CN104017035A - Glucose nitrogen glycoside derivatives with 3-substituted benzylamine structure and preparation method thereof - Google Patents
Glucose nitrogen glycoside derivatives with 3-substituted benzylamine structure and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a glucose nitrogen glycoside derivatives with 3-substituted benzylamine structure, of which the general formula (I) is disclosed in the specification, wherein when R2 is hydrogen atom, R1 is hydroxy group, and R3 is hydrogen atom or hydroxy group; when R2 is methyl group, R1 is hydrogen atom, hydroxy group, methoxy group or ethoxy group, and R3 is hydrogen atom or methoxy group; and when R2 is methylene group, R1 is ether group, and R3 is hydrogen atom. The experiment proves that the glucose nitrogen glycoside derivatives with 3-substituted benzylamine structure have high antianoxic activity; and the glucose nitrogen glycoside derivatives with 3-substituted benzylamine structure have the advantage of accessible raw materials and are easy to synthesize.
Description
Technical field
The present invention relates to N-glucoside derivative of a kind of 3-of having substituted benzoyl amine structure and preparation method thereof.
Background technology
Oxygen is mankind's conditions on which persons or things depend for existence, and during anoxic, the founction metabolism of body changes, and comprises that body is to the compensatory response of anoxic and the metabolism being caused by anoxic and dysfunction.Slight hypoxia mainly causes body compensatory response; When severe depletion of oxygen and body incompensation, take metabolism obstacle as main.The formation of hypoxemia can be divided three classes: the first kind is that external environment oxygen level reduces, and makes normal physiological activity process can not absorb enough oxygen, as plateau and aviation anoxic; Equations of The Second Kind refers to because disease etc. causes extraneous normal oxygen amount and can not fully arrive in body, causes the anoxic of the heart, brain and respiratory system etc.; The 3rd class is the movable requisite oxygen consumption of body, has surpassed the physiology ability of mobilization, causes relative oxygen supply not enough, is common in strenuous exercise and the amount of transfiniting work.Long-term hypoxemia is the important hidden danger being detrimental to health, and severe patient can threat to life.Therefore, hypoxemia has become one of 21 century medical circle subject matter anxious to be resolved.
Epidemiology survey and experimental data show: high altitude anoxia can be brought out the multiple high altitude anoxia diseases such as the heart, brain, injury of the kidney, to the Plain crowd of the person of hanging up one's hat of highlands and Acute Exposed Altitude, all can bring serious health harm.Show according to the study, great majority just enter plateau persons all can there are various high altitude anoxias reactions in various degree, and as: weak, the poor appetite of having a headache, nausea and vomiting, dizzy etc., minority also there will be serious cerebral edema and pulmonary edema, and severe patient even causes death.Because acute anoxia damage causes antioxidative ability of erythrocyte significantly to decline, vasodilator activity reduces, and body vaso-active substance reduces, and resisting stress capability declines, thereby defence disease ability weakens, and the danger of suffering from the heart, cerebrovascular disease increases.
Aspect the anti-high altitude anoxia of clinical medicine, have following point at present: (1) Chinese medicine adopts Rhodiola rosea capsules, Rhodiola root oral liquid more, need take medicine in advance, and onset is slower, and each family's product effect differs.(2) compound being comprised of chemical synthetic drugs such as aminophylline, diazepam, dexamethasone and acetazolamide, can alleviate high altitude anoxia symptom, but side effect is larger.Need at present the anti-high altitude anoxia medicine of exploitation high-efficiency low-toxicity badly.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, provide the active high and raw material of a kind of anti-hypoxia to be easy to get, the N-glucoside derivative with 3-substituted benzoyl amine structure that is easy to synthesize.
Second object of the present invention is to provide a kind of preparation method of N-glucoside derivative of the 3-of having substituted benzoyl amine structure.
Technical scheme of the present invention is summarized as follows:
The N-glucoside derivative with 3-substituted benzoyl amine structure is to represent with general formula (I):
Wherein:
Work as R
2during for hydrogen atom, R
1for hydroxyl, R
3for hydrogen atom or hydroxyl;
Work as R
2during for methyl, R
1for hydrogen atom, hydroxyl, methoxy or ethoxy, R
3for hydrogen atom or methoxyl group;
Work as R
2during for methene base, R
1for ether, R
3for hydrogen atom.
