CN102241710A - Salidroside analogues as well as preparation method and application thereof - Google Patents

Salidroside analogues as well as preparation method and application thereof Download PDF

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CN102241710A
CN102241710A CN2011101006675A CN201110100667A CN102241710A CN 102241710 A CN102241710 A CN 102241710A CN 2011101006675 A CN2011101006675 A CN 2011101006675A CN 201110100667 A CN201110100667 A CN 201110100667A CN 102241710 A CN102241710 A CN 102241710A
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glucopyranoside
hydroxyl
styroyl
phenmethyl
galactopyranoside
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杨宇民
顾晓松
丁斐
刘梅
郭益冰
刘炎
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Nantong University
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Nantong University
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Abstract

The invention discloses salidroside analogues as well as a preparation method and application thereof. The preparation method comprises the steps such as preparing an intermediate, namely acetyl glucoside, preparing the salidroside analogues and other steps. The obtained products can be used for low-sugar low-serum damage protection of PC12 cells, and the treatment of central nervous and peripheral nervous injury and wasting diseases. In the preparation method, when an aromatic ring contains a hydroxyl group, an acetyl group is used for protecting the hydroxyl group, so that the acetyl group is conveniently removed at the same time of the removal of the acetyl group on a sugar ring, thus avoiding the use of allyl and benzyl protection, shortening the reaction process and lowering the cost; the used solvent is a low-residue aprotic mixed solvent of dichloromethane and diethyl ether, and the glucoside is formed after reacting is performed at room temperature for 10 hours, thus avoiding the use of other more toxic solvents; by using a common inorganic reagent, namely potassium carbonate, the acetyl group is removed, and during column chromatography, dichloromethane is used for substituting for chloroform, thus contributing to the health of operators; and trace iodine is used as a catalyst, anhydrous calcium sulfate is used as a dewatering agent and a powdery 4-angstrom molecular sieve is added.

Description

Rhodioside analogue and its production and use
Technical field
The present invention relates to a kind of rhodioside analogue and its production and use.
Background technology
Rhodioside (salidroside) is the main effective constituent of Rosales Crassulaceae (Crassulaceae) rhodiola (Rhodiola) plant, and obtain natural mainly the separation from the plateau plant Root of Kirilow Rhodiola of the laudatory title of enjoying " plateau genseng ", " arctic rose ".Rhodioside, English by name Salidroside, systematic naming method are 2-(4-leptodactyline)-β-D-glucoside (2-(4-hydroxy) phenethyl-β-D-glucoside).Rhodioside can nervous system regulation, have eliminate depressed, increase work efficiency, effects such as hypoxia tolerance, radioprotective and Ginseng Extract, and can prevent altitude sickness and improve sleep.As a kind of traditional Chinese medicine with " adaptogen " effect, Root of Kirilow Rhodiola by many under particular surroundings the active personnel, as frogman, spacefarer, pilot and mountaineer etc., be used for the ability of enhancing body opposing severe environment.
Root of Kirilow Rhodiola is the main plant of extracting rhodioside, but because it grows in the highland and severe cold areas of ecology fragility, regenerative power is relatively poor, naturally regeneration slow (generally needing 7-8 to adopt), and it is quite big to produce required herb resource consumption, the wild resource reserves reduce day by day, and resource exhaustion will appear in the aggravation along with exploitation.The extraction of natural salidroside not only needs complicated extraction process, and general extraction yield can only reach the 0.4-0.8% of plant dry weight.Therefore developing alternate resources seems very important, is the important means of development alternate resources and utilize biotechnology and chemical synthesis process.And, because rhodioside is difficult by hemato encephalic barrier, in vivo the transformation period very short, therefore seek the preparation of its analog, expection is sought to have bioactive preferably compound and seems particularly important.
In recent years, pharmacological activity for rhodioside has carried out extensive studies, and it is less for the study on the synthesis of its analogue, reported mainly based on the instability of oxygen glycosides, change into sulphur glycosides and carbon glycosides, and grayanoside A and syringalide B have been synthesized in 4,6 modifications that the simulation natural product carries out.
Summary of the invention
The object of the present invention is to provide a kind of rhodioside analogue and its production and use.
Technical solution of the present invention is:
A kind of rhodioside analogue is characterized in that: chemical structural formula is:
Figure BDA0000056567740000021
R wherein 1The expression glycosyl donor is glucose, semi-lactosi, lactose, wood sugar, (N-acetyl) glucosamine, seminose or pectinose; R 2The expression phenyl ring is the substituting group on the coordination not, can be connected the optional position of phenyl ring, R 2Be specially: H, OH, Cl, Br, F, OCH 3Or OEt, but do not comprise R 1During for D (+) glucose, R 2During for hydroxyl, hydroxyl OH is connected the situation of 4 of phenyl ring; X=1-3.
Described rhodioside analogue; for: 2-(4-hydroxyl) styroyl-β-D-galactopyranoside; 1-(4-hydroxyl) phenmethyl-β-D-glucopyranoside; 1-(4-hydroxyl) phenmethyl-β-D-galactopyranoside; 1-phenmethyl-β-D-glucopyranoside; 1-phenmethyl-β-D-galactopyranoside; 2-styroyl-β-D-glucopyranoside; 2-styroyl-β-D-galactopyranoside; 1-(4-chlorine) phenmethyl-β-D-glucopyranoside; 1-(4-chlorine) phenmethyl-β-D-galactopyranoside; 1-(2; the 4-dichloro) phenmethyl-β-D-glucopyranoside; 1-(2; the 4-dichloro) phenmethyl-β-D-galactopyranoside; 1-(2-methoxyl group) phenmethyl-β-D-glucopyranoside; 1-(2-methoxyl group) phenmethyl-β-D-galactopyranoside; 1-(4-methoxyl group) phenmethyl-β-D-glucopyranoside; 1-(4-methoxyl group) phenmethyl-β-D-galactopyranoside; 1-(3; the 4-dimethoxy) phenmethyl-β-D-glucopyranoside; 1-(3; the 4-dimethoxy) phenmethyl-β-D-galactopyranoside; 1-(3; the 5-dimethoxy) phenmethyl-β-D-glucopyranoside; 1-(3; the 5-dimethoxy) phenmethyl-β-D-galactopyranoside; 1-(3; 4; the 5-trimethoxy) phenmethyl-β-D-glucopyranoside; 1-(3; 4; the 5-trimethoxy) phenmethyl-β-D-galactopyranoside; 2-(3; 4; the 5-trimethoxy) styroyl-β-D-glucopyranoside; 2-(3; 4; the 5-trimethoxy) styroyl-β-D-galactopyranoside; 3-(3; 4; the 5-trimethoxy) hydrocinnamyl-β-D-glucopyranoside; 3-(3; 4; the 5-trimethoxy) hydrocinnamyl-β-D-galactopyranoside; 2-(3; 4; the 5-trihydroxy-) styroyl-β-D glucopyranoside; 2-(3; 4; the 5-trihydroxy-) styroyl-β-D galactopyranoside; 3-(3; 4; the 5-trihydroxy-) hydrocinnamyl-β-D glucopyranoside; 3-(3,4, the 5-trihydroxy-) hydrocinnamyl-β-D galactopyranoside; 1-(2; 3; 4,5,6-five fluorine) phenmethyl-β-D-glucopyranoside; 1-(2; 3; 4,5,6-five fluorine) phenmethyl-β-D-galactopyranoside; 2-(2; 3; 4,5,6-five fluorine) styroyl-β-D-glucopyranoside; 2-(2; 3; 4,5,6-five fluorine) styroyl-β-D-galactopyranoside; 3-(2; 3; 4,5,6-five fluorine) hydrocinnamyl-β-D-glucopyranoside; 3-(2; 3; 4,5,6-five fluorine) hydrocinnamyl-β-D-galactopyranoside; 1-(2; 3; 5,6-tetrafluoro-4-hydroxyl) phenmethyl-β-D-glucopyranoside; 1-(2,3; 5; 6-tetrafluoro-4-hydroxyl) phenmethyl-β-D-galactopyranoside; 2-(2,3,5; 6-tetrafluoro-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(2; 3,5,6-tetrafluoro-4-hydroxyl) styroyl-β-D-galactopyranoside; 3-(2; 3; 5,6-tetrafluoro-4-hydroxyl) hydrocinnamyl-β-D-glucopyranoside; 3-(2,3; 5; 6-tetrafluoro-4-hydroxyl) hydrocinnamyl-β-D-galactopyranoside; 2-(3-methoxyl group-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3-methoxyl group-4-hydroxyl) styroyl-β-D-galactopyranoside; 2-(3,5-dimethoxy-4 '-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3,5-dimethoxy-4 '-hydroxyl) styroyl-β-D-galactopyranoside; 2-(3-bromo-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3-bromo-4-hydroxyl) styroyl-β-D-galactopyranoside; 2-(3; 5-two bromo-4-hydroxyls) styroyl-β-D-glucopyranoside; 2-(3; 5-two bromo-4-hydroxyls) styroyl-β-D-galactopyranoside; 2-(3-oxyethyl group-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3-oxyethyl group-4-hydroxyl) styroyl-β-D-galactopyranoside; 1-(3-ethanoyl-4-hydroxyl) phenmethyl-β-D-glucopyranoside; 1-(3-ethanoyl-4-hydroxyl) phenmethyl-β-D-galactopyranoside; 2-(3-ethanoyl-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3-ethanoyl-4-hydroxyl) styroyl-β-D-galactopyranoside; 3-(3-ethanoyl-4-hydroxyl) hydrocinnamyl-β-D-glucopyranoside; 1-(4-hydroxyl) phenmethyl-2-kharophen β-D-glucopyranoside; 2-(4-hydroxyl) styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 3-(4-hydroxyl) hydrocinnamyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 1-(3-hydroxyl) phenmethyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 2-(3-hydroxyl) styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 3-(3-hydroxyl) hydrocinnamyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 2-(4-methoxyl group) styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 3-(4-methoxyl group) hydrocinnamyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 1-(3, the 5-dimethoxy) phenmethyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 2-(3, the 5-dimethoxy) styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 1-phenmethyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 2-styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; in 2-(4-hydroxyl) styroyl-2-amino-beta--D-glucopyranoside any one.
