CN102093319B - 3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound, preparation method thereof and application thereof - Google Patents
3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound, preparation method thereof and application thereof Download PDFInfo
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Abstract
The invention relates to a 3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound. The 3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound has a structural general formula shown as the specifications. The 3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound has good inhibition effect on staphylococcus epidermidis, Klebsiella pneumonia, novel cryptococcus gattii and the like and can be used for preparing anti-infective medicaments for treating pneumonia, wound suppuration and the like. The invention discloses a preparation method of the 3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound.
Description
Technical field
The present invention relates to furanone type microbiotic---3-aryl-4-(2-glycosyl/amino ethoxy)-2(5
H)-furanone type compound (4-side chain amino-contained or glycosyl) and their method for making.
Technical background
The health that is endangering the mankind that pathogenic bacteria (fungi) is serious, the people more than 1/3rd is subject to the infection of this type of germ in the world, has every year more than 200 ten thousand people to die from this class and infects.Thousands of people's life has been saved in the appearance of microbiotic (antimicrobial drug) and use, the immense success that microbiotic is obtained has been benumbed people, to such an extent as to later 1960s, once the someone said that we are enough to tackle infectious diseases by existing microbiotic, did not need the new antibacterials of redeveloping.Even yet to today, we still fail thoroughly to defeat infectious diseases, it has become the second largest reason of world population death.Because bacterium (fungi) produces resistance to existing microbiotic easily, even the microbiotic that we trust most.Cause the chemical sproof topmost reason of bacterium (fungi) to be exactly: the life cycle of bacterium (fungi) is short, can be with the environment of their life of very fast velocity adaptive, very effective microbiotic before 30 years, validity has reduced greatly till now, in the future also can be lower.Therefore we to resist the strongest weapon of bacterium (fungi) be exactly to continually develop new microbiotic because bacterium (fungi) does not also produce resistance to them, thereby can bring into play potent germicidal action.
We studies show that, the enamine of acrylate type has reasonable restraining effect to bacterial growth.The analysis showed that of structure activity relationship, in two kinds of isomer of enamine,
EThe isomer of-configuration has higher activity, and
ZThe isomer of-configuration shows activity hardly.To studies show that of this compounds physico-chemical property, under nearly neutral condition
EThe isomer of-configuration can not be converted into
ZThe isomer of-configuration, but under acidic conditions
EThe isomer of-configuration can be very fast to
Z-configuration conversion is until balance is set up.This obviously can affect the performance of olefinic amine compound anti-microbial effect, and we have carried out further transformation to olefinic amine compound for this reason: introduce the furanone structural unit in molecule, and enamine functional group is replaced with enol ether functional group.This transformation can stop
E-configuration to
ZThe change of-configuration.Experiment shows that these compounds have reasonable anti-microbial activity.
Summary of the invention
The object of the invention is to take 3-virtue amino-2-aromatic substituted acrylic acid ethyl ester as primer acrylate partly be used 2(5
H)-furanone ring replaces, and recycles isosteric design philosophy, replaces enamine functional group with enol ether, has designed a series of 3-aryl-4-(2-glycosyl/amino ethoxy)-2(5
H)-furanone type compound on the basis of further investigation structure activity relationship, has been found the novel antibacterial medicine that activity is higher, toxic side effect is lower, and 3-aryl-4-(2-glycosyl/amino ethoxy is provided)-2(5
HThe method for making of)-furanone type compound.
Technical scheme of the present invention is as follows:
One class 3-aryl-4-(2-glycosyl/amino ethoxy)-2(5
H)-furanone type compound, they have following general structure:
Formula
IIn:
R
1=R
2=R
4=H
,R
3=F, Cl, Br, OH, OCH
3, NO
2Or NH
2, then: R
5=
,
,
,
,
,
,
,
,
, ,
, Azloglycoside base, altrose glycosides base, glucoside base, mannoside base, gulose glycosides base, idose glycosides base, galactoside base, talose glycosides base, riboside base, Arabinoside base, xyloside base, lyxoside base, sorb glycosyl or rhamnoside base;
R
1=R
2=R
3=H, R
4=F, Cl, Br, OH, OCH
3, NO
2Or NH
2, then: R
5=
,
,
, ,
,
, ,
, Azloglycoside base, altrose glycosides base, glucoside base, mannoside base, gulose glycosides base, idose glycosides base, galactoside base, talose glycosides base, riboside base, Arabinoside base, xyloside base, lyxoside base, sorb glycosyl or rhamnoside base;
R
1=R
2=H, then R
3=R
4=OCH
3Or OH, then: R
5=
, , , , , , ,
, Azloglycoside base, altrose glycosides base, glucoside base, mannoside base, gulose glycosides base, idose glycosides base, galactoside base, talose glycosides base, riboside base, Arabinoside base, xyloside base, lyxoside base, sorb glycosyl or rhamnoside base.
A kind of above-mentioned 3-aryl-4-(2-amino ethoxy for preparing)-2(5
HThe method of)-furanone type compound, it comprises the following steps:
Step 1. is with 2-R
1-3-R
2-4-R
3-5-R
4Substituted phenylacetic acid and sodium ethylate are dissolved in the dehydrated alcohol, at room temperature add ethyl bromoacetate, are warming up to the ratio of reaction 5-10h(amount of substance between 40-50 ℃: 2-R
1-3-R
2-4-R
3-5-R
4Substituted phenylacetic acid: sodium ethylate: ethyl bromoacetate=1:3:2), react complete, suction filtration, concentrated, the ether dilution, washing, the organic layer saturated common salt is washed to neutrality, drying, concentrated, use silica gel column chromatography, eluent is that the volume ratio of sherwood oil-AcOEt(sherwood oil and AcOEt is 20:1-5:1), obtain 2-(2-R
1-3-R
2-4-R
3-5-R
4Phenylacetyl oxygen base) ethyl acetate (
II), wherein:
R
1=R
2=R
4=H, then R
3=NO
2, F, Cl, Br, NH
2, OCH
3Or OH;
R
1=R
2=R
3=H, then R
4=F, Cl, Br, OCH
3Or OH;
R
1=R
2=H, then R
3=R
4=OCH
3Or OH;
Step 2. at room temperature joins NaH in the anhydrous tetrahydro furan (THF), then splashes into 2-(2-R
1-3-R
2-4-R
3-5-R
4Phenylacetyl oxygen base) ethyl acetate (
II) anhydrous tetrahydrofuran solution, dropwise under room temperature and react 2-7h, the ratio of amount of substance is:
II: NaH=1:1, react complete, pour in the frozen water, use extracted with diethyl ether, precipitation is separated out in the water layer acidifying, and suction filtration gets white to faint yellow solid 4-hydroxyl-3(2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2(5
H)-furanone (
III);
Step 3. is with 4-hydroxyl-3(2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2(5
H)-furanone (
III), glycol dibromide and triethylamine (ratio of amount is 1:3:2) are dissolved in anhydrous propanone, backflow 4-10h, react complete after, add water, ethyl acetate extraction, organic layer are used respectively saturated NaHCO
3Solution and saturated common salt water washing.Anhydrous MgSO
4Drying concentrates to get product 4-bromine oxethyl-3(2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2(5
H)-furanone (
IV); Will
IV,
Be dissolved among the DMF with triethylamine, the ratio of amount of substance is: IV:
: triethylamine=1:(1-4): (2-10), react 8-10h under 50 ℃ of conditions.Thin up, ethyl acetate extraction, organic layer is washed to neutrality with saturated common salt.Use anhydrous MgSO
4Drying, concentrated.Through column chromatography purification, get 3-aryl-4-(2-amino ethoxy)-2(5
H)-furanone type compound (
I), eluent is chloroform-methanol, volume ratio is (100:1)-(20:1), and adds the triethylamine of 2-5%.