The preparation method with the N-glucoside derivative of 3-substituted benzoyl amine structure, comprises the steps:
(1) in reaction vessel, add potassiumiodide or the sodium iodide of raw material (II), a katalysis, 2,3,4,6-, tetra--O-ethanoyl-1-glucosamine and DMF, under the environment of pH=10-11,60-70 ℃ of synthesis under normal pressure, TLC detects to reacting completely;
(2), by the mixed solution purification process of step (1) acquisition, obtain having the N-glucoside derivative (I) of 3-substituted benzoyl amine structure;
Described N-glucoside general formula (I) expression for derivative with 3-substituted benzoyl amine structure:
Wherein:
Work as R
2during for hydrogen atom, R
1for hydroxyl, R
3for hydrogen atom or hydroxyl;
Work as R
2during for methyl, R
1for hydrogen atom, hydroxyl, methoxy or ethoxy, R
3for hydrogen atom or methoxyl group;
Work as R
2during for methene base, R
1for ether, R
3for hydrogen atom;
Described formula (II) structural formula is:
Wherein:
Work as R
2during for hydrogen atom, R
1for hydroxyl, R
3for hydrogen atom or hydroxyl;
Work as R
2during for methyl, R
1for hydrogen atom, hydroxyl, methoxy or ethoxy, R
3for hydrogen atom or methoxyl group;
Work as R
2during for methene base, R
1for ether, R
3for hydrogen atom.
The N-glucoside derivative with 3-substituted benzoyl amine structure, R in general formula (I)
2for methyl, R
1for hydrogen atom, R
3for hydrogen atom, name is called 2-(3-p-methoxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-1).
The N-glucoside derivative with 3-substituted benzoyl amine structure, R in general formula (I)
2for methene base, R
1for ether, R
3for hydrogen atom, name is called 2-(3,4-methylenedioxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides, structural formula is (I-2):
The N-glucoside derivative with 3-substituted benzoyl amine structure, R in general formula (I)
2for methyl, R
1for methoxyl group, R
3for hydrogen atom, name is called 2-(3,4-Dimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-3).
The N-glucoside derivative with 3-substituted benzoyl amine structure, R in general formula (I)
2for methyl, R
1for oxyethyl group, R
3for hydrogen atom, name is called 2-(3-methoxyl group-4-ethoxyl phenenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-4).
The N-glucoside derivative with 3-substituted benzoyl amine structure, R in general formula (I)
2for hydrogen atom, R
1for hydroxyl, R
3for hydroxyl, name is called 2-(2,3,4-trihydroxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-5).
The N-glucoside derivative with 3-substituted benzoyl amine structure, R in general formula (I)
2for methyl, R
1for methoxyl group, R
3for methoxyl group, name is called 2-(2,3,4-trimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-6).
The N-glucoside derivative with 3-substituted benzoyl amine structure, R in general formula (I)
2for hydrogen atom, R
1for hydroxyl, R
3for hydrogen atom, name is called 2-(3,4-dihydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-7).
The N-glucoside derivative with 3-substituted benzoyl amine structure, R in general formula (I)
2during for methyl, R
1for hydroxyl, R
3for hydrogen atom, name is called 2-(3-methoxyl group-4-hydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-8).
Advantage of the present invention:
The N-glucoside derivative anti-hypoxia activity that experimental results show that the 3-of having substituted benzoyl amine structure of the present invention is high, and the N-glucoside derivative raw material of the 3-of having substituted benzoyl amine structure of the present invention is easy to get, and is easy to synthesize.
Embodiment
Below in conjunction with specific embodiment, the present invention is further illustrated.
Synthetic (I-1) of embodiment 1:2-(3-p-methoxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides
(1) in 50mL round-bottomed flask, add raw material II (1.44mmol1-brooethyl-3-anisole), play 0.14mmol potassiumiodide, the 1.44mmol2 of katalysis, 3,4,6-, tetra--O-ethanoyl-1-glucosamine and 20mLN, dinethylformamide (DMF), with sodium carbonate, adjust pH=10, atmospheric pressure reflux reaction at 60 ℃, TLC detects to reacting completely;
(2) in system, add 20mL methylene dichloride, successively with saturated sodium-chloride be washed to neutrality, anhydrous magnesium sulfate drying, remove methylene dichloride under reduced pressure, enriched material is dissolved in 20ml methyl alcohol, slowly drips the 10ml methanol solution that contains 0.1g sodium methylate under room temperature, continues to stir 2h, remove solvent under reduced pressure, carry out separated 2-(3-p-methoxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-1) that obtains of silica gel column chromatography.