A kind of preparation method of rhodioside analogue is characterized in that: concrete steps are:
(1) preparation of intermediate-acetyl glucosides
A: with radicals R 2The pure and mild required glycosyl donor R that replaces 1Acetyl-alpha-bromo-derivative be raw material, be catalyzer with silver carbonate, iodine, anhydrous calciumsulphate is a water-removal agent,
Figure BDA0000056567740000051
Molecular sieve is used to adsorb small molecules hydrogen bromide, water, under lucifuge and the exsiccant protection of inert gas, is dissolved in the corresponding non-proton organic solvent, reacts under 15-45 ℃, obtains intermediate acetyl glucose glycosides or galactoside;
Or B: with radicals R 2The pure and mild required glycosyl donor R that replaces 1Acetyl alpha-chloro thing be raw material, with zinc chloride and 4,4 '-the dimethoxytrityl methyl chloride is as catalyzer, is dissolved in corresponding non-proton organic solvent and reacts under 15-45 ℃, obtains intermediate: the acetylize glucosaminide;
(2) rhodioside analogue preparation
The gained intermediate is taken off the acetyl protection base in containing the reagent of strong alkaline substance; Solvent is chosen as methyl alcohol, ethanol, tetrahydrofuran (THF) or ether, and the reaction times is 2-6h, and temperature of reaction is 10-40 ℃; The gained crude product is obtained the rhodioside analogue with high-efficient liquid phase technique, column chromatography or solvent recrystallization method purifying, and (developping agent is a methyl alcohol: methylene dichloride=1: 6-1: 9) in preferred column chromatography optimization.Promptly obtain needed target compound-rhodioside and analogue thereof behind the purifying.
Non-proton organic solvent is benzene, Nitromethane 99Min., tetrahydrofuran (THF), 1 described in step (1) A, one or more mixed solvents in 2-glycol dimethyl ether, methylene dichloride, the ether.
Non-proton organic solvent is a tetrahydrofuran (THF), 1 described in step (1) B, one or several mixed solvents in 2-glycol dimethyl ether, methylene dichloride, the ether.
Strong alkaline substance described in the step (2) is sodium methylate, sodium ethylate, Anhydrous potassium carbonate, sodium hydride or sodium hydroxide.
A kind of described rhodioside analogue is used for the application of the medicine of the low serum injury protection of PC12 cell low sugar, treatment nervus centralis and peripheral nerve injury, wasting diseases in preparation.
Described wasting diseases is tumour, like disease and disease of immune system now.
The inventive method prepares the improvements of glucosides: produce when 1) aromatic ring contains phenolic hydroxyl group and protect with ethanoyl, be convenient to remove simultaneously when removing sugar ring ethanoyl, avoid using allyl group, benzyl protection, shorten reaction scheme, reduce cost; 2) solvent for use is the methylene dichloride of low residue and the mixing non-protonic solvent of ether, and room temperature reaction 10h becomes glycosides, avoids the solvent that uses other toxicity stronger.Remove ethanoyl by this common inorganic reagent of salt of wormwood, cross post and use methylene dichloride to replace chloroform, help operator's health.3) used micro iodine as catalyzer, reached anhydrous calciumsulphate as water-removal agent, and added Powdered Molecular sieve.
The present invention as glycosyl donor, has prepared rhodioside analogue glucosides with acetylglucosamine first.The present invention has used the aromatic alcohol of more different substituents and different glycosyl donors to synthesize the rhodioside analogue.
The present invention is synthetic rhodioside and analogue thereof, through common materialization data and infrared, and nuclear-magnetism, ultimate analysis detects identifies that chemical structure is seen as following table 1.
Table 1 is synthetic rhodioside and analogue thereof
Figure BDA0000056567740000062
Figure BDA0000056567740000071
Figure BDA0000056567740000081
Adopt mtt assay, listed rhodioside and part analogue thereof are tested for the effect of vigor of the PC12 cell of the low serum damage of low sugar in the his-and-hers watches 1, concrete grammar as follows:
Instrument: full-automatic microplate reader (Bio-Tek company), carbon dioxide cell incubator (NAPCO company), inverted microscope (Leica company)
1. the low serum modelling of soup preparation and low sugar
Accurately take by weighing synthetic rhodioside of institute and part analogue and be dissolved in the PBS buffered soln, the mother liquor that is prepared into 10mmol/L is standby; Use with DMEM high glucose medium and sugar-free culture-medium dilution by a certain percentage before the use, final concentration is 60 μ mol/L, 300 μ mol/L, 1000 μ mol/L.Cell is handled and grouping: get the PC12 cell that is in logarithmic phase in the culture dish, it is about 1-5 * 10 that cell density is adjusted in centrifugal back 4/ ml is inoculated in 96 well culture plates, every hole 100 μ l.Experiment is grouped as follows: low sugar is hanged down serum damage group, cultivates 24h in the low blood serum medium of low sugar; The basic, normal, high dosage group of glucosides is 60 μ mol/L with final concentration respectively before the low serum damage of low sugar, 300 μ mol/L, and 1000 μ mol/L pretreatment cell 24h, and in the low serum treating processes of low sugar, keep original drug level; The normal control group is not promptly carried out the low serum damage of low sugar.
2.MTT measure
Stop cultivating behind the low serum damage of the low sugar 24h, every hole adds 20 μ l MTT stostes, and 37 ℃ are continued to cultivate 4h, and sucking-off stoste adds DMSO, vibration 15min.Is to measure its optical density value under the 570nm with enzyme-linked immunosorbent assay instrument at wavelength.Each experimental group is established 8 multiple holes, and experiment repeats 3 times.
The PC12 cell is hanged down the protection measurement result of serum damage in low sugar: with cultivation group fully is 100, the results are shown in Table 2.
Table 2 compound is to the provide protection of the low serum damage of PC12 cell low sugar
Figure BDA0000056567740000091
Figure BDA0000056567740000111
Annotate: compound number is corresponding with table 1 in the table
As can be seen from Table 2; rhodioside and analogue thereof all have the effect of the low serum damage of protection low sugar PC12 cell: middle concentration compound 19 and 20 effects of low concentration compound are stronger, and acetylamino sugars is also better as the rhodioside analogue effect of glycosyl donor.Thereby rhodioside of the present invention and analogue thereof can be used for the low serum damage of antagonism PC12 cell low sugar.