R
1=R
2=R
4=H, then R
3=NO
2, F, Cl, Br, NH
2, OCH
3Or OH; R
1=R
2=R
3=H, then R
4=F, Cl, Br, OCH
3Or OH;
R
1=R
2=H, then R
3=R
4=OCH
3Or OH;
A kind of above-mentioned 3-aryl-4-(2-glycosyl oxyethyl group for preparing)-2(5
HThe method of)-furanone type compound, it is that the step 3 among the above-mentioned preparation method is substituted with following steps 3 ':
Step 3 ' the Amberlite IR-120 that will be equivalent to saccharic amount 4-7% joins in the ethylene bromohyrin, refluxes under 90 ℃ of conditions, and disposable adding carbohydrate continues to reflux, and wherein the ratio of amount of substance is: ethylene bromohyrin: carbohydrate=20:1.Then filter, filter residue washs with ethylene bromohyrin, the ethylene bromohyrin that pressure reducing and steaming is excessive, get thick crude product bromotrifluoromethane glucosides (
V), not purifiedly be directly used in next step reaction.
With the bromotrifluoromethane glucosides (
V) be dissolved in dry DMF, add again triethylamine and 4-hydroxyl-3(2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2(5
H)-furanone (
III), the ratio of amount of substance is: V: triethylamine: III=(1-3): 1:(2-10), be warming up to 50 ℃, reaction 6-10 h.React complete after, in flask, add entry.With ethyl acetate extraction 3 times, salt solution is washed till neutrality.Anhydrous MgSO
4Drying is filtered, and is concentrated, through column chromatography purification, and developping agent condition: CH
3OH:CHCl
3=1:(20-80), obtain 3-aryl-4-(2-glycosyl oxyethyl group)-2(5
H)-furanone type compound (
I).
R
1=R
2=R
4=H, then R
3=NO
2, F, Cl, Br, NH
2, OCH
3Or OH;
R
1=R
2=R
3=H, then R
4=F, Cl, Br, OCH
3Or OH;
R
1=R
2=H, then R
3=R
4=OCH
3Or OH;
R
5=Azloglycoside base, altrose glycosides base, glucoside base, mannoside base, gulose glycosides base, idose glycosides base, galactoside base, talose glycosides base, riboside base, Arabinoside base, xyloside base, lyxoside base, sorb glycosyl or rhamnoside base.
Furanone type compound of the present invention has preferably inhibition and killing action to multiple germ, and wherein some has more high bacteriostatic activity than positive control penicillin G, kantlex and KETOKONAZOL.Therefore can be for the preparation of anti-infectives.
Embodiment
Further describe the present invention by following examples, but should notice that scope of the present invention is not subjected to any restriction of these embodiment.
Embodiment 1:3-(4-bromophenyl)-and the 4-[2-(4-methylpiperazine-1-yl) oxyethyl group]-2(5
H) preparation of furanone
Step 1: with 2.7g(0.04mol) EtONa is dissolved in the 50mL dehydrated alcohol, then add 6.45g(0.030mol) to bromo-acid, wait dissolving rear adding 5.1mL(0.045mol) ethyl bromoacetate, be warming up between 40~50 ℃, reaction 10h, add water 70mL, divide three extractions with 200mLAcOEt, saturated common salt is washed to neutrality, drying, concentrated, silica gel (200-300 order) column chromatography purification (AcOEt: sherwood oil=1:6), get colorless oil (to bromobenzene acetoxy acid ethyl ester) 7.7g, productive rate 85%.
Step 2: get bromobenzene acetoxy acid ethyl ester 7.2g(0.024mol), is dissolved among the anhydrous THF of 60mL, adds 0.57gNaH(0.025mol), at room temperature stir 5h, react complete, add 100mL water, divide three extractions with the 240mL ether, water layer is separated out precipitation with the hcl acidifying of 5M, leaves standstill, filter, washing, drying gets faint yellow solid 3-(4-bromophenyl)-4-hydroxyl-2(5
H)-furanone 5.07g, productive rate 83%, fusing point: 216-218 ℃.
Step 3: with the 3-(4-bromophenyl)-4-hydroxyl-2(5
H)-furanone 3.5g(0.014mol), 12.1mL(0.14mol) glycol dibromide and 4 mL(0.028mol) triethylamine is dissolved in the 30mL acetone back flow reaction 5h.After add water 60mL, divide three extractions, the saturated NaHCO of organic layer with the 200mL ethyl acetate
3Washing, then the saturated common salt water washing is to neutrality, anhydrous MgSO
4Drying concentrates to get light yellow crystal 3-(4-bromophenyl)-4-bromine oxethyl-2(5
H)-furanone, about 3.8g, productive rate 75%, fusing point: 118-120 ℃.
Step 4: get dry good 3-(4-bromophenyl)-4-bromine oxethyl-2(5
H)-furanone 1.09g(3mmol), 0.9g(9mmol) N methyl piperazine and 1.3mL triethylamine, be dissolved in the 10mL dry DMF, be warming up to 50 ℃, the reaction 8h.Add water 30mL, divide three extractions with the 100mL ethyl acetate, saturated common salt is washed to neutrality.Anhydrous MgSO
4Drying boils off solvent.Silica gel column chromatography (elutriant: CH
3OH:CHCl
3=1:25 contains 3% triethylamine) obtain colourless transparent crystal 3-(4-bromophenyl)-the 4-[2-(4-methylpiperazine-1-yl) oxyethyl group]-2(5
H)-furanone 0.93 g, fusing point are 131-133 ℃.
Embodiment 2:3-(4-bromophenyl)-and 4-(2-glucoside base) oxyethyl group-2(5
HThe preparation of)-furanone
Step
1,Step
2 withExample
1Identical
Step
3:1.5g Amberlite IR-120 is joined in 105g (840mmol) ethylene bromohyrin, and behind backflow 30min under 90 ℃ of conditions, disposable adding glucose 7.23g (40.2mmol) continues backflow 2.5h.Filter, filter residue washs with the 10mL ethylene bromohyrin, and the ethylene bromohyrin that pressure reducing and steaming is excessive gets thick crude product, through purification by silica gel column chromatography (AcOEt:CH
3OH=18:1, v/v), get 2-bromine oxethyl glucoside 7.52g, productive rate is 65%.
