu jego otrzymywania. Sposób ten polega na tym, że kwas (S,E)-3-(2',5'-dimetylofenylo)-heks-4-enowy poddaje się reakcji bromolaktonizacji otrzymując mieszaninę produktów, z której następnie metodą chromatografii kolumnowej wydziela się w postaci czystej cis-(4R,5R,6S)-5-(1-bromoetylo)-4-(2',5'-dimetylofenylo)-dihydrofuran-2-on.The application relates to optically active cis-(4R,5R,6S)-5-(1-bromoethyl)-4-(2',5'-dimethylphenyl)-dihydrofuran-2-one of formula 1, and a method for its preparation. This method consists in subjecting (S,E)-3-(2',5'-dimethylphenyl)-hex-4-enoic acid to a bromolactonization reaction to obtain a mixture of products, from which cis-(4R,5R,6S)-5-(1-bromoethyl)-4-(2',5'-dimethylphenyl)-dihydrofuran-2-one is then isolated in pure form by column chromatography.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest optycznie czynny c/s-(4R,5R,6S)-5-(1-bromoetylo)-4-(2’,5’-dimetylofenylo)-dihydrofuran-2-on o wzorze 1 przedstawionym na rysunku.The present invention relates to the optically active c / s- (4R, 5R, 6S) -5- (1-bromoethyl) -4- (2 ', 5'-dimethylphenyl) -dihydrofuran-2-one of the formula 1 shown in the drawing.
Przedmiotem wynalazku jest również sposób otrzymywania bromolaktonu o wzorze 1 z kwasu (S,E)-3-(2’,5’-dimetylofenylo)-heks-4-enowego.The invention also relates to a process for the preparation of bromolactone of formula 1 from (S, E) -3- (2 ', 5'-dimethylphenyl) -hex-4-enoic acid.
Optycznie czynny 3-fenylo-5-bromo-y-lakton o wzorze 1 może znaleźć zastosowanie w przemyśle farmaceutycznym jako związek o działaniu antynowotworowym.The optically active 3-phenyl-5-bromo-γ-lactone of the formula I can find application in the pharmaceutical industry as a compound with anti-tumor activity.
ó-Bromo-y-lakton z pierścieniem 2,5-dimetylofenylowym o wzorze 1 wykazuje aktywność antyproliferacyjną in vitro wobec psich nowotworowych linii komórkowych: chłoniaka B-komórkowego (CLBL-1) oraz przewlekłej białaczki B-komórkowej (CLB70). Związek ten może znaleźć zastosowanie w farmacji jako składnik leków anty nowotworowych.β-Bromo-γ-lactone with a 2,5-dimethylphenyl ring of formula 1 shows antiproliferative activity in vitro against canine tumor cell lines: B-cell lymphoma (CLBL-1) and chronic B-cell leukemia (CLB70). This compound may find application in pharmacy as a component of anti-cancer drugs.
Dotychczas znane były optycznie czynne jodolaktony z pierścieniem 2,5-dimetylofenylowym wykazujące aktywność antyproliferacyjną in vitro wobec linii komórkowych: białaczki ludzkiej (Jurkat), psiej białaczki B-komórkowej (GL-1), psiej osteosarkomy (D17) oraz psiego chłoniaka B-komórkowego (CLBL-1) (Gładkowski W., Skrobiszewski A., Mazur M., Gliszczyńska A., Czarnecka M., Pawlak A., Obmińska-Mrukowicz B., Maciejewska G., Białońska A. Chiral 5-iodo-y-lactones derived from cuminaldehyde, 2,5-dimethylbenzaldehyde and piperonal: chemoenzymatic synthesis and antiproliferative activity. Tetrahedron: Asymmetry, 2016, 27, 227-237; opis wynalazku P.415782 oraz P.415783).So far, optically active iodolactones with a 2,5-dimethylphenyl ring have been known, showing antiproliferative activity in vitro against the following cell lines: human leukemia (Jurkat), canine B-cell leukemia (GL-1), canine osteosarcoma (D17) and canine B-cell lymphoma (CLBL-1) (Gładkowski W., Skrobiszewski A., Mazur M., Gliszczyńska A., Czarnecka M., Pawlak A., Obmińska-Mrukowicz B., Maciejewska G., Białońska A. Chiral 5-iodo-y- lactones derived from cuminaldehyde, 2,5-dimethylbenzaldehyde and piperonal: chemoenzymatic synthesis and antiproliferative activity. Tetrahedron: Asymmetry, 2016, 27, 227-237; invention description P.415782 and P.415783).
Wynalazek dotyczy sposobu wytwarzania na drodze syntezy chemicznej optycznie czynnego c/s-(4/?,5/?,6S)-5-(1-bromoetylo)-4-(2',5'-dimetylofenylo)-dihydrofuran-2-onu o wzorze 1 z kwasu (S,E)-3-(2',5'-dimetylofenylo)-heks-4-enowego.The invention relates to a chemical synthesis of the optically active c / s- (4 ', 5', 6S) -5- (1-bromoethyl) -4- (2 ', 5'-dimethylphenyl) -dihydrofuran-2- one of formula I from (S, E) -3- (2 ', 5'-dimethylphenyl) -hex-4-enoic acid.
