CN113896755B - Synthesis method of 2-deoxyglycoxyglycoside and application of 2-deoxyglycoxyglycoside in pharmacy - Google Patents
Synthesis method of 2-deoxyglycoxyglycoside and application of 2-deoxyglycoxyglycoside in pharmacy Download PDFInfo
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Abstract
The invention provides a method for synthesizing 2-deoxyglycoxyglycoside, which comprises the steps ofOAdding the carbonate galactose alkene sugar, the sugar acceptor and the catalyst into an organic solvent, stirring at room temperature, and detecting the reaction progress by TLC when 3,4-OAfter the complete disappearance of the carbonate galactoalkene sugar raw material, the reaction is stopped, the organic phase is extracted and collected, the solvent is removed by reduced pressure distillation to obtain a crude product, and then the petroleum ether/ethyl acetate solution is used as a mobile phase for column chromatography to obtain the 2-deoxyglucoside. Alpha-diacetone D-galactose-3, 4-O-2-deoxyglycoside and alpha-L-menthol-3, 4-)O-2-deoxyglycosides show a remarkable inhibitory effect on glucosidase, whose IC on glucosidase was calculated 50 Values of 121.14 respectivelyμM and 54.64μM。
Description
Technical Field
The invention relates to a method for synthesizing 2-deoxyglycoxyglycoside and application thereof in the pharmaceutical field.
Background
Deoxysugars are fundamental structural components constituting various bioactive natural products, and many bioactive compounds, especially antitumor antibiotics, such as anthracyclines, aureomycins, protomycins, an Gehuan, contain one or more 2-deoxyglycosides in their backbone. As an important subclass of deoxysugars, 2-deoxyglycosides lack a directing group at C-2 that controls the anomeric selectivity, which makes their stereoselective synthesis challenging. Despite the difficulty and weight, efforts have been made to develop stereoselective glycosylation methods to construct 2-deoxyglycosidic linkages.
Stereoselective construction of 2-deoxy sugars has been achieved through indirect and direct synthetic strategies. In indirect synthesis, a temporary directing group is usually pre-installed at C-2 to help control the anomeric selectivity in glycosylation, which then needs to be removed.However, pre-installation and removal of these temporary directing groups typically require additional steps, resulting in reduced efficiency of the indirect synthesis process. On the other hand, direct synthesis of 2-deoxy sugars is considered more "direct" and "atom economical", with higher synthesis efficiency, but stereoselective control is generally more challenging due to the absence of temporary directing groups on C-2. In fact, the synthesis of 2-deoxyglycosides using direct methods often results in a mixture of α -and β -anomers. Stereochemical results may depend on many factors including the stereochemistry of the glycosyl donor, protecting group, leaving group, catalyst, solvent, additive, and the relative reactivity of the glycosyl acceptor. The present invention is directed to finding a low toxicity and low cost catalyst and excellent green solvent, end use Fe (OTf) 3 The mild catalyst activates the sugar ring in the presence of the green solvent DMC and prepares the corresponding 2-deoxyglycoxyglycoside with high selectivity.
Disclosure of Invention
Aiming at the technical problems, the invention provides a synthetic method of 2-deoxyglycoxyglycoside, which comprises the following steps: adding 3, 4-O-carbonate galactose alkene sugar, a sugar acceptor and a catalyst into an organic solvent, stirring at room temperature, detecting the reaction progress by TLC, stopping the reaction after the 3, 4-O-carbonate galactose alkene sugar material completely disappears, extracting and collecting an organic phase, distilling under reduced pressure to remove the solvent to obtain a crude product, and performing column chromatography by using petroleum ether/ethyl acetate solution as a mobile phase to obtain the 2-deoxyglucoside.
The sugar receptor comprises natural product molecules such as 2-hydroxy pyranose, 3-hydroxy pyranose, 4-hydroxy pyranose, 6-hydroxy pyranose, 3-hydroxy furanose, 5-hydroxy furanose, monohydroxy terpenes, steroids, flavonoids and the like.
The sugar receptor comprises diacetone D-glucose, diacetone D-galactose, glucose with hydroxyl at different positions, glucosamine, mannose, fucose, diosgenin, cholesterol, D-menthol, L-menthol, etc.
The catalyst comprises Fe (OTf) 3 、Hg(OTf) 2 Any one of AgOTf.
The molar ratio of 3, 4-O-carbonate galactose alkene sugar, sugar acceptor and catalyst is 1:1.1-1.5:0.01-0.15.
The organic solvent comprises any one of DCM, DEC, toluene.
The invention also provides an application of the prepared 2-deoxyglucose oxy-glycoside in preparing medicines for treating human breast cancer. The human breast cancer cell is MCF-7.