Step
4:With the 3-(4-bromophenyl)-4-hydroxyl-2(5
H)-furanone 2.55g(10mmol), 2-bromine oxethyl glucoside 5.74g(20mmol), triethylamine 6.75mL is dissolved among the anhydrous 30DMF, reaction 8h.Add the dilution of 50mL water, divide three extractions with the 150mL ethyl acetate, organic layer is washed to neutrality with saturated common salt.Anhydrous MgSO
4Drying, enriched product.Through column chromatography purification (developping agent condition: CH
3OH:CHCl
3=1:30) obtain the 3-(4-bromophenyl)-4-(2-glucoside base) oxyethyl group-2(5
H)-furanone.Fusing point: 198-201 ℃.
Press embodiment 1 or 2 similar methods, be raw material with aliphatic amide and the sugar of different replacement forms, synthesized the listed 3-aryl of table 1-4-(2-glycosyl/amino ethoxy)-2(5
H)-furanone type compound
1~
88
Table 1 general formula
IMiddle 3-aryl-4-(2-glycosyl/amino ethoxy)-2(5
HEach R group of)-furanone type compound
Annotate: initial feed is all available from aldrich company
Embodiment 3: the anti-microbial activity of compound
In the MH substratum, disperse concentration to be approximately 10 bacterial suspension
5CfumL
-1Bacterium liquid is added to (every hole adds bacterium liquid 100 μ L) on 96 orifice plates, take substratum as blank, replace tested material as negative control with DMSO, gram positive bacterium is with the positive contrast of penicillin G, gram negative bacterium is with the positive contrast of kantlex, and fungi is with the positive contrast of KETOKONAZOL.Tested material is dissolved in is made into respectively 1600,800,400,200,100,50 μ gmL among the DMSO
-1Solution is (for MIC
50Less than 5 μ gmL
-1, to carry out one and go on foot when testing, the concentration gradient of preparation is 100,50,25,12.5,6.25 μ gmL
-1), join with the amount of every hole 11 μ L that [ultimate density of liquid is respectively 160,80,40,20,10,5 μ gmL on 96 orifice plates
-1(be 10,5,2.5,1.25 and 0.63 μ gmL for the latter
-1)], each concentration gradient is done four parallel laboratory tests.96 orifice plates are put into 37 ℃ incubator cultivate the 24h(fungi at 28 ℃ cultivation 48h), then add the every mL of every hole 25 μ L and contain the PBS of 4 mg MTT, under similarity condition, cultivate 4h again, add rear 12 h of cultivation of every hole 100 μ L SDS lysates (90 mL tri-distilled waters+10 g SDS+5 mL Virahol+2 mL concentrated hydrochloric acids).Under 570 nm, measure the OD value with microplate reader, calculate inhibiting rate by the formula following formula:
Inhibiting rate=[1-(tested material OD value-blank OD value)/(negative control OD value-blank OD value)] * 100
Be not less than 50% minimum concentration with inhibiting rate as the MIC of tested material
50(minimum inhibitory concentration).MIC
50Less, the activity of this compound is higher, the results are shown in Table 2.
The result shows: 3-aryl of the present invention-4-(2-glycosyl/amino ethoxy)-and 2(5
HThe anti-microbial activity of)-furanone type compound, some has higher activity than positive control penicillin G, kantlex or KETOKONAZOL.
Table 2. 3-aryl-4-(2-glycosyl/amino ethoxy)-2(5
HAnti-microbial effect (the IC of)-furanone type compound
50
)
? | MIC 50(mg/mL) | MIC 50(mg/mL) | MIC 50(mg/mL) |
Sequence number | Staphylococcus epidermidis | Klebsiella Pneumoniae | Cryptococcus neoformans |
1 | 240 | 520 | 390 |
2 | 10 | 20 | 40 |
3 | 160 | 300 | 180 |
4 | 20 | 40 | 5.8 |
5 | 75 | 102 | 85 |
6 | 5.4 | 10 | 0.52 |
7 | 90 | 105 | 140 |
8 | 15 | 20 | 40 |
9 | 15 | 10 | 20 |
10 | 0.46 | 0.33 | 0.82 |
11 | 370 | 410 | 270 |
12 | 20 | 60 | 30 |
13 | 6.2 | 3.0 | 0.55 |
14 | 108 | 160 | 240 |
15 | 80 | 60 | 40 |
16 | 10 | 5.9 | 1.0 |
17 | 20 | 10 | 80 |
18 | 325 | 500 | 670 |
19 | 10 | 25 | 30 |
20 | 0.21 | 0.62 | 0.48 |
21 | 90 | 110 | 50 |
22 | 0.22 | 0.80 | 0.16 |
23 | 40 | 10 | 30 |
24 | 80 | 105 | 75 |
25 | 3.5 | 1.5 | 0.27 |
26 | 50 | 70 | 20 |
27 | 10 | 35 | 15 |
28 | 200 | 180 | 320 |
29 | 2.5 | 1.0 | 0.81 |
30 | 55 | 60 | 40 |
31 | 40 | 15 | 21 |
32 | 60 | 42 | 36 |
33 | 1.2 | 0.84 | 0.27 |
34 | 8.4 | 15 | 10 |
35 | 45 | 70 | 120 |
36 | 10 | 4.7 | 0.89 |
37 | 90 | 107 | 110 |
38 | 5.3 | 8.2 | 4.0 |
39 | 0.14 | 0.10 | 0.25 |
40 | 78 | 45 | 30 |
41 | 360 | 430 | 320 |
42 | 65 | 150 | 225 |
43 | 0.10 | 4.4 | 8.1 |
44 | 57 | 66 | 109 |
45 | 50 | 40 | 70 |
46 | 280 | 360 | 460 |
47 | 0.64 | 0.25 | 0.36 |
48 | 0.49 | 1.3 | 1.8 |
49 | 25 | 60 | 15 |
50 | 0.88 | 13 | 16 |
51 | 15 | 10 | 1.0 |
52 | 140 | 350 | 240 |
53 | 2.5 | 0.31 | 1.0 |
54 | 106 | 178 | 210 |
55 | 15 | 20 | 10 |
56 | 0.32 | 36 | 35 |
57 | 670 | 780 | 650 |
58 | 46 | 35 | 58 |
59 | 40 | 60 | 100 |
60 | 88 | 56 | 40 |
61 | 115 | 240 | 138 |
62 | 5.3 | 10 | 35 |
63 | 85 | 100 | 60 |
64 | 5.6 | 8.0 | 10 |
65 | 2.1 | 0.36 | 5.7 |
66 | 68 | 44 | 35 |
67 | 80 | 100 | 110 |
68 | 56 | 45 | 30 |
69 | 0.18 | 0.31 | 0.56 |
70 | 22 | 65 | 16 |
71 | 280 | 443 | 368 |
72 | 0.45 | 5.8 | 6 |
73 | 95 | 105 | 80 |
74 | 80 | 38 | 50 |
75 | 4.6 | 0.25 | 30 |
76 | 60 | 40 | 65 |
77 | 0.45 | 0.18 | 0.28 |
78 | 56 | 70 | 80 |
79 | 143 | 468 | 345 |
80 | 98 | 155 | 0.61 |
81 | 50 | 60 | 45 |
82 | 59 | 64 | 30 |
83 | 360 | 545 | 470 |
84 | 10 | 5.2 | 8.7 |
85 | 10 | 25 | 30 |
86 | 116 | 128 | 205 |
87 | 75 | 49 | 30 |
88 | 0.51 | 0.70 | 0.45 |
Penicillin G | - | 0.63 | - |
Kalamycin | 1.0 | - | - |
KETOKONAZOL | - | - | 1.25 |
The result shows that compound 10,20,39,47,69,77,88 pairs of bacterium of testing all show reasonable anti-microbial activity.10,20,22,33,39,43,47,48,50,56,69,72,77,88 pairs of staphylococcus epidermidiss show good anti-microbial activity, 10,20,39,47,53,65,69,75,77,88 pairs of good anti-microbial activities of Klebsiella Pneumoniae performance, their antibacterial activity meets or exceeds penicillin G and kantlex; 6,10,12,16,20,22,25,29,33,36,39,47,51,53,69,77,80,88 pairs of Cryptococcus neoformans have good anti-microbial activity, and anti-mycotic activity meets or exceeds the positive control KETOKONAZOL.