Embodiment
Now in conjunction with example, the preparation method of The compounds of this invention is done detailed description.
The preparation of embodiment 1:1-(4-hydroxyl) styroyl-β-D-glucopyranoside (rhodioside, compound number 1).
The mixed solvent 15ml (2: 1) that in the 50ml round-bottomed flask, adds anhydrous methylene chloride and ether; tyrosol 0.55g (4.0mmol); silver carbonate 1.2g (4.5mmol), and the iodine trace (0.1～0.5ml), Powdered molecular sieve 2g; lucifuge stirs 30min under the nitrogen protection; add 2,3,4; 6-four-O-ethanoyl-α-D-bromo Glucopyranose 1.95g (5mmol), room temperature reaction 10h.Filter, remove solvent under reduced pressure, get thick colourless syrup, add the methanol solution 15ml that is dissolved with salt of wormwood, room temperature reaction 6h filters, acidic resins neutralization, column chromatography for separation, methyl alcohol: methylene dichloride=1: 5, obtain the white solid 0.98g of compound 1, mp159-160 ℃, yield 81.6%.
The preparation of embodiment 2:1-(4-chlorine) phenmethyl-β-D-galactopyranoside (compound 10).
The mixed solvent 15ml (2: 1) that in the 50ml round-bottomed flask, adds anhydrous methylene chloride and ether; 4-chlorobenzene methanol 0.57g (4mmol); silver carbonate 1.2g (4.5mmol), and the iodine trace (0.1～0.5ml), Powdered molecular sieve 2g; lucifuge stirs 30min under the nitrogen protection; add 2,3,4; 6-four-O-ethanoyl-α-D-bromo Glucopyranose 1.95g (5mmol), room temperature reaction 10h.Filter, remove solvent under reduced pressure, get thick colourless syrup, add the methanol solution 15ml that is dissolved with salt of wormwood, room temperature reaction 6h, filter acidic resins neutralization, column chromatography for separation, methyl alcohol: methylene dichloride=1: 6, obtain little yellow solid 0.95g of compound 10, mp 138-140 ℃, yield 78.1%.
The preparation of embodiment 3:1-(3, the 5-dimethoxy) phenmethyl-β-D-glucopyranoside (compound 19).
The mixed solvent 15ml (2: 1) that in the 50ml round-bottomed flask, adds anhydrous methylene chloride and ether; 3,5-3,5-dimethoxybenzoic alcohol 0.67g (4mmol), silver carbonate 1.2g (4.5mmol); iodine trace (0.1～0.5ml); Powdered molecular sieve 2g, lucifuge stirs 30min under the nitrogen protection, adds 2; 3; 4,6-four-O-ethanoyl-α-D-bromo Glucopyranose 1.95g (5mmol), room temperature reaction 10h.Filter, remove solvent under reduced pressure, get thick colourless syrup, add the methanol solution 15ml that is dissolved with salt of wormwood, room temperature reaction 6h filters, acidic resins neutralization, column chromatography for separation, methyl alcohol: methylene dichloride=1: 4, obtain the white solid 1.08g of compound 19,146-148 ℃, yield 81.8%.
The preparation of embodiment 4:1-phenmethyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside (compound 68).
In the 50ml round-bottomed flask, add anhydrous methylene chloride 15ml; with zinc chloride 0.41g (3mmol) and 4; 4 '-dimethoxytrityl methyl chloride (1.03g; 3mmol) be suspended in wherein; add 2-acetylaminohydroxyphenylarsonic acid 3,4,6-three-O-acetyl-2-deoxidation-α-D-Glucopyranose chloride of acid (1.2g; 3.4mmol) and phenylcarbinol (0.33g, 3mmol).Reaction solution stirred under room temperature 5 hours, TLC monitoring reaction terminal point.Reaction finishes to add a small amount of methylene dichloride dilution, the saturated sodium bicarbonate washing removes solvent under reduced pressure and gets yellow oil, adds sodium methylate-methanol solution 15ml, room temperature reaction 6h, filter acidic resins neutralization, column chromatography for separation, methyl alcohol: methylene dichloride=1: 4, obtain the white solid 0.81g of compound 58,194-196 ℃, yield 87.1%.
Embodiment 5:
A kind of preparation method of rhodioside analogue is characterized in that: concrete steps are:
(1) preparation of intermediate-acetyl glucosides
A: with radicals R 2The pure and mild required glycosyl donor R that replaces 1Acetyl-alpha-bromo-derivative be raw material, be catalyzer with silver carbonate, iodine, anhydrous calciumsulphate is a water-removal agent,
Figure BDA0000056567740000131
Molecular sieve is used to adsorb small molecules hydrogen bromide, water, under lucifuge and the exsiccant protection of inert gas, be dissolved in the corresponding non-proton organic solvent, under 15-45 ℃ (15 ℃, 25 ℃, 45 ℃ of examples), react, obtain intermediate acetyl glucose glycosides or galactoside;
Or B: with radicals R 2The pure and mild required glycosyl donor R that replaces 1Acetyl alpha-chloro thing be raw material, with zinc chloride and 4,4 '-the dimethoxytrityl methyl chloride is as catalyzer, is dissolved in corresponding non-proton organic solvent and reacts under 15-45 ℃ (15 ℃, 25 ℃, 45 ℃ of examples), obtains intermediate: the acetylize glucosaminide;
(2) rhodioside analogue preparation
The gained intermediate is taken off the acetyl protection base in containing the reagent of strong alkaline substance; Solvent is chosen as methyl alcohol, ethanol, tetrahydrofuran (THF) or ether, and the reaction times is 2-6h, and temperature of reaction is 10-40 ℃ (10 ℃, 25 ℃, 40 ℃ of examples); The gained crude product is obtained the rhodioside analogue with high-efficient liquid phase technique, column chromatography or solvent recrystallization method purifying, and (developping agent is a methyl alcohol: methylene dichloride=1: 6-1: 9) in preferred column chromatography optimization.Promptly obtain needed target compound-rhodioside and analogue thereof behind the purifying.
Non-proton organic solvent is benzene, Nitromethane 99Min., tetrahydrofuran (THF), 1 described in step (1) A, one or more mixed solvents in 2-glycol dimethyl ether, methylene dichloride, the ether.
Non-proton organic solvent is a tetrahydrofuran (THF), 1 described in step (1) B, one or several mixed solvents in 2-glycol dimethyl ether, methylene dichloride, the ether.
Strong alkaline substance described in the step (2) is sodium methylate, sodium ethylate, Anhydrous potassium carbonate, sodium hydride or sodium hydroxide.
A kind of described rhodioside analogue is used for the application of the medicine of the low serum injury protection of PC12 cell low sugar, treatment nervus centralis and peripheral nerve injury, wasting diseases in preparation.Described wasting diseases is tumour, like disease and disease of immune system now.
Attached: related compound 1The H-NMR data
1. 1H-NMR(500MHz，DMSO-d 6)：δ(ppm)9.11(1H，s，-Ph-OH)，6.65(2H，d，J＝8.5Hz)，7.02(2H，d，J＝8.5Hz)，4.90(1H，d，J＝4.5Hz)，4.86(1H，d，J＝4.5Hz)，4.83(1H，d，J＝4.9Hz)，4.43(1H，t，J＝5.8Hz)，4.15(1H，d，J＝7.8Hz).
2. 1H-NMR(500MHz，DMSO)：δ(ppm)9.12(1H，s)，7.02(2H，d，J＝8.35Hz)，6.66(2H，d，J＝6.55Hz)，4.75(1H，s)，4.62(1H，s)，4.51(1H，s)，4.28(1H，s)，4.10(1H，d，J＝7.25Hz)，3.82-3.87(1H，m)，3.62(1H，s)，3.45-3.58(3H，m)，3.27-3.32(3H，m)，2.70-2.74(2H，m).
3. 1H-NMR(D 2O，300MHz)：δ(ppm)7.38(2H，d，J＝8.2Hz)，6.95(2H，d，J＝8.2Hz)，4.80(1H，d，J＝11.3Hz)，4.63(1H，d，J＝11.3Hz)，4.38(1H，d，J＝7.32Hz)，4.01(1H)，3.73-3.76(2H，m)，3.58-3.62(2H，m)，3.40-3.49(1H，m).