Or the application of the prepared 2-deoxyglucosyloxy glycoside in preparing medicaments for inhibiting glucosidase.
The product synthesized by the invention is subjected to preliminary biological activity research. Human breast cancer cells (MCF-7) were used to evaluate the antiproliferative biological activity of the compounds. Fortunately, the compound α -diosgenin-3, 4-O-2-deoxyglycoside showed significant inhibition of human breast cancer cells. Calculate its IC for human breast cancer cells 50 The value is 51.324 mug/L, which shows that the compound has a certain anti-tumor activity. In addition, glucosidase was used to evaluate the inhibitory activity of the compounds. Fortunately, the compounds α -diacetone D-galactose-3, 4-O-2-deoxyglycoside and α -L-menthol-3, 4-O-2-deoxyglycoside showed a significant inhibitory effect on glucosidase, whose IC on glucosidase was calculated 50 The values were 121.14. Mu.M and 54.64. Mu.M, respectively.
Drawings
FIG. 1 shows a diagram of α -diacetone D-galactose-3, 4-O-2-deoxyglycoside 1 H NMR。
FIG. 2 shows a diagram of α -diacetone D-galactose-3, 4-O-2-deoxyglycoside 13 C NMR。
FIG. 3 is a diagram of alpha-diosgenin-3, 4-O-2-deoxyglycoside 1 H NMR。
FIG. 4 shows a view of alpha-diosgenin-3, 4-O-2-deoxyglycoside 13 C NMR。
Detailed Description
The experimental reagents used in this example include the following:
iron triflate (microphone), methylene chloride (analytically pure, tianjin, miou chemical reagent Co., ltd.), petroleum ether (boiling range 60-90 ℃ C., tianjin, heng Xingxingxiao chemical reagent Co., ltd.), ethyl acetate (analytically pure, tianjin, miou chemical reagent Co., ltd.), anhydrous sodium sulfate (analytically pure, national drug group chemical reagent Co., ltd.), deuterated chloroform (deuterium atom content 99.8%, TMS content 0.03% V/V,10 x 0.5 mL/box, switzerland ARMAR Co.); nuclear magnetic resonance tube (5 mm 100/pk2ST500-8, norell Co., U.S.A.).
The experimental apparatus used in this example includes the following:
ZXZ-4 rotary vane vacuum pump (Tanshi vacuum apparatus Co., ltd., lin-sea), DZF-6020 vacuum drying oven (Shanghai New Miao medical instruments Co., ltd.), SHB-IIIA circulating water type multipurpose vacuum pump (Shanghai Yukang scientific teaching Instrument Co., ltd.), CL-4 type flat magnetic stirrer (Zheng, great wall Co., ltd.), EYELA SB-1100 rotary evaporator (Shanghai Ailang instruments Co., ltd.), FA2104B analytical balance (Shanghai plain scientific instrument limited), XRC-1 micro-melting point tester (university of Sichuan instrumentation), DF-101S heat collection type constant temperature heating magnetic stirrer (consolidated quartz and quartz pre-bloom instrumentation), GZX-9240MBE digital display blast drying box (Shanghai bosin real company medical equipment factory), ZF-6 three-purpose ultraviolet analyzer (Shanghai jiaweng scientific limited), ultrashed 400MHz Plus nuclear magnetic resonance instrument (Bruker company of switzerland).
Example 1
The alpha-diacetone D-galactose-3, 4-O-2-deoxyglucoside is prepared by taking 3, 4-O-carbonate galactose olefine sugar as a raw material, and the technical route is as follows:
3, 4-O-Carbonic acid ester galactose alkene sugar 1 (0.1 mmol), sugar acceptor (diacetone D-galactose) (0.12 mmol) and ferric triflate (Fe (OTf) 3 0.01 mmol) was added to 2mL of dimethyl carbonate. Stirring at room temperature, TLC detecting reaction progress, terminating reaction after complete disappearance of allyl feed, extracting and collecting organic phase, vacuum distilling to remove solvent to obtain crude product, column chromatography with petroleum ether/ethyl acetate solution as mobile phase to obtain α -diacetone D-galactose-3, 4-O-2-deoxyglycoside (yield 89%), andthe compound has good glucosidase inhibitory activity through test.
Aiming at the process, the invention takes carbonate galactose alkene sugar as an example, adjusts and optimizes the catalyst, the ligand, the alkali and the solvent, and the condition is selected as follows:
note that all experiments employed 0.1mmol of carbonate galactose and 0.12mmol of diacetone-D-galactose, 10mol% Fe catalyst in 2mL of solvent at room temperature with stirring; isolation yield; stereoselectivity was measured by nuclear magnetic resonance hydrogen spectroscopy > =30:1.