The above embodiment of the present invention shows: 3-aryl-4-(2-glycosyl/amino ethoxy)-and 2(5
HIn the)-furanone type compound, the anti-microbial activity of some reaches or is higher than positive control penicillin G, kantlex or KETOKONAZOL.Anxious poison experiment to rat shows, compound 10,22,39,43,47,69,77 dosage reach the non-toxic that this dosage of 5g/kg(is the pharmacopeia regulation) time, do not find that rat has the poisoning sign, therefore under normal dose, they are safe as medicinal application.
The fusing point of compound 1 ~ 147, mass spectrum, infrared and hydrogen spectrum data
The 3-(4-bromophenyl)-and the 4-(2-(4-methylpiperazine-1-yl) oxyethyl group)-2(5
H)-furanone (1)
Mp?131-133℃;EIMS?m/z:380[M
+];IR(KBr)cm
-1:1682
(C=O
),3564(NH)
; 1H?NMR(CDCl
3)δppm:7.55(d,2H),7.27(d,2H),4.92(s,2H),4.37(t,2H),3.58(t,4H),3.27(s,3H),2.78(t,2H),2.41(t,4H)。
(4-bromophenyl)-4-(2-(4-oil of mirbane diazanyl) oxyethyl group)-2(5
H)-furanone (2)
Mp?180-182℃;EIMS?m/z:435[M
+];IR(KBr)cm
-1:1688(C=O),3570(NH);
1H?NMR(CDCl
3)δppm:8.18(d,2H),7.56(d,2H),7.26(d,2H),7.09(d,2H),4.95(s,2H),4.39(t,2H),4.05(s,1H),3.04(t,2H),2.06(s,1H)。
(4-bromophenyl)-4-(2-benzyl amino ethoxy)-2(5
H)-furanone (3)
Mp?145-149℃;EIMS?m/z:387[M
+];IR(KBr)cm
-1:1690(C=O),3579(NH);
?1H?NMR(CDCl
3)δppm:7.46(d,2H),7.33(d,2H),7.26(t,1H),7.23(d,2H),4.91(s,2H),4.25(t,2H),3.76(s,2H),2.92(t
,2H),2.1(s,1H)。
(4-bromophenyl)-4-[2-(piperazine-1-yl) oxyethyl group]-2(5
H)-furanone (4)
Mp?157-162℃;EIMS?m/z:380?[M
+];IR(KBr)cm
-1:1650(C=O);
1H?NMR(CDCl
3)δppm:7.46(d,2H),6.65(d,2H),5.35(s,1H),4.92(s,2H),4.23(t,2H),3.06(t,2H),2.65(t,4H),2.37(t,4H),1.91(d,1H)。
(4-bromophenyl)-4-(2-Azloglycoside base oxethyl)-2(5
H)-furanone (5)
Mp?225-254℃;EIMS?m/z:460[M
+];IR(KBr)cm
-1:?1650(C=O),3380(OH)
; 1H?NMR(DMSO-
d 6)δppm:7.58(d,2H),7.34(d,2H),4.92(s,2H),4.46(d,1H),4.13(t,2H),4.05(m,1H),3.93(m,1H),3.83(m,1H),3.76-3.80(m,2H),3.74(t,2H),3.60(m,1H)。
(4-bromophenyl)-4-(2-glucoside base oxethyl)-2(5
H)-furanone (6)
Mp?198-202℃;EIMS?m/z:460[M
+];IR(KBr)cm
-1:1720(C=O),3456(OH?);
1H?NMR(DMSO-
d 6)δppm:7.60(d,2H),7.44(d,2H),4.96(s,2H),4.56(d,1H),4.23(t,2H),4.08(m,1H),3.98(m,1H),3.86(m,1H),3.74-3.80(m,2H),3.72(t,2H),3.61(m,1H)。
(4-bromophenyl)-4-(2-gulose glycosides base oxethyl)-2(5
H)-furanone (7)
Mp?162-167℃;EIMS?m/z:460[M
+];IR(KBr)cm
-1:1710(C=O),3266(OH);
1H?NMR(DMSO-
d 6)δppm:7.59(d,2H),7.33(d,2H),4.82(s,2H),4.56(d,1H),4.12(t,2H),4.03(m,1H),3.83(m,1H),3.79(m,1H),3.75-3.78(m,2H),3.73(t,2H),3.59(m,1H)。
(4-bromophenyl)-4-(2-galactoside base oxethyl)-2(5
H)-furanone (8)
Mp?145-147℃;EIMS?m/z:460[M
+];IR(KBr)cm
-1:1710(C=O),3200(OH);
1H?NMR(DMSO-
d 6)δppm:7.68(d,2H),7.44(d,2H),4.96(s,2H),4.54(d,1H),4.18(t,2H),4.15(m,1H),3.92(m,1H),3.81(m,1H),3.76-3.79(m,2H),3.74(t,2H),3.62(m,1H),3.58(m,1H),3.46(m,1H),3.40(m,1H),3.38(m,1H)。
(4-bromophenyl)-4-(2-riboside base oxethyl)-2(5
H)-furanone (9)
Mp?188-190℃;EIMS?m/z:430[M
+];IR(KBr)cm
-1:1610(C=O),3190(OH);
1H?NMR(DMSO-
d 6)δppm:7.34(d,2H),7.31(d,2H),5.18(d,1H),4.90(s,2H),4.51(d,H),4.47(t,H),4.13(t,2H),3.76-3.80(m,2H),3.72(t,2H),3.60(m,H),3.56(t,H),3.48(m,1H),3.29(m,1H)。
(4-bromophenyl)-4-(2-xyloside base oxethyl)-2(5
H)-furanone (10)
Mp?155-157℃;EIMS?m/z:430[M
+];IR(KBr)cm
-1:1690(C=O),3321(OH);
1H?NMR(DMSO-
d 6)δppm:7.32(d,2H),7.30(d,2H),5.16(d,1H),4.92(s,2H),4.57(d,1H),4.37(t,1H),4.23(t,2H),3.74-3.76(m,2H),3.72(t,2H),3.59(m,1H),3.56(t,1H),3.46(m,1H),3.32(m,1H)。
(4-bromophenyl)-4-(2-sorb glucosides base oxethyl)-2(5
H)-furanone (11)
Mp?160-164℃;EIMS?m/z:448[M
+];IR(KBr)cm
-1:1680(C=O),3350(OH?);
1H?NMR(DMSO-