1hNMR:3.07-3.40 (m, 4H, H-2, H-3, H-4, H-5), 3.58 (dd, 1H, H-6a, J
1=5.5Hz, J
2=12Hz), 3.724 (s, 3H ,-OCH
3), 4.10 (d, 1H, H-6b, J=6.8Hz), 4.63 (d, 1H, H-1, J=3.6Hz), 6.74 (d, 1H, Ph ', J=8.1Hz), 6.89 (d, 1H, Ph ', J=7.5Hz), 6.98 (s, 1H, Ph '), 7.17 (t, 1H, Ph ', J=8.1Hz); M/z=299.14 embodiment 2:2-(3,4-methylenedioxyphenyl) synthetic (I-2) of methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (structural formula is (III))
(1) in 50mL round-bottomed flask, add raw material II (1-brooethyl-3,4-methylenedioxybenzenes), play 0.14mmol sodium iodide, the 1.44mmol2 of katalysis, 3,4,6-tetra--O-ethanoyl-1-glucosamine and 20mLDMF, with sodium carbonate, adjust pH=11, atmospheric pressure reflux reaction at 70 ℃, TLC detects to reacting completely;
(2) with embodiment 1 step (2), obtain 2-(3,4-methylenedioxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-2).1HNMR:2.10(s,-NH-),3.10-3.35(m,4H,H-2,H-3,H-4,H-5),3.67(dd,1H,H-6a,J
1=6Hz,J
2=12Hz),3.85(d,1H,-CHPh′,J=12Hz),3.87(d,1H,H-6b,J=7Hz),3.95(d,1H,-CHPh′,J=8.5Hz),4.29(d,1H,H-1,J=7.5Hz),5.91(s,2H,-CH
2-),6.74(d,1H,Ph′,J=7.5Hz),6.82(d,2H,Ph′,8Hz)；MS:m/z=313.12
Synthetic (I-3) of embodiment 3:2-(3,4-Dimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides
Raw material II is 1-brooethyl-3, and 4-dimethoxy benzene adopts the method for embodiment 1 to synthesize 2-(3,4-Dimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-3), (1HNMR:2.10 s ,-NH-), 3.23-3.35 (m, 4H, H-2, H-3, H-4, H-5), 3.68 (dd, 1H, H-6a, J1=5.5Hz, J2=12Hz), 3.80 (d, 6H, 2 *-OCH
3), 3.83 (d, 1H ,-CHPh ', J=12Hz), 3.88 (d, 1H, H-6b, J=7Hz), 3.94 (d, 1H ,-CHPh ', J=8.5Hz), 4.30 (d, 1H, H-1,7.5Hz), 6.90 (d, 1H, Ph ', J=7.5Hz), 6.94 (d, 1H, Ph ', J=8Hz), 7.09 (s, 1H, Ph '); MS:m/z=329.15
Synthetic (I-4) of embodiment 4:2-(3-methoxyl group-4-ethoxyl phenenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides
Raw material II is 1-brooethyl-3-methoxyl group-4-phenetole, adopts synthetic 2-(3-methoxyl group-4-ethoxyl phenenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-4) of method of embodiment 1.1HNMR:1.31(t,-CH
3,J=6.5Hz),2.10(s,-NH-),3.21-3.34(m,4H,H-2,H-3,H-4,H-5),3.69(dd,1H,H-6a,J1=5.5Hz,J2=12Hz),3.78(s,3H,-OCH
3),3.81(m,-CH
2-,J=6.5Hz),3.84(d,1H,-CHPh′,J=12Hz),3.89(d,1H,H-6b,J=7Hz),3.95(d,1H,-CHPh′,J=8.5Hz),4.29(d,1H,H-1,7.5Hz),6.89(d,1H,Ph′,J=7.5Hz),6.93(d,1H,Ph′,J=8Hz),7.11(s,1H,Ph′)；m/z=343.16
Synthetic (I-5) of embodiment 5:2-(2,3,4-trihydroxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides
Raw material II is 1-brooethyl-2, and 3,4-trihydroxybenzene adopts the method for embodiment 1 to synthesize 2-(2,3,4-trihydroxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-5).