4. 1H-NMR(D 2O，300MHz)：δ(ppm)7.35(2H，d，J＝8.37Hz)，6.91(2H，d，J＝8.37Hz)，4.85(1H，d，J＝11.28Hz)，4.65(1H，d，J＝11.28Hz)，4.43(1H，d，J＝7.56Hz)，3.91(1H，d，J＝3.03Hz)，3.73-3.85(2H，m)，3.59-3.69(2H，m)，3.49-3.55(1H，m).
5. 1H-NMR(500MHz，DMSO)：δ(ppm)7.38-7.40(2H，d，J＝6.95Hz)，7.30-7.34(2H，m)，7.24-7.28(1H，m)，4.90(1H，d，J＝4.85Hz)，4.81(1H，d，J＝12.30Hz)，4.63(1H，d，J＝5.45Hz)，4.53-4.57(2H，m)，4.32(1H，d，J＝4.70Hz)，4.18(1H，d，J＝7.80Hz)，3.62(1H，t，J＝3.7Hz)，3.49-3.56(2H，m)，3.25-3.27(1H，m).
6. 1H-NMR(500MHz，DMSO)：δ(ppm)7.38-7.40(2H，d，J＝6.95Hz)，7.30-7.35(2H，m)，7.25-7.28(1H，m)，4.89(1H，d，J＝4.85Hz)，4.79(1H，d，J＝12.30Hz)，4.65(1H，d，J＝5.45Hz)，4.53-4.58(2H，m)，4.33(1H，d，J＝4.70Hz)，4.18(1H，d，J＝7.70Hz)，3.64(1H，t，J＝3.65Hz)，3.49-3.57(2H，m)，325-3.27(1H，m).
7. 1H-NMR(500MHz，DMSO)：δ(ppm)7.25-7.29(4H，m)，7.17-7.20(1H，m)，3.91-3.96(1H，m)，3.62-3.68(2H，m)，3.40-3.45(1H，m)，4.91(1H，d，J＝4.95Hz)，4.86(1H，d，J＝4.86Hz)，4.83(1H，d，J＝5.10Hz)，4.43(1H，t，J＝6.0Hz)，4.17(1H，d，J＝7.80Hz)，3.11-3.15(1H，m)，3.07-3.10(1H，m)，3.01-3.05(1H，m)，2.93-2.98(1H，m)，2.83-2.87(2H，m).
8. 1H-NMR(500MHz，DMSO)：δ(ppm)7.27-7.29(2H，m)，7.25-7.26(2H，m)，7.17-7.20(1H，m)，4.76(1H，s)，4.62(1H，s)，4.50(1H，t，J＝5.45Hz)，4.29(1H，s)，4.13(1H，d，J＝7.20Hz)，3.89-3.94(1H，m)，3.62-3.66(2H，m)，3.47-3.51(2H，m)，3.29-3.34(3H)，2.83-2.87(2H，m).
9. 1H-NMR(500MHz，D 2O)：δ(ppm)7.47(4H，s)，4.93(1H，d，J＝11.55Hz)，4.53(1H，d，J＝7.20Hz)，3.93(1H，d，J＝11.55Hz)，3.76(2H，s)，3.41-3.46(4H，m).
10. 1H-NMR(500MHz，D 2O)：δ(ppm)7.37(4H，s)，4.91(1H，d，J＝11.55Hz)，4.45(1H，d，J＝6.85Hz)，3.92(1H，s)，3.77-3.80(2H，m)，3.55-3.67(4H，m).
11. 1H-NMR(D 2O，500MHz)：δ(ppm)7.58(1H)，7.38(1H，d，J＝8.28Hz)，7.55(1H，d，J＝8.37Hz)，4.97(1H，d，J＝12.39Hz)，4.86(1H，d，J＝12.39Hz)，4.52(1H，d，J＝7.89Hz)，3.89(1H)，3.74(1H)，3.42-3.47(3H，m)，3.31-3.34(1H，m).
12. 1H-NMR(D 2O，500MHz)：δ(ppm)7.55(1H)，7.45(1H，d，J＝8.58Hz)，7.38(1H，d，J＝8.28Hz)，4.97(1H，d，J＝12.4Hz)，4.85(1H，d，J＝12.4Hz)，4.46(1H，d，J＝7.47Hz)，3.92(1H，s)，3.77(2H)，3.52-3.70(3H，m).
13. 1H-NMR(D 2O，500MHz)：δ(ppm)7.42(2H，s)，7.03-7.10(2H，m)，4.91(1H，d，J＝11.7Hz)，4.78(1H，d，J＝11.75Hz)，4.50(1H，d，J＝7.85Hz)，3.91(1H，d，J＝12.55Hz)，3.86(3H，s)，3.70-3.74(1H，q，J＝4.75and?5Hz)，3.37-3.47(3H，m)，3.28(1H，t，J＝8.5Hz).
14. 1H-NMR(D 2O，500MHz)：δ(ppm)7.44(2H，t，J＝7.85Hz)，7.11(1H，d，J＝8Hz)，7.06(1H，t，J＝7.35Hz)，4.94(1H，d，J＝11.55Hz)，4.80(1H，d，J＝11.7Hz)，4.46(1H，d，J＝7.9Hz)，3.92(1H，s)，3.88(3H，s)，3.73-3.81(2H，m)，3.67(1H，d，J＝5.5Hz)，3.61(1H，d，J＝9.55Hz)，3.53(1H，t，J＝9.05?and?8.5Hz).
15. 1H-NMR(D 2O，500MHz)：δ(ppm)7.43(2H，d，J＝8.2Hz)，7.04(2H，d，J＝8.2Hz)，4.88(1H，d，J＝11.4Hz)，4.70(1H，d，J＝11.4Hz)，4.50(1H，d，J＝8.05Hz)，3.93(1H，d，J＝12.05Hz)，3.86(3H，s)，3.71-3.75(1H，dd，J＝5.7?and?5.85Hz)，3.37-3.47(3H，m)，3.29(1H，t，J＝8.2?and?8.85Hz).
16. 1H-NMR(D 2O，500MHz)：δ(ppm)7.45(2H，d，J＝7.4Hz)，7.05(2H，d，J＝7.7Hz)，4.90(1H，d，J＝11.4Hz)，4.71(1H，d，J＝11.05Hz)，4.45(1H，d，J＝7.85Hz)，3.93(1H，s)，3.86(3H，s)，3.75-3.83(2H，m)，3.68(1H，s)，3.61(1H，d，J＝9.55Hz)，3.54(1H，t，J＝8.85?and?8.9Hz).
17. 1H-NMR(D 2O，500MHz)：δ(ppm)7.16(1H，s)，7.07(2H，s)，4.89(1H，d，J＝11.5Hz)，4.72(1H，d，J＝11.5Hz)，4.51(1H，d，J＝8Hz)，3.92(1H，d，J＝10.5Hz)，3.89(6H，s)，3.71-3.76(1H，m)，3，29-3.48(3H，m)，3.31(1H，t，J＝8Hz).
18. 1H-NMR(D 2O，500MHz)：δ(ppm)7.17(1H，s)，7.07(2H，s)，4.90(1H，d，J＝11.5Hz)，4.70(1H，d，J＝9.5Hz)，4.45(1H，d，J＝8Hz)，3.92(1H，s)，3.88(6H，s)，3.75-3.83(2H，m)，3.65-3.68(1H，m)，3.61-3.63(1H，dd，J＝3.5Hz)，3.55(1H，t，J＝8Hz).
19. 1H-NMR(D 2O，500MHz)：δ(ppm)6.73(2H，s)，6.58(1H，s)，4.89(1H，d，J＝12Hz)，4.74(1H，d，J＝12.5Hz)，4.51(1H，d，J＝8Hz)，3.94(1H，d，J＝12Hz)，3.84(6H，s)，3.70-3.75(1H，m)，3.38-3.49(3H，m)，3.31(1H，t，J＝8.5Hz).
20. 1H-NMR(D 2O，500MHz)：δ(ppm)6.74(2H，s)，6.59(1H，s)，4.90(1H，d，J＝12Hz)，4.75(1H，d，J＝12.5Hz)，4.45(1H，d，J＝8Hz)，3.92(1H，s)，3.85(6H，s)，3.77-3.81(2H，m)，3.61-3.69(2H，m)，3.59(1H，t，J＝8Hz).