d 6)δppm:7.68(d,2H),7.54(d,2H),4.88(s,2H),4.48(d,1H),4.25(t,2H),4.10(m,1H),3.98(m,1H),3.82(m,1H),3.75-3.81(m,2H),3.72(t,2H),3.66(m,1H),3.59(m,1H),3.53(m,1H),3.42(m,1H),3.33(m,1H)。
(4-hydroxy phenyl)-4-(2-(4-methylpiperazine-1-yl) oxyethyl group)-2(5
H)-furanone (12)
Mp?166-168℃;EIMS?m/z:318[M
+];IR(KBr)cm
-1:1680(C=O);
1H?NMR(DMSO-
d 6)δppm:7.54(d,2H),7.28(d,4H),5.38(s,1H),4.90(s,2H),4.38(t,2H),3.59(t,4H),3.29(s,3H),2.76(t,2H),2.45(t,4H)。
(4-hydroxy phenyl)-4-[2-(4-nitrophenyl hydrazine) oxyethyl group]-2(5
H)-furanone (13)
Mp?169-171℃;EIMS?m/z:371[M
+];IR(KBr)cm
-1:1688(C=O),3650(NH);
1H?NMR(DMSO-
d 6)δppm:8.16(d,2H),7.58(d
,2H),7.36(d,2H),7.05(d,2H),5.85(s,1H),4.91(s,2H),4.49(t,2H),4.04(s,1H),3.19(t,2H),2.06(s,1H)。
(4-hydroxy phenyl)-4-(2-benzamido group oxyethyl group)-2(5
H)-furanone (14)
Mp?149-151℃;EIMS?m/z:325[M
+];IR(KBr)cm
-1:1690(C=O),3478(NH);
1H?NMR(DMSO-
d 6)δppm:7.48(d,2H),7.35(d,2H),7.29(t,1H),7.18(d,2H),5.45(s,1H),4.98(s,2H),4.26(t,2H),3.86(s,2H),2.92(t,2H),2.16(s,1H)。
(4-hydroxy phenyl)-4-[2-(piperazine-1-yl) oxyethyl group]-2(5
H)-furanone (15)
Mp?167-169℃;EIMS?m/z:304[M
+];IR(KBr)cm
-1:1650(C=O),3657(NH)
; 1H?NMR(DMSO-
d 6)δppm:7.56(d,2H),5.65(d,2H),5.36(s,1H),5.33(s,1H),4.82(s,2H),4.28(t,2H),3.36(t,2H),2.69(t,4H),2.36(t,4H),1.89(d,1H)。
(4-hydroxy phenyl)-4-(2-Azloglycoside base oxethyl)-2(5
H)-furanone (16)
Mp?164-156℃;EIMS?m/z:398[M
+];IR(KBr)cm
-1:1650(C=O),3300(OH);
1H?NMR(DMSO-
d 6)δppm:7.13(d,2H),7.05(d,2H),5.35(s,H),4.72(s,2H),4.56(d,1H),4.33(t,2H),4.15(m,1H),3.90(m,1H),3.85(m,1H),3.76-3.82(m,2H),3.73(t,2H),3.50(m,1H)。
(4-hydroxy phenyl)-4-(2-glucoside base oxethyl)-2(5
H)-furanone (17)
Mp?159-161℃;EIMS?m/z:398[M
+];IR(KBr)cm
-1:1650(C=O),3245(OH);
1H?NMR(DMSO-
d 6)δppm:7.23(d,2H),7.06(d,2H),5.45(s,1H),4.78(s,2H),4.50(d,1H),4.32(t,2H),4.18(m,1H),3.94(m,1H),3.95(m,1H),3.79-3.85(m,2H),3.72(t,2H),3.58(m,1H)。
(4-hydroxy phenyl)-4-(2-(gulose glycosides base oxethyl)-2(5
H)-furanone (18)
Mp?147-149℃;EIMS?m/z:398[M
+];IR(KBr)cm
-1:1650(C=O),3356(OH);
1H?NMR(DMSO-
d 6)δppm:7.32(d,2H),7.18(d,2H),5.42(s,1H),4.70(s,2H),4.66(d,1H),4.43(t,2H),4.16(m,1H),3.98(m,1H),3.87(m,1H),3.79-3.83(m,2H),3.74(t,2H),3.40(m,1H)。
(4-hydroxy phenyl)-4-(2-galactoside base oxethyl)-2(5
H)-furanone (19)
Mp?165-167℃;EIMS?m/z:398[M
+];IR(KBr)cm
-1:1650(C=O),3342(OH);
1H?NMR(DMSO-
d 6)δppm:7.09(d,2H),6.99(d,2H),5.25(s,1H),4.78(s,2H),4.54(d,1H),4.32(t,2H),4.18(m,1H),3.96(m,1H),3.82(m,1H),3.76-3.80(m,2H),3.73(t,2H),3.62(m,1H)。
(4-hydroxy phenyl)-4-(2-riboside base oxethyl)-2(5
H)-furanone (20)
Mp?161-163℃;EIMS?m/z:368[M
+];IR(KBr)cm
-1:1650(C=O),3285(OH);
1H?NMR(DMSO-
d 6)δppm:7.28(d,2H),7.24(d,2H),5.35(d,1H),5.21(d,1H),4.99(s,2H),4.56(d,1H),4.44(t,1H),4.15(t,2H),3.76-3.88(m,2H),3.70(t,2H),3.66(m,H),3.54(t,H),3.46(m,1H),3.39(m,1H)。
(4-hydroxy phenyl)-4-(2-xyloside base oxethyl)-2(5
H)-furanone (21)
Mp?171-173℃;EIMS?m/z:368[M
+];IR(KBr)cm
-1:1650(C=O),3360(OH);
1H?NMR(DMSO-
d 6)δppm:7.28(d,2H),7.14(d,2H),5.45(d,1H),5.26(d,1H),4.92(s,2H),4.52(d,1H),4.48(t,1H),4.23(t,2H),3.75-3.80(m,2H),3.74(t,2H),3.55(m,H),3.42(t,H),3.38(m,1H),3.26(m,1H)。
(4-hydroxy phenyl)-4-(2-sorb glucosides base oxethyl)-2(5
H)-furanone (22)
Mp?163-165℃;EIMS?m/z:406[M
+];IR(KBr)cm
-1:1650(C=O),3345(OH);
1H?NMR(DMSO-
d 6)δppm:7.32(d,2H),7.19(d,2H),5.36(d,1H),5.20(d,1H),5.15(s,1H),4.76(s,2H),4.52(d,1H),4.42(t,2H),4.17(m,1H),3.92(m,1H),3.84(m,1H),3.78-3.80(m,2H),3.72(t,2H),3.52(m,1H)。
(4-fluorophenyl)-4-(2-(4-methylpiperazine-1-yl) oxyethyl group)-2(5
H)-furanone (23)
Mp?156-158℃;EIMS?m/z:320[M
+];IR(KBr)cm
-1:1688(C=O);
1H?NMR(CDCl