1HNMR:3.39-3.37(m,1H,H-3),3.45-3.41(m,1H,H-5),3.49-3.46(m,2H,H-2/H-4),3.73-3.69(dd,1H,H-6b，J
1=5.5Hz,J
2=12.0Hz,),3.89-3.86(dd,1H,H-6a，J1=2.0Hz,J2=12.0Hz,),5.10(d,J=9.0Hz,1H,H-1),m/z=317.11
Synthetic (I-6) of embodiment 6:2-(2,3,4-trimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides
Raw material II is 1-brooethyl-2, and 3,4-trimethoxy-benzene adopts the method for embodiment 1 to synthesize 2-(2,3,4-trimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-6).
1HNMR:3.40-3.38(m,1H,H-3),3.47-3.43(m,1H,H-5),3.50-3.44(m,2H,H-2/H-4),3.75-3.70(dd,1H,H-6b，J
1=5.5Hz,J
2=12.0Hz,),3.81-3.84(t,9H,3×-OCH
3),3.91-3.87(dd,1H,H-6a，J
1=2.0Hz,J
2=12.0Hz,),5.12(d,J=9.0Hz,1H,H-1)，?m/z=359.16
Synthetic (I-7) of embodiment 7:2-(3,4-dihydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides
Raw material II is 1-brooethyl-3, and 4-dihydroxy-benzene adopts the method for embodiment 1 to synthesize 2-(3,4-dihydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-7).1HNMR:2.10(s,-NH-),3.23-3.35(m,4H,H-2,H-3,H-4,H-5),3.68(dd,1H,H-6a,J1=5.5Hz,J2=12Hz),3.83(d,1H,-CHPh′,J=12Hz),3.88(d,1H,H-6b,J=7Hz),3.94(d,1H,-CHPh′,J=8.5Hz),4.30(d,1H,H-1,7.5Hz),6.98(d,1H,Ph′,J=7.5Hz),7.01(d,1H,Ph′,J=8Hz),7.12(s,1H,Ph′)；m/z=301.12
Synthetic (I-8) of embodiment 8:2-(3-methoxyl group-4-hydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides
Raw material II is 1-brooethyl-3-methoxyl group-4-hydroxybenzene, adopts synthetic 2-(3-methoxyl group-4-hydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-8) of method of embodiment 1.1HNMR:2.10(s,-NH-),3.22-3.34(m,4H,H-2,H-3,H-4,H-5),3.68(dd,1H,H-6a,J1=5.5Hz,J2=11.5Hz),3.77(s,3H,-OCH
3),3.82(d,1H,-CHPh′,J=11.5Hz),3.86(d,1H,H-6b,J=7Hz),3.91(d,1H,-CHPh′,J=8.5Hz),4.28(d,1H,H-1,7.5Hz),6.89(d,1H,Ph′,J=7.5Hz),6.97(d,1H,Ph′,J=8Hz),7.09(s,1H,Ph′)；m/z=315.13
Embodiment 9
The N-glucoside derivative with 3-substituted benzoyl amine structure prepared by each embodiment, according to a conventional method, makes various formulations as tablet, capsule, granule, soft capsule.
Embodiment 10
Pharmacologically active experimental result
The provide protection of 1 pair of Human umbilical vein endothelial cells (EA.hy926) anoxia-induced apoptosis
1.1 cells and experiment reagent: Human umbilical vein endothelial cells (EA.hy926) is U.S. GIBCO company product purchased from Chinese Academy of Sciences's Shanghai cell bank, DMEM high glucose medium.MTTWei U.S. Sigma company product; SOD and MDA test kit are purchased from building up company in Nanjing; Foetal calf serum (FBS) is purchased from hemopathy institute of the Chinese Academy of Medical Sciences.