Istota wynalazku polega na tym, że kwas (S,E)-3-(2',5'-dimetylofenylo)-heks-4-enowy poddaje się reakcji z N-bromoimidem kwasu bursztynowego, a z otrzymanej mieszaniny bromolaktonów wydziela się metodą chromatografii kolumnowej czysty c/s-(4/?,5/?,6S)-5-(1-bromoetylo)-4-(2',5'-dimetylofenylo)dihydrofuran-2-on.The essence of the invention lies in the fact that (S, E) -3- (2 ', 5'-dimethylphenyl) -hex-4-enoic acid is reacted with N-bromosuccinimide, and the resulting mixture of bromolactones is separated by column chromatography. pure c / s- (4 ', 5', 6S) -5- (1-bromoethyl) -4- (2 ', 5'-dimethylphenyl) dihydrofuran-2-one.
Korzystnie jest, gdy reakcję bromolaktonizacji kwasu (S,E)-3-(2’,5’-dimetylofenylo-heks-4-enowego prowadzi się w tetrahydrofuranie.Preferably, the bromolactonization reaction of (S, E) -3- (2 ', 5'-dimethylphenyl-hex-4-enoic acid is carried out in tetrahydrofuran.
Korzystnie jest także, gdy reakcję bromolaktonizacji kwasu (S,E)-3-(2’,5’-dimetylofenylo)-heks-4-enowego prowadzi się w obecności katalitycznych ilości kwasu octowego.It is also preferred that the bromolactonization reaction of (S, E) -3- (2 ', 5'-dimethylphenyl) -hex-4-enoic acid is carried out in the presence of catalytic amounts of acetic acid.
Zasadniczą zaletą wynalazku jest otrzymanie c/s-(4/?,5/?,6S)-5-(1-bromoetylo)-4-(2' 5'-dimetylofenylo)-dihydrofuran-2-onu o wzorze 1 wykazującego aktywność antyproliferacyjną in vitro z bardzo wysokim nadmiarem ensncjomerycznym (ee = 98%).The main advantage of the invention is the preparation of c / s- (4 / ?, 5 / ?, 6S) -5- (1-bromoethyl) -4- (2 '5'-dimethylphenyl) -dihydrofuran-2-one of the formula 1 showing the activity of antiproliferative in vitro with a very high ensniomeric excess (ee = 98%).
Tabela 1 przedstawia wyniki testów biologicznych in vitro otrzymanego laktonu w stosunku do wybranych linii komórek nowotworowych. Testy przeprowadzono według metody opisanej w literaturze (Ferrari M., Fornasiero M.C., Isetta A.M. MTT colorimetric assay fortesting macrophage cytotoxic activity in vitro. Journal of Immunological Methods, 1990, 131, 165-172).Table 1 shows the results of in vitro biological tests of the obtained lactone against selected tumor cell lines. The tests were performed according to the method described in the literature (Ferrari M., Fornasiero M.C., Isetta A.M. MTT colorimetric assay fortesting macrophage cytotoxic activity in vitro. Journal of Immunological Methods, 1990, 131, 165-172).
Tabela 1Table 1
ICsj - stężenie związku, przy którym żywotność komórek wynosi 50%ICsj - concentration of the compound at which cell viability is 50%
SEM - błąd standardowy średniejSEM - standard error of the mean
Wynalazek jest bliżej objaśniony w przykładzie wykonaniaThe invention is explained in more detail in an exemplary embodiment
Przykład. W kolbie okrągłodennej umieszcza się 1,6 g kwasu (S,E)-3-(2',5'-dimetylofenylo)heks-4-enowego, 2,5 g N-bromoimidu kwasu bursztynowego (NBS), 50 cm3 THF i kroplę kwasu octowego. Całość miesza się na mieszadle magnetycznym w temperaturze pokojowej kontrolując przebieg reakcji za pomocą chromatografii cienkowarstwowej heksan : aceton w stosunku objętościowym 7:1. Po. całkowitym przereagowaniu substratu całość przenosi się do rozdzielacza, rozcieńcza 30 cm3 eteru dietylowego i przemywa nasyconym roztworem NaHCOs (trzykrotnie po 20 cm3). Warstwę organiczną zobojętnia się solanką wobec papierka wskaźnikowego i osusza bezwodnym siarczanem magnezu. PoExample. In a round bottom flask are placed 1.6 g of (S, E) -3- (2 ', 5'-dimethylphenyl) hex-4-enoic acid, 2.5 g of N-bromosuccinimide (NBS), 50 cm 3 THF and a drop of acetic acid. The whole is stirred on a magnetic stirrer at room temperature, while the course of the reaction is controlled by means of thin-layer chromatography hexane: acetone in the volume ratio of 7: 1. After. When the substrate has completely consumed, it is transferred to a separating funnel, diluted with 30 cm 3 of diethyl ether and washed with saturated NaHCO 3 solution (3 times 20 cm 3 ). The organic layer is neutralized with brine against a indicator paper and dried with anhydrous magnesium sulfate. After
PL 238 122 B1 odsączeniu środka suszącego odparowuje się rozpuszczalnik. Otrzymuje się mieszaninę bromolaktonów, z której metodą chromatografii kolumnowej na żelu krzemionkowym przy zastosowaniu jako eluentu mieszaniny heksan : aceton w stosunku objętościowym 20:1 wydziela się jako jeden z produktów cis -(4 R ,5 R ,6 S)-5-(1-bromoetylo)-4-(2’,5’-dimetylofenylo)-dihydrofuran-2-on w ilości 0,22 g (13% wydajności teoretycznej).After the drying agent was filtered off, the solvent was evaporated. A mixture of bromolactones is obtained, which is separated by column chromatography on silica gel using a hexane: acetone mixture by volume 20: 1 as eluent as one of the products cis - (4R, 5R, 6S) -5- (1 -bromoethyl) -4- (2 ', 5'-dimethylphenyl) -dihydrofuran-2-one in the amount of 0.22 g (13% of theory).