3)δppm:7.52(d,2H),7.37(d,2H),4.88(s,2H),4.36(t,2H),3.48(t,4H),3.29(s,3H),2.58?(t,2H),2.46(t,4H)。
(4-fluorophenyl)-4-[2-(4-oil of mirbane diazanyl) oxyethyl group]-2(5
H)-furanone (24)
Mp?157-159℃;EIMS?m/z:435[M
+];IR(KBr)cm
-1:1688(C=O),3588(NH);
1H?NMR(CDCl
3)δppm:8.10(d,2H),7.54(d,2H),7.23(d,2H),7.05(d,2H),4.85(s,2H),4.30(t,2H),4.15(s,1H),3.14(t,2H),2.24(s,1H)。
(4-fluorophenyl)-4-(2-benzamido group oxyethyl group)-2(5
H)-furanone (25)
Mp?177-179℃;EIMS?m/z:327[M
+];IR(KBr)cm
-1:1695(C=O),3600(NH
); 1H?NMR(CDCl
3)δppm:7.65(d,2H),7.23(d,2H),7.28(t,1H),7.22(d,2H),4.81(s,2H),4.23(t,2H),3.78(s,2H),2.90(t
,2H),2.18(s,1H)。
(4-fluorophenyl)-4-[2-(piperazine-1-yl) oxyethyl group]-2(5
H)-furanone (26)
Mp?160-162℃;EIMS?m/z:306[M
+];IR(KBr)cm
-1:1650(C=O),3542(NH);
1H?NMR(CDCl
3)δppm:7.52(d,2H),6.95(d,2H),5.65(s,1H),4.96(s,2H),4.24(t,2H),3.08(t,2H),2.67(t
,4H),2.47(t,4H),1.98(d,1H)。
(4-fluorophenyl)-4-(2-Azloglycoside base oxethyl)-2(5
H)-furanone (27)
Mp?156-158℃;EIMS?m/z:400[M
+];IR(KBr)cm
-1:1688(C=O),3566(OH);
1H?NMR(DMSO-
d 6)δppm:7.68(d,2H),7.54(d,2H),4.86(s,2H),4.57(d,1H),4.33(t,2H),4.18(m,1H),3.99(m,1H),3.84(m,1H),3.70-3.82(m,2H),3.68(t,2H),3.60(m,1H)。
(4-fluorophenyl)-4-(2-glucoside base oxethyl)-2(5
H)-furanone (28)
Mp?182-183℃;EIMS?m/z:400[M
+];IR(KBr)cm
-1:1650(C=O),3228(OH);
1H?NMR(DMSO-
d 6)δppm:7.66(d,2H),7.42(d,2H),4.94(s,2H),4.54(d,1H),4.20(t,2H),4.28(m,1H),3.96(m,1H),3.75(m,1H),3.62-3.81(m,2H),3.71(t,2H),3.59(m,1H)。
(4-fluorophenyl)-4-(2-(gulose glycosides base oxethyl)-2(5
H)-furanone (29)
Mp?170-172℃;EIMS?m/z:400[M
+];IR(KBr)cm
-1:1665(C=O),3321(OH)
; 1H?NMR(DMSO-
d 6)δppm:7.34(d,2H),7.25(d,2H),4.93(s,2H),4.66(d,1H),4.27(t,2H),4.06(m,1H),3.95(m,1H),3.84(m,1H),3.71-3.80(m,2H),3.62(t,2H),3.55(m,1H)。
(4-fluorophenyl)-4-(2-galactoside base oxethyl)-2(5
H)-furanone (30)
Mp?165-167℃;EIMS?m/z:400[M
+];IR(KBr)cm
-1:1660(C=O),3400(OH);
1H?NMR(DMSO-
d 6)δppm:7.49(d,2H),7.44(d,2H),4.95(s,2H),4.51(d,1H),4.20(t,2H),4.09(m,1H),3.91(m,1H),3.80(m,1H),3.74-3.79(m,2H),3.71(t,2H),3.51(m,1H)。
(4-fluorophenyl)-4-(2-riboside base oxethyl)-2(5
H)-furanone (31)
Mp?151-153℃;EIMS?m/z:370[M
+];IR(KBr)cm
-1:1678(C=O),3300(OH);
1H?NMR(DMSO-
d 6)δppm:7.45(d,2H),7.38(d,2H),5.28(d,1H),4.91(s,2H),4.59(d,1H),4.46(t,1H),4.11(t,2H),3.73-3.86(m,2H),3.70(t,2H),3.64(m,1H),3.53(t,1H),3.42(m,1H),3.26(m,1H)。
(4-fluorophenyl)-4-(2-xyloside base oxethyl)-2(5
H)-furanone (32)
Mp?161-163℃;EIMS?m/z:370[M
+];IR(KBr)cm
-1:1550(C=O),3545(OH);
1H?NMR(DMSO-
d 6)δppm:7.42(d,2H),7.26(d,2H),5.16(d,H),4.92(s,2H),4.55(d,1H),4.46(t,1H),4.12(t,2H),3.76(m,2H),3.72(t,2H),3.66(m,1H),3.54(t,1H),3.42(m,1H),3.39(m,1H)。
(4-fluorophenyl)-4-(2-sorb glucosides base oxethyl)-2(5
H)-furanone (33)
Mp?171-173℃;EIMS?m/z:326[M
+];IR(KBr)cm
-1:1658(C=O),3665(OH);
1H?NMR(DMSO-
d 6)δppm:7.65(d,2H),7.42(d,2H),4.86(s,2H),4.54(d,1H),4.28(t,2H),4.13(m,1H),3.93(m,1H),3.82(m,1H),3.80(m,2H),3.76(t,2H),3.65(m,1H)。
(4-nitrophenyl)-4-(2-(4-methylpiperazine-1-yl) oxyethyl group)-2(5
H)-furanone (34)
Mp?166-168℃;EIMS?m/z:347[M
+];IR(KBr)cm
-1:1680(C=O),3524(NH)
; 1H?NMR(CDCl
3)δppm:7.51(d,2H),7.36(d,4H),4.94(s,2H),4.36(t,2H),3.56(t,4H),3.37(s,3H),2.75(t,2H),2.46(t,4H)。
(4-nitrophenyl)-4-(2-(4-oil of mirbane diazanyl) oxyethyl group)-2(5
H)-furanone (35)
Mp?169-171℃;EIMS?m/z:400[M
+];IR(KBr)cm
-1:1688(C=O),3648(NH);
1H?NMR(CDCl
3)δppm:8.16(d,2H),7.63(d,2H),7.31(d,2H),7.13(d,2H),4.92(s,2H),4.41(t,2H),4.15(s,1H),3.08(t,2H),2.26(s,1H)。
(4-nitrophenyl)-4-(2-benzyl amino ethoxy)-2(5
H)-furanone (36)
Mp?162-164℃;EIMS?m/z:354[M
+];IR(KBr)cm
-1:1694(C=O),3550(NH);
1H?NMR(CDCl