21. 1H?NMR(D 2O，500MHz)：δ(ppm)6.83(2H，s)，4.85(1H，d，J＝12Hz)，4.70(1H，d，J＝12Hz)，4.49(1H，d，J＝7.5Hz)，3.94(1H，d，J＝12Hz)，3.94(d，J＝12Hz，1H)，3.88(6H，s)，3.79(3H，s)，3.74-3.76(1H，m)，3.49(1H，t，J＝8.5Hz)，3.43(d，J＝7.5Hz，2H)，3.35(1H，t，J＝8.5Hz).
22. 1H?NMR(D 2O，500MHz)：δ(ppm)6.87(1H，s)，4.88(1H，d，J＝12Hz)，4.73(1H，d，J＝12Hz)，4.43(1H，d，J＝7.2Hz)，3.93(1H，d)，3.89(6H，s)，3.78-3.82(5H，m)，3.65-3.69(1H，m)，3.54-3.61(2H，m).
23. 1H?NMR(D 2O，500MHz)：δ(ppm)6.73(2H，s)，4.47(1H，d，J＝7.8Hz)，4.13-4.18(m，1H)，3.93-3.97(m，2H)，3.87(s，6H)，3.77(s，3H)，3.69-3.73(m，1H)，3.37-3.51(m，3H)，3.26(1H，t，J＝8.4Hz，)，2.93(2H，t，J＝6.5Hz).
24. 1H?NMR(D 2O，500MHz)：δ(ppm)6.73(2H，s)，4.41(1H，d，J＝7.6Hz，)，4.13-4.16(1H，m)，3.93-3.98(2H，m)，3.87(6H，s)，3.77(5H，s)，3.63-3.67(2H，m)，3.50(1H，t，J＝8.3Hz)，2.94(2H，t，J＝6.0Hz).
25. 1H?NMR(D 2O，500MHz)：δ(ppm)6.68(2H，s)，4.43(1H，d，J＝7.9Hz)，3.91-4.1(3H，m)，3.87(6H，s)，3.76(3H，s)，3.67-3.73(1H，m)，3.36-3.52(3H，m)，3.29(1H，t，J＝8.5Hz)，2.69(2H，t，J＝7.8Hz)，1.89-1.99(2H，m).
26. 1H?NMR(D 2O，500MHz)：δ(ppm)6.70(2H，s)，4.36(1H，d，J＝7.7Hz)，3.92-3.96(2H，m)，3.87(6H，s)，3.77(5H，s)，3.64-3.68(3H，m)，3.52-3.54(1H，m)，2.70(2H，t，J＝7.8Hz，)，1.91-1.99(2H，m).
27. 1H?NMR(D 2O，500MHz)：δ(ppm)6.40(2H，s)，4.38(1H，d，J＝7.9Hz)，4.0(1H，dt，J＝10.2Hz，6.8Hz)，3.75-3.85(2H，m)，3.65(1H，dd，J＝12.4Hz，5.4Hz)，3.40(1H，t，J＝8.9Hz)，3.28(2H，t，J＝4.7Hz)，3.18(1H，t，J＝8.5Hz)，2.71(2H，t，J＝6.9Hz).
28. 1H?NMR(D 2O，500MHz)：δ(ppm)6.47(2H，s)，4.38(1H，d，J＝7.7Hz)，4.02-4.12(1H，m)，3.82-3.92(2H，m)，3.76-3.78(2H，m)，3.61-3.67(2H，m)，3.49(1H，t，J＝8.8Hz)，2.79(2H，t，J＝7.0Hz).
29. 1H?NMR(D 2O，500MHz)：δ(ppm)6.43(2H，s)，4.42(1H，d，J＝7.9Hz)，3.91(2H，d，J＝11.2Hz)，3.67-3.73(2H，m)，3.38-3.52(3H，m)，3.28(1H，t，J＝8.5Hz)，2.54(2H，t，J＝7.3Hz，)，1.87(2H，t，J＝6.9Hz).
30. 1H?NMR(D 2O，500MHz)：δ(ppm)6.43(2H，s)，4.36(1H，d，J＝7.8Hz)，3.88-3.93(2H，m)，3.75-3.79(2H，m)，3.62-3.67(3H，m)，3.53(1H，t，J＝8.8Hz)，2.54(2H，t，J＝7.5Hz)，1.83-1.92(2H，m).
31. 1H?NMR(CD 3O)：δ(ppm)4.83-4.96(2H，m)，4.37(1H，d，J＝7.7Hz)，3.82-3.86(1H，m)，3.64-3.70(1H，m)，3.39-3.43(1H，m)，3.28-3.30(2H，m)，3.17(1H，t，J＝8.2Hz).
32. 1H?NMR(D 2O)：δ(ppm)4.85-4.97(2H，m)，4.45(1H，d，J＝7.6Hz)，3.95(1H，s)，3.73-3.81(2H，m)，3.54-3.71(3H，m).
33. 1H?NMR(CD 3OD)：δ(ppm)4.25(1H，d，J＝7.8Hz)，4.06(1H，dt，J＝6.9Hz，9.8Hz)，3.74-3.86(2H，m)，3.63(1H，dt，J＝2.7Hz，5.5Hz)，3.23-3.29(3H，m)，3.13(1H，t，J＝8.4Hz)，3.06(2H，t，J＝6.9Hz).
34. 1H?NMR(CD 3OD)：δ(ppm)4.20(1H，d，J＝7.6Hz)，4.01-4.09(1H，dt，J＝7.0Hz，9.6Hz)，3.73-3.81(2H，m)，3.65-3.70(2H，m)，3.43-3.50(3H，m)，3.06(2H，t，J＝7.0Hz).
35. 1H-NMR(DMSO，500MHz)：δ(ppm)7.21(2H，d，J＝7.5Hz)，7.08(2H，d，J＝7.6Hz)，5.25(1H，d，J＝8.5Hz)，4.89-4.91(1H，m)，4.80(1H，d，J＝12.5Hz)，4.76(1H，d，J＝12Hz)，4.19(1H，t，J＝9.0Hz)，4.05(1H，d，J＝12.5Hz)，3.94(2H，d，J＝12Hz)，3.61(1H，t，J＝9.0Hz)，2.88-2.80(2H，m)，2.56(2H，t，J＝8.0Hz)，2.01(3H，s)，1.96(3H，s)，1.90(3H，s)，1.85(3H，s)，2.12(3H，t，J＝7.06Hz).
36. 1H-NMR(D 2O?500MHz)：δ(ppm)7.33(1H，t，J＝7.85Hz)，7.18(1H，d，J＝7.55Hz)，6.97(1H，s)，6.90(1H，d，J＝6.25Hz)，4.89(1H，d，J＝11.8Hz)，4.71(1H，s)，4.52(1H，d，J＝7.95Hz)，3.93(1H，d，J＝10.25Hz)，3.75-3.72(1H，dd，J＝5.5Hz)，3.49-3.42(1H，m)，3.8(1H，s)，3.36-3.30(1H，m).
37. 1H-NMR(D 2O，300MHz)：δ(ppm)7.34(1H，t，J＝7.47Hz?and?J＝8.16Hz)，7.04(1H，d，J＝7.56Hz)，6.99(1H，s)，6.91(1H，d，J＝7.86Hz)，4.91(1H，d，J＝11.7Hz)，4.71(1H，d，J＝9.18Hz)，4.46(1H，d，J＝7.47Hz)，3.93(1H，s)，3.82-3.67(2H，m)，3.65-3.36(3H，m).
38. 1H-NMR(D 2O，300MHz)：δ(ppm)7.3(2H，d，J＝8.55Hz)，6.99(2H，d，J＝8.67Hz)，4.47(1H，d，J＝7.95Hz)，4.16-4.08(1H，m)，3.92-3.86(2H，m)，3.22(3H，s)，3.74-3.68(1H，dd，J＝5.45Hz)，3.50-3.34(3H，m)，3.24(1H，t，J＝8.43Hz)，2.92(2H，t，J＝6.94Hz).
39. 1H-NMR(D 2O，300MHz)：δ(ppm)7.31(2H，d，J＝7.77Hz)，6.99(2H，d，J＝7.77Hz)，4.41(1H，d，J＝7.86Hz)，4.71-4.09(1H，m)，3.91(2H，s)，3.88(3H，s)，3.83(2H，s)，3.69-3.61(2H，m)，3.49(1H，t，J＝8.3Hz)，2.92(1H，t，J＝6.70Hz).