1.2 endotheliocyte hypoxia models are set up: EA.hy926 endotheliocyte is cultivated in CO2gas incubator with the DMEM in high glucose nutrient solution (nutrient solution contains 100U/ml penicillin and 100 μ g/ml Streptomycin sulphates) that contains 10%FBS, after Growth of Cells becomes individual layer, change after the DMEM substratum cultured continuously 12h of serum-free sugar-free, use in advance with 95%N
2-5%CO
2d-hank ' the s liquid of the saturated 30min of gas mixture replaces, after normal substratum, culture plate is moved into mixed gas incubator (95%N
2, 5%CO
2, O
2concentration <1%), in 37 ℃ of anoxics, cultivate 4h, Normal group is synchronously hatched in CO2gas incubator.
1.3MTT method detects cellular metabolism vigor: the EA.hy926 endotheliocyte that is inoculated in 96 orifice plates is divided into Normal group, hypoxia model group, positive drug control group (rhodioside 1 * 10 at random
-6mol/L), (concentration is 1 * 10 to derivative group of the present invention
-6mol/L), establish 6 multiple holes, according to hypoxia model method anoxic, hatch after 4h for every group, in each sample, add MTT20 μ l, hatch a kind of rhyme scheme in Chinese operas serving as the prelude to a complete score for voices after 4h in CO2gas incubator, every hole adds dimethyl sulfoxide (DMSO) 150 μ l, fully concussion, measures absorption value in 490nm wavelength place by microplate reader.Press test kit explanation and adopt colorimetric determination SOD activity and MDA content
Detected result is as table 1.As can be seen from Table 1, with Normal group comparison, model group endotheliocyte OD value significantly reduces (P<0.01), and rhodioside can significantly improve the metabolic activity (P<0.01) of hypoxic cell; Derivative 2-(3 of the present invention, 4-methylenedioxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-2), 2-(3,4-Dimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-3), 2-(2,3,4-trihydroxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-5), 2-(3,4-dihydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-7) and 2-(3-methoxyl group-4-hydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-8)
Provide protection to anoxia-induced apoptosis endotheliocyte is better than rhodioside, and cell OD value enlarges markedly, and SOD is active to raise, and MDA content reduces (P<0.01); Derivative 2-of the present invention (3-p-methoxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-1), 2-(3 methoxyl groups-4-ethoxyl phenenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-4), 2-(2,3,4-trimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides (I-6) hypoxic endothelial cells SOD that all can raise is active, reduce MDA and produce, improve cellular metabolism vigor (P<0.01).
The impact of table 1 compound on hypoxic endothelial cells survival
Note: compare * * P<0.01, * P<0.05 with normal group; With model group comparison, ##P<0.01, #P<0.05;
Experimental result shows: the N-glucoside derivative with 3-substituted benzoyl amine structure of synthesized of the present invention can improve the SOD activity of anoxia-induced apoptosis endotheliocyte; reduce the generation of lipid peroxidation product MDA; improve cellular metabolism vigor, to cell hypoxia, damage has definite provide protection.
2 derivative I-2 of the present invention strengthen the experiment of mouse hypoxia-bearing capability
2.1 experimental techniques: 90 kunming mices are divided into totally 5 groups of solvent control groups, propranolol hydrochloride group, I-2 senior middle school low dose group, gastric infusion, gavage volume 1ml at random.The CMC-Na aqueous solution preparation that propranolol hydrochloride and I-2 are all 0.3% by mass concentration.Solvent control group gives the CMC-Na aqueous solution of equal-volume 0.3%, and propranolol hydrochloride group dosage is 20mg.Kg
-1, I-2 group dosage is respectively 20mg.Kg
-1, 10mg.Kg
-1, 5mg.Kg
-1.After administration 50min, mouse is put into 125ml wide-necked bottle (water in advance correction volume is placed 5g sodica calx in bottle), cover tightly bottle stopper, take breath stopped as sign, record the mouse survival time.
2.2 experimental results: compare with solvent control group, give 10mg.Kg
-1, 20mg.Kg
-1i-2 makes the survival time of mouse under atmospheric closed condition extend respectively 39.3% and 58.9%, and difference has significance (P<0.01) (table 2).
The impact of table 2I-2 on the hypoxia mice survival time
Note:**P<0.01vs control group;
#p<0.05vs model group,
##p<0.01vs model group.
Experimental result shows: the 2-(3 of synthesized of the present invention, 4-methylenedioxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides can significant prolongation under airtight anoxia condition survival time of mouse, there is definite oxygen lack resistant function.