3)δppm:7.45(d,2H),7.23(d,2H),7.28(t,1H),7.13(d,2H),4.92(s,2H),4.28(t,2H),3.78(s,2H),2.90(t,2H),2.19(s,1H)。
(4-nitrophenyl)-4-[2-(piperazine-1-yl) oxyethyl group]-2(5
H)-furanone (37)
Mp?172-174℃;EIMS?m/z:333[M
+];IR(KBr)cm
-1:1684(C=O),3567(NH);
1H?NMR(CDCl
3)δppm:7.52(d,2H),6.95(d,2H),5.38(s,1H),4.89(s,2H),4.43(t,2H),3.09(t,2H),2.69(t,4H),2.39(t,4H),1.95(d,1H)。
(4-nitrophenyl)-4-(2-Azloglycoside base oxethyl)-2(5
H)-furanone (38)
Mp?151-153℃;EIMS?m/z:427[M
+];IR(KBr)cm
-1:1450(C=O),3348(OH);
1H?NMR(DMSO-
d 6)δppm:7.60(d,2H),7.44(d,2H),4.96(s,2H),4.56(d,1H),4.23(t,2H),4.08(m,1H),3.98(m,1H),3.86(m,1H),3.74-3.80(m,2H),3.72(t,2H),3.61(m,1H)。
(4-nitrophenyl)-4-(2-glucoside base oxethyl)-2(5
H)-furanone (39)
Mp?159-161℃;EIMS?m/z:427[M
+];IR(KBr)cm
-1:1650(C=O),3299(OH);
1H?NMR(DMSO-
d 6)δppm:7.60(d,2H),7.44(d,2H),4.96(s,2H),4.56(d,1H),4.23(t,2H),4.08(m,1H),3.98(m,1H),3.86(m,1H),3.74-3.80(m,2H),3.72(t,2H),3.61(m,1H)。
(4-nitrophenyl)-4-(2-(gulose glycosides base oxethyl)-2(5
H)-furanone (40)
Mp?147-149℃;EIMS?m/z:427[M
+];IR(KBr)cm
-1:1568(C=O),3457(OH);
1H?NMR(DMSO-
d 6)δppm:7.60(d,2H),7.44(d,2H),4.96(s,2H),4.56(d,1H),4.23(t,2H),4.08(m,1H),3.98(m,1H),3.86(m,1H),3.74-3.80(m,2H),3.72(t,2H),3.61(m,1H)。
(4-nitrophenyl)-4-(2-galactoside base oxethyl)-2(5
H)-furanone (41)
Mp?145-147℃;EIMS?m/z:427[M
+];IR(KBr)cm
-1:1659(C=O),3367(OH);
1H?NMR(DMSO-
d 6)δppm:7.60(d,2H),7.44(d,2H),4.96(s,2H),4.56(d,1H),4.23(t,2H),4.08(m,1H),3.98(m,1H),3.86(m,1H),3.74-3.80(m,2H),3.72(t,2H),3.61(m,1H)。
(4-nitrophenyl)-4-(2-riboside base oxethyl)-2(5
H)-furanone (42)
Mp?154-156℃;EIMS?m/z:397[M
+];IR(KBr)cm
-1:1679(C=O),3423(OH);
1H?NMR(DMSO-
d 6)δppm:7.45(d,2H),7.36(d,2H),5.18(d,H),4.98(s,2H),4.67(d,1H),4.36(t,1H),4.21(t,2H),3.74-3.78(m,2H),3.70(t,2H),3.54(m,1H),3.52(t,1H),3.36(m,1H),3.32(m,1H)。
(4-nitrophenyl)-4-(2-xyloside base oxethyl)-2(5
H)-furanone (43)
Mp?144-146℃;EIMS?m/z:397[M
+];IR(KBr)cm
-1:1698(C=O),3545(OH);
1H?NMR(DMSO-
d 6)δppm:7.38(d,2H),7.27(d,2H),5.12(d,1H),4.88(s,2H),4.56(d,1H),4.41(t,1H),4.18(t,2H),3.74(m,2H),3.68(t,2H),3.52(m,1H),3.45(t,1H),3.39(m,1H),3.22(m,1H)。
(4-nitrophenyl)-4-(2-sorb glucosides base oxethyl)-2(5
H)-furanone (44)
Mp?149-151℃;EIMS?m/z:381[M
+];IR(KBr)cm
-1:1550(C=O),3542(OH);
1H?NMR(DMSO-
d 6)δppm:7.68(d,2H),7.54(d,2H),4.98(s,2H),4.64(d,1H),4.32(t,2H),4.08(m,1H),3.98(m,1H),3.84(m,1H),3.75(m,2H),3.72(t,2H),3.68(m,1H)。
(4-aminophenyl)-4-(2-(4-methylpiperazine-1-yl) oxyethyl group)-2(5
H)-furanone (45)
Mp?150-153℃;EIMS?m/z:317[M
+];IR(KBr)cm
-1:1456(C=O),3448(NH);
1H?NMR(CDCl
3)δppm:7.23(d,2H),7.18(d,4H),6.27(s,2H),4.92(s,2H),4.37(t,2H),3.58(t,4H),3.27(s,3H),2.78(t,2H),2.41(t,4H)。
(4-aminophenyl)-4-(2-(4-oil of mirbane diazanyl) oxyethyl group)-2(5
H)-furanone (46)
Mp?161-163℃;EIMS?m/z:370[M
+];IR(KBr)cm
-1:1688(C=O),3392(NH);
1H?NMR(CDCl
3)δppm:7.28(d,2H),7.15(d,2H),7.03(d,2H),6.39(d,2H),6.26(m,2H),4.94(s,2H),4.69(t,2H),4.35(s,1H),3.24(t,2H),2.28(s,1H)。
(4-aminophenyl)-4-(2-benzyl amino ethoxy)-2(5
H)-furanone (47)
Mp?168-170℃;EIMS?m/z:324[M
+];IR(KBr)cm
-1:1590(C=O),3564(NH);
1H?NMR(CDCl
3)δppm:7.35(d,2H),7.13(d,2H),7.08(t,H),7.03(d,2H),6.24(m,2H),4.91(s,2H),4.22(t,2H),3.79(s,2H),2.94(t,2H),2.18(s,1H)。
(4-aminophenyl)-4-[2-(piperazine-1-yl) oxyethyl group]-2(5
H)-furanone (48)
Mp?158-160℃;EIMS?m/z:303[M
+];IR(KBr)cm
-1:1680(C=O),3368(NH);
1H?NMR(CDCl
3)δppm:7.29(d,2H),7.23(d,2H),7.16(t,1H),7.03(d,2H),6.22(s,2H),4.96(s,2H),4.23(t,2H),3.73(s,2H),2.82(t,2H),1.96(s,1H)。
(4-aminophenyl)-4-(2-Azloglycoside base oxethyl)-2(5
H)-furanone (49)
Mp?169-171℃;EIMS?m/z:397[M
+];IR(KBr)cm
-1:1670(C=O),3267(OH);
1H?NMR(DMSO-