40. 1H-NMR(D 2O，500MHz)：δ(ppm)7.24(2H，d，J＝8.1Hz)，6.96(2H，d，J＝8.15Hz)，4.41(1H，d，J＝8.0Hz)，3.90(2H，d，J＝11.1Hz)，3.82(3H，s)，3.73-3.71(1H，m)，3.66-3.62(1H，m)，3.49(1H，t，J＝8.2Hz)，3.41(1H，s)，3.29(1H，t，J＝8.6Hz)，2.66(2H，t，J＝7.45Hz)，1.91(2H，t，J＝7.1Hz).
41. 1H-NMR(D 2O，300MHz)：δ(ppm)6.98(1H，s)，6.88(1H，d，J＝7.86Hz)，6.81(1H，d，J＝8.04Hz)，4.37(1H，d，J＝7.89Hz)，3.97-3.90(2H，m)，3.87(3H，s)，3.77(2H，d，J＝8.28Hz)，3.68-3.63(3H，m)，3.53(1H，t，J＝8.75Hz)，2.67(2H，t，J＝7.4Hz)，1.93(2H，t，J＝6.96Hz).
42. 1H-NMR(D 2O，300MHz)：δ(ppm)7.19(2H，d，J＝8.37Hz)，6.86(2H，d，J＝8.37Hz)，4.42(1H，d，J＝7.95Hz)，3.91(2H，d，J＝10.89Hz)，3.75-3.61(2H，m)，3.49-3.36(3H，m)，3.28(1H，t，J＝8.52Hz)，2.65(2H，t，J＝7.48Hz)，1.90(2H，t，J＝7.47Hz?and?7.05Hz).
43. 1H-NMR(D 2O，300MHz)：δ(ppm)7.19(2H，d，J＝7.86Hz)，6.85(2H，d，J＝7.86Hz)，4.36(1H，d，J＝7.77Hz)，3.95-3.88(2H，dd，J＝9.95Hz)，3.76(2H，d，J＝8.37Hz)，3.67-3.61(3H，m)，3.51(1H，t，J＝8.58Hz?and?9.06Hz)，2.64(2H，t，J＝7.50Hz).
44. 1H-NMR(D 2O，300MHz)：δ(ppm)7.15(1H，s)，6.97(1H，d，J＝8.07Hz)，6.93(1H，d，J＝8.01Hz)，4.88(1H，s)，4.68(1H，d，J＝11.43Hz)，4.50(1H，d，J＝7.92Hz)，3.93(1H，d，J＝10.68Hz)，3.89(3H，s)，3.76-3.70(1H，m)，3.49-3.41(3H，m)，3.29(1H，t，J＝8.16Hz?and?7.68Hz).
45. 1H-NMR(D 2O，300MHz)：δ(ppm)7.17(1H，s)，6.96(2H，s)，4.88(1H，d，J＝11.31Hz)，4.69(1H，d，J＝11.7Hz)，4.45(1H，d，J＝7.26Hz)，3.93(1H，s)，3.90(3H，s)，3.81(2H，d，J＝10.89Hz)，3.68-3.55(4H，m).
46. 1H-NMR(D 2O，300MHz)：δ(ppm)6.98(1H，s)，6.88(1H，d，J＝7.86Hz)，6.81(1H，d，J＝8.07Hz)，4.37(1H，d，J＝7.89Hz)，3.97-3.90(2H，s)，3.87(3H，s)，3.24(2H，d，J＝7.56Hz)，3.65(3H，d，J＝9.66Hz)，3.53(1H，t，J＝8.70Hz)，2.67(2H，t，J＝7.47Hz)，1.93(2H，t，J＝7.00Hz).
47. 1H-NMR(D 2O，300MHz)：δ(ppm)6.98(1H，s)，6.88(1H，d，J＝7.98Hz)，6.81(1H，d，J＝8.07Hz)，4.37(1H，d，J＝7.7Hz)，4.05-3.92(2H，m)，3.53(1H，t，J＝7.86Hz)，2.67(2H，t，J＝7.55Hz)，1.93(2H，t，J＝7.22Hz).
48. 1H?NMR(D 2O，500MHz)：δ(ppm)7.00(1H，s)，6.81-6.90(2H，m)，4.46(1H，d，J＝7.9Hz)，4.12(1H，dd，J＝7.0Hz，16.7Hz)，3.89-3.93(2H，m)，3.87(3H，s)，3.71(1H，dd，J＝5.3Hz，12.2Hz)，3.34-3.50(3H，m)，3.26(1H，t，J＝8.5Hz)，2.90(2H，t，J＝6.9Hz).
49. 1H?NMR(D 2O，500MHz)：δ(ppm)7.00(1H，s)，6.82-6.89(2H，m)，4.39(1H，d，J＝7.8Hz)，4.09-4.16(1H，m)，3.89-3.92(2H，m)，3.87(3H，s)，3.74-3.79(2H，m)，3.61-3.67(2H，m)，3.50(1H，t，J＝8.8Hz)，2.90(2H，t，J＝6.7Hz).
50. 1H?NMR(D 2O，500MHz)：δ(ppm)6.70(2H，s)，4.46(1H，d，J＝7.8Hz)，4.08-4.16(1H，m)，3.89-3.93(2H，m)，3.86(6H，s)，3.72(1H，dd，J＝5.6，12.2Hz)，3.34-3.51(3H，m)，3.26(1H，t，J＝8.5Hz)，2.89(2H，t，J＝6.9Hz).
51. 1H?NMR(D 2O，500MHz)：δ(ppm)6.70(2H，s)，4.39(1H，d，J＝7.9Hz)，4.12(1H，m)，3.89-3.91(2H，m)，3.85(6H，s)，3.74-3.77(2H，m)，3.65-3.67(1H，m)，3.62(1H，dd，J＝3.4Hz，9.9Hz)，3.49(1H，dd，J＝7.9Hz，9.9Hz)，2.89(2H，t，J＝6.9Hz).
52. 1H?NMR(D 2O，500MHz)：δ(ppm)7.55(1H，s)，7.21(1H，d，J＝8.3Hz)，6.98(1H，d，J＝8.1Hz)，4.46(1H，d，J＝7.8Hz)，4.06-4.13(1H，m)，3.87-3.94(2H，m)，3.72(1H，dd，J＝5.4Hz，12.3Hz)，3.38-3.53(3H，m)，3.26(1H，t，J＝8.5Hz)，2.90(2H，t，J＝6.6Hz).
53. 1H?NMR(D 2O，500MHz)：δ(ppm)7.54(1H，s)，7.19(1H，d，J＝8.3Hz)，6.97(1H，d，J＝8.0Hz)，4.39(1H，d，J＝7.7Hz)，4.09-4.13(1H，m)，3.86-3.91(2H，m)，3.75(2H，s)，3.60-3.66(2H，m)，3.48(1H，t，J＝8.9Hz)，2.88(2H，t，J＝6.5Hz).
54. 1H?NMR(CD 3OD，500MHz)：δ(ppm)7.40(2H，s)，4.29(1H，d，J＝7.7Hz)，4.00-4.07(1H，m)，3.87(1H，d，J＝11.7Hz)，3.61-3.73(2H，m)，3.26-3.39(3H，m)，3.18(1H，t，J＝8.4Hz)，2.82(2H，t，J＝6.8Hz).
55. 1H?NMR(D 2O，500MHz)：δ(ppm)7.53(2H，s)，4.39(1H，d，J＝7.4Hz)，4.07-4.11(1H，m)，3.87-3.91(2H，m)，3.75(2H，s)，3.60-3.64(2H，m)，3.48(1H，t，J＝8.6Hz)，2.87(2H，t，J＝6.0Hz).
56. 1H?NMR(D 2O，500MHz)：δ(ppm)7.01(1H，s)，6.90(1H，d，J＝8.0Hz)，6.84(1H，d，J＝8.0Hz)，4.46(1H，d，J＝8.0Hz)，4.11-4.16(3H，m)，3.87-3.92(2H，m)，3.71(1H，dd，J＝5.7Hz，12.3Hz)，3.36-3.49(3H，m)，3.25(1H，t，J＝8.6Hz)，2.88(2H，t，J＝6.9Hz)，1.39(3H，t，J＝7.0Hz，).