The technical scheme of the invention screens and optimizes the reaction conditions. The catalyst was first screened in DCM as solvent (entries 1-5). It was found that the reaction time was longer when AgOTf was used as catalyst (entrie 1). Then using Zn (OTf) 2 And Ni (OTf) 2 The catalyst was tested (entries 2-3) and the results showed poor or even no reaction. Then Hg (OTf) 2 Experiments were performed (entrie 4), the reaction was completed quickly and the yield was higher, but with Hg (OTf) in mind 2 The toxicity is high, and other catalysts are screened. When Fe (OTf) 3 With the catalyst, the reaction was completed quickly and the yield was higher (entrie 5), so Fe (OTf) was finally taken up 3 The optimal catalyst is determined. Next, the reaction solvent was optimized (entries 6-8), and the optimization result showed that tolene as solvent could catalyze the reaction, but the best reaction was still DCM. Solvent optimisation again attempted to be drawn toward green solvent, and after screening to DEC (entries 9), good green solvent DMC (entries 10) was finally screened.
Results of the review experiments, the optimal reaction conditions for obtaining galactose 2-deoxyglycoside are as in Fe (OTf) 3 DMC as catalyst when used as solventThe reaction effect is best.
Example 2
The method and the process conditions are the same as those in the example 1 (namely, the example with the highest yield), and the alpha-diosgenin-3, 4-O-2-deoxyglucoside is prepared by taking 3, 4-O-carbonate galactose glycal as a raw material, and the technical route is as follows:
3, 4-O-Carbonic acid galacto-olefine sugar 1 (0.1 mmol), sugar acceptor (dioscin) (0.12 mmol) and ferric triflate (Fe (OTf) 3 0.01 mmol) was added to 2mL of dimethyl carbonate. Stirring at room temperature, detecting the reaction progress by TLC, stopping the reaction after the alkene sugar material completely disappears, extracting and collecting an organic phase, decompressing and distilling to remove a solvent to obtain a crude product, and then adopting petroleum ether/ethyl acetate solution as a mobile phase to carry out column chromatography to obtain the alpha-diosgenin-3, 4-O-2-deoxyglucoside (the yield is 80%), wherein the compound has good activity of resisting human breast cancer cells through test.
Using the process and conditions of example 1 as those of the following examples, the synthetic preparation of different substrates was screened, the substrate ranges were as follows:
preparation of 2-deoxyglycooxy-glycosides from disaccharide substrates
Preparation of 2-deoxyglycoxyglycoside from natural product substrate
Preparation of 2-deoxyglycoxyglycoside from different sugar substrates
Nuclear magnetic resonance spectrum data
(3aR,4R,6S,7aR)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-6-(((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methoxy)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-2-one
1 H NMR(400MHz,CDCl 3 )δ7.68–7.64(m,4H),7.45–7.38(m,6H),5.45(d,J＝5.0Hz,1H),5.05–4.99(m,2H),4.89(dd,J＝8.5,1.7Hz,1H),4.51(dd,J＝7.9,2.5Hz,1H),4.28(dd,J＝5.0,2.5Hz,1H),4.11(dd,J＝7.8,1.9Hz,1H),4.07–4.02(m,1H),3.98–3.94(m,1H),3.85–3.66(m,4H),2.47(ddd,J＝15.8,5.7,3.9Hz,1H),1.89(ddd,J＝15.8,6.8,3.4Hz,1H),1.42(d,J＝15.1Hz,6H),1.31(d,J＝6.0Hz,6H),1.06(s,9H).
13 C NMR(100MHz,CDCl 3 )δ154.5,135.7,135.6,133.2,132.9,130.0,123.0,128.0,128.0,109.6,108.8,96.5,95.4,73.4,72.2,71.1,70.8,70.6,67.8,66.6,65.9,61.6,29.5,26.9,26.1,26.1,25.0,24.7,19.4.
(3aR,4R,6S,7aR)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-6-(((4S,5'R,6aR,6bS,8aS,8bS,9S,10R,11aR,12aS,12bS)-5',6a,8a,9-tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-2-one
1 H NMR(400MHz,CDCl 3 )δ7.69–7.62(m,4H),7.45–7.36(m,6H),5.20–5.09(m,2H),5.03–4.97(m,1H),4.84(dd,J＝8.4,1.7Hz,1H),4.44–4.36(m,1H),4.00(ddd,J＝7.7,6.1,1.7Hz,1H),3.85(dd,J＝10.2,7.5Hz,1H),3.77(dd,J＝10.2,6.2Hz,1H),3.53–3.43(m,2H),3.37(t,J＝10.9Hz,1H),2.41(ddd,J＝15.7,5.7,4.0Hz,1H),2.25–2.14(m,2H),2.01–1.89(m,2H),1.89–1.72(m,6H),1.72–1.65(m,3H),1.64–1.55(m,4H),1.52–1.36(m,5H),1.31–1.23(m,1H),1.17(dd,J＝12.6,4.8Hz,1H),1.05(s,9H),1.00–0.95(m,6H),0.79(d,J＝6.5Hz,6H).