Claims (10)
1. the N-glucoside derivative with 3-substituted benzoyl amine structure, is characterized in that representing with general formula (I):
Wherein:
Work as R
2during for hydrogen atom, R
1for hydroxyl, R
3for hydrogen atom or hydroxyl;
Work as R
2during for methyl, R
1for hydrogen atom, hydroxyl, methoxy or ethoxy, R
3for hydrogen atom or methoxyl group;
Work as R
2during for methene base, R
1for ether, R
3for hydrogen atom.
2. claim 1 has the preparation method of the N-glucoside derivative of 3-substituted benzoyl amine structure, and its feature comprises the steps:
(1) in reaction vessel, add potassiumiodide or the sodium iodide of raw material (II), a katalysis, 2,3,4,6-, tetra--O-ethanoyl-1-glucosamine and DMF, under the environment of pH=10-11,60-70 ℃ of synthesis under normal pressure, TLC detects to reacting completely;
(2), by the mixed solution purification process of step (1) acquisition, obtain having the N-glucoside derivative (I) of 3-substituted benzoyl amine structure;
Described N-glucoside general formula (I) expression for derivative with 3-substituted benzoyl amine structure:
Wherein:
Work as R
2during for hydrogen atom, R
1for hydroxyl, R
3for hydrogen atom or hydroxyl;
Work as R
2during for methyl, R
1for hydrogen atom, hydroxyl, methoxy or ethoxy, R
3for hydrogen atom or methoxyl group;
Work as R
2during for methene base, R
1for ether, R
3for hydrogen atom.
Described formula (II) structural formula is:
Wherein:
Work as R
2during for hydrogen atom, R
1for hydroxyl, R
3for hydrogen atom or hydroxyl;
Work as R
2during for methyl, R
1for hydrogen atom, hydroxyl, methoxy or ethoxy, R
3for hydrogen atom or methoxyl group;
Work as R
2during for methene base, R
1for ether, R
3for hydrogen atom.
3. the N-glucoside derivative with 3-substituted benzoyl amine structure according to claim 1, is characterized in that R in described general formula (I)
2for methyl, R
1for hydrogen atom, R
3for hydrogen atom, name is called 2-(3-p-methoxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides.
4. the N-glucoside derivative with 3-substituted benzoyl amine structure according to claim 1, is characterized in that R in described general formula (I)
2for methene base, R
1for ether, R
3for hydrogen atom, name is called 2-(3,4-methylenedioxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides, structural formula is (I-2):
5. the N-glucoside derivative with 3-substituted benzoyl amine structure according to claim 1, is characterized in that R in described general formula (I)
2for methyl, R
1for methoxyl group, R
3for hydrogen atom, name is called 2-(3,4-Dimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides.
6. the N-glucoside derivative with 3-substituted benzoyl amine structure according to claim 1, is characterized in that R in described general formula (I)
2for methyl, R
1for oxyethyl group, R
3for hydrogen atom, name is called 2-(3-methoxyl group-4-ethoxyl phenenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides.
7. the N-glucoside derivative with 3-substituted benzoyl amine structure according to claim 1, is characterized in that R in described general formula (I)
2for hydrogen atom, R
1for hydroxyl, R
3for hydroxyl, name is called 2-(2,3,4-trihydroxy-phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides.
8. the N-glucoside derivative with 3-substituted benzoyl amine structure according to claim 1, is characterized in that R in described general formula (I)
2for methyl, R
1for methoxyl group, R
3for methoxyl group, name is called 2-(2,3,4-trimethoxyphenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides.
9. the N-glucoside derivative with 3-substituted benzoyl amine structure according to claim 1, is characterized in that R in described general formula (I)
2for hydrogen atom, R
1for hydroxyl, R
3for hydrogen atom, name is called 2-(3,4-dihydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides.
10. the N-glucoside derivative with 3-substituted benzoyl amine structure according to claim 1, is characterized in that R in described general formula (I)
2during for methyl, R
1for hydroxyl, R
3for hydrogen atom, name is called 2-(3-methoxyl group-4-hydroxy phenyl) methyl isophthalic acid-ammonia generation-β-D-Glucose glycosides.
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