Dane fizyczne i spektroskopowe otrzymanego cis -(4 R ,5 R, 6 S)-5-(1-bromoetylo)-4-2',5'-dimetylofenylo)-dihydrofuran-2-onu są następujące: bezbarwne kryształy, temperatura topnienia 110-115°CThe physical and spectroscopic data of the obtained cis - (4 R, 5 R, 6 S) -5- (1-bromoethyl) -4-2 ', 5'-dimethylphenyl) -dihydrofuran-2-one are as follows: colorless crystals, melting point 110-115 ° C
Rf = 0,47 (heksan/aceton, 3:1), [a]20 = -63,5 (c 0,5; CH2Cl2, ee = 98%).Rf = 0.47 (hexane / acetone, 3: 1). [A] 20 = -63.5 (c 0.5; CH2Cl2, ee = 98%).
1H NMR, δ 1,80 (d, J = 6,6 Hz, 3H, CH3-7), 2,29 (s, 3H, CH3-5'), 2,37 (s, 3H, CH3-2'), 2,21 (dd,1H NMR, δ 1.80 (d, J = 6.6Hz, 3H, CH3-7), 2.29 (s, 3H, CH3-5 '), 2.37 (s, 3H, CH3-2' ), 2.21 (dd,
J = 18,0, 1,8 Hz, 1H, jeden z CH2-3), 3,09 (dd, J =8,0, 9,0 Hz, 1H, jeden z CH2-3), 3,80 (dublet kwartetów,J = 18.0, 1.8 Hz, 1H, one of CH2-3), 3.09 (dd, J = 8.0, 9.0 Hz, 1H, one of CH2-3), 3.80 ( quartet doublet,
J = 9,6, 6,6 Hz, 1H, H-6), 4,11 (ddd, J = 9,0, 6,0, 1,8 Hz, 1H, H-4), 4,75 (dd, J = 9,6, 6,0 Hz. 1 H, H-5),J = 9.6, 6.6 Hz, 1H, H-6), 4.11 (ddd, J = 9.0, 6.0, 1.8 Hz, 1H, H-4), 4.75 ( dd, J = 9.6, 6.0 Hz. 1H, H-5),
6,86 (s, 1H, H-6'), 7,00 (m, 1H, H-4'), 7,06 (d, J = 7,8 Hz, 1H, H-3');6.86 (s, 1H, H-6 '), 7.00 (m, 1H, H-4'), 7.06 (d, J = 7.8Hz, 1H, H-3 ');
13C NMR: δ 19,87 (CH3-2'), 21,18 (CH3-5'), 23,37 (C-7), 38,41 (C-3), 38,53 (C4), 45,29 (C-6), 86,76 (C-5), 126,45 (C-61), 128,47 (C4'), 130,91 (G-3’), 133,29 (C-2'), 136,11 (C-5'), 136,42 (C-1'), 13 C NMR: δ 19.87 (CH3-2 '), 21.18 (CH3-5'), 23.37 (C-7), 38.41 (C-3), 38.53 (C4), 45.29 (C-6), 86.76 (C-5), 126.45 (C-6 1 ), 128.47 (C4 '), 130.91 (G-3'), 133.29 ( C-2 '), 136.11 (C-5'), 136.42 (C-1 '),
176,41 (C-2);176.41 (C-2);
IR (cm-1): 1774 (s), 1506 (w), 1185 (s), 1147 (s), 989 (m), 823 (m), 629 (m).IR (cm -1 ): 1774 (s), 1506 (w), 1185 (s), 1147 (s), 989 (m), 823 (m), 629 (m).
Claims (4)
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