13 C NMR(100MHz,CDCl 3 )δ154.8,140.7,136.0,135.9,133.5,133.2,130.4,130.3,128.3,128.3,122.2,109.7,93.2,81.3,76.8,73.9,72.7,68.1,67.3,62.5,62.1,56.9,50.6,42.0,40.7,40.7,40.2,37.3,37.2,32.4,32.3,31.8,30.7,30.2,29.2,28.1,27.3,21.2,19.8,19.7,17.6,16.8,15.0.
Materials and methods for biological Activity evaluation
Antitumor cytotoxicity experiment (MCF-7)
Human breast cancer cells (MCF-7, from cell bank of the China academy of sciences of the type culture Collection, shanghai cell biology institute, china academy of sciences) were seeded in 96-cell plates (100. Mu.L) with a single well (1.0X10 5 Individual cells/well), 10% foetal calf serum and 100 units/ml penicillin in Dulbecco's modified medium with a humidity of 5% CO 2 An atmosphere. Cell lines were exposed to different concentrations of drug (0, 15, 30, 45, 60, 75 μg/mL) for 48h and a blank group was set without drug. MTT (50. Mu.L of 5mg/mL phosphate buffered saline) was added to each well and the cell line was cultured in a carbon dioxide incubator at 37℃for 5 hours. After removal of the medium, MTT-methyl formed using metabolically living cells was dissolved in 200. Mu.L of dimethyl sulfoxide, and absorbance was measured in a plate reader at 490 nm. Survival (%) was calculated using the following formula: number of living cells (cells without dye)/total number. The results show that the IC of the alpha-diosgenin-3, 4-O-2-deoxyglucoside human breast cancer cells 50 The value is 51.324 mug/L, which shows that the compound has a certain anti-tumor activity.
Alpha-glucosidase inhibitory Activity assay
Alpha-glucosidase inhibitory Activity in PBS buffer (0.1M KH 2 PO 4 -K 2 HPO 4 pH 6.8), p-nitrophenyl-alpha-D-glucoside (PNPG) is used as a reaction substrate. The alpha-glucosidase was derived from heterologous expression of the human alpha-glucosidase gene in yeast Saccharomyces cerevisiae. mu.L of the sample solution to be tested(DMSO-dissolved), 58. Mu.L of PBS buffer, 30. Mu.L of alpha-glucosidase (0.2U/mL) diluted with 0.01M PBS, and 30. Mu.L of PNPG (1.25 mM) were added to a 96-well plate and reacted for 15min, and UV absorbance at 405nm was measured with a microplate reader. The positive medicine is acarbose and 1-deoxynojirimycin, and the negative control is DMSO. The compounds α -diacetone D-galactose-3, 4-O-2-deoxyglycoside and α -L-menthol-3, 4-O-2-deoxyglycoside showed a remarkable inhibitory effect on glucosidase, and IC for glucosidase was calculated 50 The values were 121.14. Mu.M and 54.64. Mu.M, respectively.
Claims (3)
1. The synthesis method of the 2-deoxyglycoxyglycoside is characterized by comprising the following steps:
3,4-OAdding the carbonate galactose alkene sugar, the sugar acceptor and the catalyst into an organic solvent, stirring at room temperature, and detecting the reaction progress by TLC when 3,4-OTerminating the reaction after the complete disappearance of the carbonate galactose alkene sugar raw material, extracting and collecting an organic phase, decompressing and distilling to remove a solvent to obtain a crude product, and then carrying out column chromatography by adopting petroleum ether/ethyl acetate solution as a mobile phase to obtain 2-deoxyglucoside;
the sugar acceptor is diacetone D-galactose or L-menthol;
the catalyst is selected from Fe (OTf) 3 ，
The organic solvent is selected from any one of DCM, toluene, DEC, DMC.
2. The method for synthesizing 2-deoxyglycoxyglycoside according to claim 1, wherein 3,4-OThe molar ratio of carbonate galactose alkene sugar, sugar acceptor and catalyst is 1:1.1-1.5:0.01-0.15.
3. Use of a 2-deoxyglycoxyglycoside prepared according to claim 1 or 2 for the preparation of a medicament for inhibiting glucosidase, said prepared 2-deoxyglycoxyglycoside being selected from the group consisting of alpha-diacetone D-galactose-3, 4-O2-deoxyglycoside or alpha-L-menthol-3, 4-)O-2-deoxyglycoside.
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