57. 1H?NMR(D 2O，500MHz)：δ(ppm)7.02(H，s)，6.89(1H，d，J＝8.1Hz)，6.85(1H，d，J＝8.1Hz)，4.40(1H，d，J＝7.9Hz)，4.11-4.17(3H，m)，3.87-3.92(2H，m)，3.72-3.78(2H，m)，3.62-3.67(2H，m)，3.49(1H，t，J＝8.9Hz)，2.89(2H，t，J＝6.9Hz)，1.39(3H，t，J＝7.0Hz).
58. 1H-NMR(D 2O，300MHz)：δ(ppm)7.27(2H，d，J＝8.28Hz)，6.93(2H，d，J＝8.4Hz)，4.59(1H，d，J＝11.9Hz)，4.52(1H，d，J＝8.46Hz)，3.95(1H，d?J＝12.09Hz)，3.78-3.74(1H，m)，3.67(1H，t，J＝9.3and?8.67Hz)，3.45(4H，s)，1.91(3H，s).
59. 1H-NMR(D 2O，500MHz)：δ(ppm)7.16(2H，d，J＝7.5Hz)，6.86(2H，d，J＝8.0Hz)，4.45(1H，d，J＝8.5Hz)，4.17-4.15(1H，m)，3.92(1H，d，J＝12.5Hz)，3.74(2H，d，J＝12Hz)，3.61(1H，t，J＝9.0Hz)，3.45(2H，t，J＝11Hz)，2.86-2.78(2H，m)，1.81(1H，s)
60. 1H-NMR(D 2O，300MHz)：δ(ppm)7.16(2H，d，J＝8.4Hz)，6.87(2H，d，J＝8.3Hz)，4.5(2H，d，J＝8.5Hz)，3.94-3.85(2H，m)，3.78-3.49(4H，m)，3.44(2H，d，J＝5.57Hz)，2.59(2H，t，J＝7Hz)，2.04(3H，s)，1.83(2H，t，J＝6.66Hz).
61. 1H-NMR(D 2O?300MHz)：δ(ppm)7.33(1H，t，J＝7.77Hz)，6.94-6.87(3H，m)，4.64-4.54(1H，m)，4.53(1H，d，J＝8.4Hz)，3.84-3.66(2H，m)，3.49-3.45(4H，m)，2.0(3H，s).
62. 1H-NMR(D 2O，500MHz)：δ(ppm)7.03(1H，s)，6.94(1H，d，J＝7.95Hz)，6.89(1H，d，J＝7.95Hz)，4.53(1H，d，J＝8.4Hz)，3.90(1H，d，J＝12.25Hz)，3.89(3H，s)，3.77(1H，d，J＝9.35Hz)，3.67(1H，t，J＝9.0Hz)，3.49-3.45(3H，m)，1.89(3H，s).
63. 1H-NMR(D 2O，300MHz)：δ(ppm)6.94(1H，d，J＝7.95Hz)，6.89(1H，d，J＝8.27Hz)，6.80(1H，d，J＝8.07Hz)，4.51(1H，d，J＝8.5Hz)，3.95-3.90(2H，m)，3.87(3H，s)，3.78(2H，d，J＝7.77Hz)，3.57(2H，m)，3.46(2H，m)，2.60(2H，t，J＝7.35Hz)，2.03(3H，s)，1.85(2H，t，J＝7.2Hz).
64. 1H-NMR(D 2O，500MHz)：δ(ppm)7.24(2H，d，J＝8.5Hz)，6.98(2H，d，J＝8.5Hz)，4.46(1H，d，J＝8.5Hz)，4.17(1H，t，J＝5.0Hz)，3.93(1H，d，J＝12Hz)，3.84(3H，s)，3.82-3.73(2H，m)，3.62(1H，t，J＝9.0Hz)，3.48(1H，t，J＝9.0Hz)，3.43(1H，s)，2.88-2.80(2H，m)，1.82(3H，s).
65. 1H-NMR(CD 3OD，300MHz)：δ(ppm)7.09(2H，d，J＝8.7Hz)，6.81(2H，d，J＝7.2Hz)，4.39(1H，d，J＝8.4Hz)，3.91-3.84(2H，m)，3.75((3H，s)，3.71-3.62(2H，m)，3.49-3.41(2H，m)，3.49(1H，s)，3.28-3.25(2H，m)，2.6(2H，t，J＝6.9Hz)，1.99(3H，s)，1.8(2H，t，J＝6.9Hz)
66. 1H-NMR(D 2O，500MHz)：δ(ppm)6.62(2H，s)，6.60(1H，s)，4.84(1H，d，J＝12Hz)，4.62(1H，d，J＝10Hz)，4.54(1H，d，J＝8.5Hz)，3.95(1H，d，J＝12.5Hz)，3.85(6H，s)，3.77(1H，d，J＝10Hz)，3.70(1H，t，J＝10Hz)，3.50(1H，d，J＝10Hz)，3.47(2H，s)，1.93(3H，s).
67. 1H-NMR(D 2O，500MHz)：δ(ppm)7.23(2H，s)，6.77(1H，s)，4.82(1H，d，J＝12Hz)，4.10(1H，d，J＝10Hz)，4.02(1H，d，J＝8.5Hz)，3.92(1H，d，J＝12.5Hz)，3.86(6H，s)，3.79(2H，d，J＝10Hz)，3.70(2H，t，J＝10Hz)，3.42(1H，d，J＝10Hz)，2.72(2H，s)，1.84(3H，s).
68. 1H-NMR(D 2O，500MHz)：δ(ppm)7.46-7.37(5H，m)，4.89(1H，d，J＝12Hz)，4.89(1H，d，J＝12Hz)，4.68(1H，d，J＝12Hz)，4.54(1H，d，J＝8.4Hz)，3.95(1H，d，J＝12Hz)，3.79-3.68(2H，m)，3.46(3H，s)，1.94(3H，s).
69. 1H-NMR(D 2O，500MHz)：δ(ppm)7.38(2H，t，J＝7.55Hz)，7.29(3H，d，J＝7.35Hz)，4.47(1H，d，J＝8.5Hz)，4.19(1H，t，J＝5.5Hz)，3.92(1H，d，J＝12.05Hz)，3.88-3.82(1H，m)，3.76-3.73(1H，m)，3.62(1H，t，J＝9.2Hz)，3.48(1H，t，J＝8.5Hz)，3.42(1H，s)，2.93-2.83(2H，m)，1.83(3H，s).
70. 1H-NMR(D 2O，500MHz)：δ(ppm)8.46(1H，s)，7.24(2H，d，J＝8.07Hz)，6.90(2H，d，J＝8.07Hz)，4.70(1H，d，J＝8.9Hz)，4.12-4.17(1H，m)，3.90-3.94(2H，m)，3.72-3.76(1H，m)，3.61-3.67(1H，m)，3.45-347(2H，m)，3.01(1H，d，J＝9.27Hz)，2.89-2.95(2H，m)。
Annotate: above-mentioned numbering is corresponding with table 1.

Claims (8)

1. rhodioside analogue, it is characterized in that: chemical structural formula is:
Figure FDA0000056567730000011
R wherein 1The expression glycosyl donor is glucose, semi-lactosi, lactose, wood sugar, (N-acetyl) glucosamine, seminose or pectinose; R 2The expression phenyl ring is the substituting group on the coordination not, can be connected the optional position of phenyl ring, R 2Be specially: H, OH, Cl, Br, F, OCH 3Or OEt, but do not comprise R 1During for D (+) glucose, R 2During for hydroxyl, hydroxyl OH is connected the situation of 4 of phenyl ring; X=1-3.
2. rhodioside analogue according to claim 1; it is characterized in that: for: 2-(4-hydroxyl) styroyl-β-D-galactopyranoside; 1-(4-hydroxyl) phenmethyl-β-D-glucopyranoside; 1-(4-hydroxyl) phenmethyl-β-D-galactopyranoside; 1-phenmethyl-β-D-glucopyranoside; 1-phenmethyl-β-D-galactopyranoside; 2-styroyl-β-D-glucopyranoside; 2-styroyl-β-D-galactopyranoside; 1-(4-chlorine) phenmethyl-β-D-glucopyranoside; 1-(4-chlorine) phenmethyl-β-D-galactopyranoside; 1-(2; the 4-dichloro) phenmethyl-β-D-glucopyranoside; 1-(2; the 4-dichloro) phenmethyl-β-D-galactopyranoside; 1-(2-methoxyl group) phenmethyl-β-D-glucopyranoside; 1-(2-methoxyl group) phenmethyl-β-D-galactopyranoside; 1-(4-methoxyl group) phenmethyl-β-D-glucopyranoside; 1-(4-methoxyl group) phenmethyl-β-D-galactopyranoside; 1-(3; the 4-dimethoxy) phenmethyl-β-D-glucopyranoside; 1-(3; the 4-dimethoxy) phenmethyl-β-D-galactopyranoside; 1-(3; the 5-dimethoxy) phenmethyl-β-D-glucopyranoside; 1-(3; the 5-dimethoxy) phenmethyl-β-D-galactopyranoside; 1-(3; 4; the 5-trimethoxy) phenmethyl-β-D-glucopyranoside; 1-(3; 4; the 5-trimethoxy) phenmethyl-β-D-galactopyranoside; 2-(3; 4; the 5-trimethoxy) styroyl-β-D-glucopyranoside; 2-(3; 4; the 5-trimethoxy) styroyl-β-D-galactopyranoside; 3-(3; 4; the 5-trimethoxy) hydrocinnamyl-β-D-glucopyranoside; 3-(3; 4; the 5-trimethoxy) hydrocinnamyl-β-D-galactopyranoside; 2-(3; 4; the 5-trihydroxy-) styroyl-β-D glucopyranoside; 2-(3; 4; the 5-trihydroxy-) styroyl-β-D galactopyranoside; 3-(3; 4; the 5-trihydroxy-) hydrocinnamyl-β-D glucopyranoside; 3-(3,4, the 5-trihydroxy-) hydrocinnamyl-β-D galactopyranoside; 1-(2; 3; 4,5,6-five fluorine) phenmethyl-β-D-glucopyranoside; 1-(2; 3; 4,5,6-five fluorine) phenmethyl-β-D-galactopyranoside; 2-(2; 3; 4,5,6-five fluorine) styroyl-β-D-glucopyranoside; 2-(2; 3; 4,5,6-five fluorine) styroyl-β-D-galactopyranoside; 3-(2; 3; 4,5,6-five fluorine) hydrocinnamyl-β-D-glucopyranoside; 3-(2; 3; 4,5,6-five fluorine) hydrocinnamyl-β-D-galactopyranoside; 1-(2; 3; 5,6-tetrafluoro-4-hydroxyl) phenmethyl-β-D-glucopyranoside; 1-(2,3; 5; 6-tetrafluoro-4-hydroxyl) phenmethyl-β-D-galactopyranoside; 2-(2,3,5; 6-tetrafluoro-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(2; 3,5,6-tetrafluoro-4-hydroxyl) styroyl-β-D-galactopyranoside; 3-(2; 3; 5,6-tetrafluoro-4-hydroxyl) hydrocinnamyl-β-D-glucopyranoside; 3-(2,3; 5; 6-tetrafluoro-4-hydroxyl) hydrocinnamyl-β-D-galactopyranoside; 2-(3-methoxyl group-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3-methoxyl group-4-hydroxyl) styroyl-β-D-galactopyranoside; 2-(3,5-dimethoxy-4 '-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3,5-dimethoxy-4 '-hydroxyl) styroyl-β-D-galactopyranoside; 2-(3-bromo-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3-bromo-4-hydroxyl) styroyl-β-D-galactopyranoside; 2-(3; 5-two bromo-4-hydroxyls) styroyl-β-D-glucopyranoside; 2-(3; 5-two bromo-4-hydroxyls) styroyl-β-D-galactopyranoside; 2-(3-oxyethyl group-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3-oxyethyl group-4-hydroxyl) styroyl-β-D-galactopyranoside; 1-(3-ethanoyl-4-hydroxyl) phenmethyl-β-D-glucopyranoside; 1-(3-ethanoyl-4-hydroxyl) phenmethyl-β-D-galactopyranoside; 2-(3-ethanoyl-4-hydroxyl) styroyl-β-D-glucopyranoside; 2-(3-ethanoyl-4-hydroxyl) styroyl-β-D-galactopyranoside; 3-(3-ethanoyl-4-hydroxyl) hydrocinnamyl-β-D-glucopyranoside; 1-(4-hydroxyl) phenmethyl-2-kharophen β-D-glucopyranoside; 2-(4-hydroxyl) styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 3-(4-hydroxyl) hydrocinnamyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 1-(3-hydroxyl) phenmethyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 2-(3-hydroxyl) styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 3-(3-hydroxyl) hydrocinnamyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 2-(4-methoxyl group) styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 3-(4-methoxyl group) hydrocinnamyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 1-(3, the 5-dimethoxy) phenmethyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 2-(3, the 5-dimethoxy) styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 1-phenmethyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; 2-styroyl-2-acetylaminohydroxyphenylarsonic acid β-D-glucopyranoside; in 2-(4-hydroxyl) styroyl-2-amino-beta--D-glucopyranoside any one.
3. the preparation method of the described rhodioside analogue of claim 1, it is characterized in that: concrete steps are:
(1) preparation of intermediate-acetyl glucosides
A: with radicals R 2The pure and mild required glycosyl donor R that replaces 1Acetyl-alpha-bromo-derivative be raw material, be catalyzer with silver carbonate, iodine, anhydrous calciumsulphate is a water-removal agent,
Figure FDA0000056567730000031
Molecular sieve is used to adsorb small molecules hydrogen bromide, water, under lucifuge and the exsiccant protection of inert gas, is dissolved in the corresponding non-proton organic solvent, reacts under 15-45 ℃, obtains intermediate acetyl glucose glycosides or galactoside;
Or B: with radicals R 2The pure and mild required glycosyl donor R that replaces 1Acetyl alpha-chloro thing be raw material, with zinc chloride and 4,4 '-the dimethoxytrityl methyl chloride is as catalyzer, is dissolved in corresponding non-proton organic solvent and reacts under 15-45 ℃, obtains intermediate: the acetylize glucosaminide;
(2) rhodioside analogue preparation
The gained intermediate is taken off the acetyl protection base in containing the reagent of strong alkaline substance; Solvent is chosen as methyl alcohol, ethanol, tetrahydrofuran (THF) or ether, and the reaction times is 2-6h, and temperature of reaction is 10-40 ℃; The gained crude product is obtained the rhodioside analogue with high-efficient liquid phase technique, column chromatography or solvent recrystallization method purifying.
4. the preparation method of rhodioside analogue according to claim 3, it is characterized in that: non-proton organic solvent is benzene, Nitromethane 99Min., tetrahydrofuran (THF), 1 described in step (1) A, one or more mixed solvents in 2-glycol dimethyl ether, methylene dichloride, the ether.
5. the preparation method of rhodioside analogue according to claim 3 is characterized in that: non-proton organic solvent is a tetrahydrofuran (THF), 1 described in step (1) B, one or several mixed solvents in 2-glycol dimethyl ether, methylene dichloride, the ether.
6. the preparation method of rhodioside analogue according to claim 3 is characterized in that: the strong alkaline substance described in the step (2) is sodium methylate, sodium ethylate, Anhydrous potassium carbonate, sodium hydride or sodium hydroxide.
7. the described rhodioside analogue of claim 1 is used for the application that PC12 cell low sugar is hanged down the medicine of serum injury protection, treatment nervus centralis and peripheral nerve injury, wasting diseases in preparation.
8. rhodioside analogue according to claim 7 is used for the application of the medicine of the low serum injury protection of PC12 cell low sugar, treatment nervus centralis and peripheral nerve injury, wasting diseases in preparation, it is characterized in that: described wasting diseases is tumour, like disease and disease of immune system now.
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CN106543244B (en) * 2016-11-08 2019-07-26 山东大学 The preparation method of galactose type rhodioside and its derivative
CN109988199A (en) * 2019-04-26 2019-07-09 上海华汇拓医药科技有限公司 Rhodioside derivative and application thereof
CN109988199B (en) * 2019-04-26 2023-12-26 上海华汇拓医药科技有限公司 Rhodiola rosea glycoside derivative and application thereof

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