d 6)δppm:7.28(d,2H),7.20(d,2H),6.35(m,2H),4.91(s,2H),4.58(d,1H),4.26(t,2H),4.18(m,1H),3.96(m,1H),3.84(m,1H),3.80(m,2H),3.62(t,2H),3.55(m,1H)。
(4-aminophenyl)-4-(2-glucoside base oxethyl)-2(5
H)-furanone (50)
Mp?173-175℃;EIMS?m/z:397[M
+];IR(KBr)cm
-1:1480(C=O),3198(OH);
1H?NMR(DMSO-
d 6)δppm:7.29(d,2H),7.13(d,2H),6.40(m,2H),4.92(s,2H),4.46(d,1H),4.13(t,2H),4.02(m,1H),3.96(m,1H),3.76(m,1H),3.74(m,2H),3.60(t,2H),3.23(m,1H)。
(4-aminophenyl)-4-(2-(gulose glycosides base oxethyl)-2(5
H)-furanone (51)
Mp?165-167℃;EIMS?m/z:397[M
+];IR(KBr)cm
-1:1694(C=O),3349(OH);
1H?NMR(DMSO-
d 6)δppm:7.26(d,2H),7.15(d,2H),6.39(m,2H),4.93(s,2H),4.45(d,1H),4.03(t,2H),3.96(m,1H),3.75(m,1H),3.66(m,1H),3.42(m,2H),3.38(t,2H),3.15(m,1H)。
(4-aminophenyl)-4-(2-galactoside base oxethyl)-2(5
H)-furanone (52)
Mp?155-157℃;EIMS?m/z:397[M
+];IR(KBr)cm
-1:1587(C=O),3300(OH);
1H?NMR(DMSO-
d 6)δppm:7.48(d,2H),7.24(d,2H),6.38(m,2H),4.91(s,2H),4.53(d,1H),4.20(t,2H),4.02(m,1H),3.96(m,1H),3.82(m,1H),3.76-3.80(m,2H),3.72(t,2H),3.43(m,1H)。
(4-aminophenyl)-4-(2-riboside base oxethyl)-2(5
H)-furanone (53)
Mp?157-159℃;EIMS?m/z:367[M
+];IR(KBr)cm
-1:1660(C=O),3321(OH);
1H?NMR(DMSO-
d 6)δppm:7.25(d,2H),7.06(d,2H),6.34(m,2H),5.21(d,H),4.94(s,2H),4.65(d,1H),4.32(t,1H),4.20(t,2H),3.78(m,2H),3.72(t,2H),3.51(m,H),3.46(t,H),3.26(m,1H),3.02(m,1H)。
(4-aminophenyl)-4-(2-xyloside base oxethyl)-2(5
H)-furanone (54)
Mp?154-156℃;EIMS?m/z:367[M
+];IR(KBr)cm
-1:1648(C=O),3545(OH);
1H?NMR(DMSO-
d 6)δppm:7.40(d,2H),7.26(d,2H),6.35(m,2H),5.17(d,1H),4.92(s,2H),4.68(d,1H),4.34(t,1H),4.11(t,2H),3.74-3.81(m,2H),3.70(t,2H),3.49(m,1H),3.40(t,1H),3.36(m,1H),3.28(m,1H)。
(4-aminophenyl)-4-(2-sorb glucosides base oxethyl)-2(5
H)-furanone (55)
Mp?160-162℃;EIMS?m/z:319[M
+];IR(KBr)cm
-1:1655(C=O),3660(OH);
1H?NMR(DMSO-
d 6)δppm:7.25(d,2H),7.16(d,2H),6.45(m,2H),4.90(s,2H),4.36(d,1H),4.23(t,2H),4.03(m,1H),3.95(m,1H),3.86(m,1H),3.74-3.81(m,2H),3.68(t,2H),3.55(m,1H)。
(3-p-methoxy-phenyl)-4-(2-(4-methylpiperazine-1-yl) oxyethyl group)-2(5
H)-furanone (56)
Mp?154-156℃;EIMS?m/z:332[M
+];IR(KBr)cm
-1:?1680(C=O)?,3340(NH);
1H?NMR(CDCl
3)δppm:7.59(d,H),6.93(d,H),6.87(m,2H),4.92(s,H),4.23(t,2H),3.83(s,3H),3.03(t,1H),2.35(s,4H),2.36(s,4H)。
(3-p-methoxy-phenyl)-4-(2-(4-oil of mirbane diazanyl) oxyethyl group)-2(5
H)-furanone (57)
Mp?163-165℃;EIMS?m/z:385[M
+];IR(KBr)cm
-1:1688(C=O),3352(NH);
1H?NMR(CDCl
3)δppm:7.62(d,H),6.94(d,H),6.85(m,2H),6.42(d,2H),4.91(s,2H),4.60(t,2H),4.32(s,1H),3.81(s,3H),3.22(t,2H),2.20(s,1H)。
(3-p-methoxy-phenyl)-4-(2-benzyl amino ethoxy)-2(5
H)-furanone (58)
Mp?173-175℃;EIMS?m/z:339[M
+];IR(KBr)cm
-1:1690(C=O),3628(NH);
1H?NMR(CDCl
3)δppm:7.32(d,2H),7.12(d,1H),7.08(d,2H),6.91(d,1H),6.80(m,2H),4.91(s,2H),4.12(t,2H),3.81(s,3H),3.69(s,2H),2.92(t,2H),2.12(s,H)。
(3-p-methoxy-phenyl)-4-[2-(piperazine-1-yl) oxyethyl group]-2(5
H)-furanone (59)
Mp?159-161℃;EIMS?m/z:318[M
+];IR(KBr)cm
-1:1645(C=O),3548(NH);
1H?NMR(CDCl
3)δppm:7.30(d,2H),6.92(d,H),6.81(m,2H),4.92(s,2H),4.21(t,2H),3.85(s,3H),3.72(s,2H),2.72(t,2H),1.98(s,1H)。
(3-p-methoxy-phenyl)-4-(2-altrose glycosides base oxethyl)-2(5
H)-furanone (60)
Mp?149-151℃;EIMS?m/z:412[M
+];IR(KBr)cm
-1:1550(C=O),3368(OH);
1H?NMR(DMSO-
d 6)δppm:7.56(d,2H),6.98(d,1H),6.82(m,2H),4.96(s,2H),4.56(d,1H),4.18(t,2H),4.02(m,1H),3.92(m,1H),3.81(s,3H),3.70(m,1H),3.64(m,2H),3.62(t,2H),3.28(m,1H)。
(3-p-methoxy-phenyl)-4-(2-mannoside base oxethyl)-2(5
H)-furanone (61)
Mp?146-148℃;EIMS?m/z:412[M
+];IR(KBr)cm
-1:1665(C=O),3376(OH);
1H?NMR(DMSO-
d 6)δppm:7.58(d,2H),6.94(d,1H),6.82(m,2H),4.91(s,2H),4.56(d,1H),4.18(t,2H),4.01(m,1H),3.97(m,1H),3.84(s,3H),3.75(m,1H),3.73(m,2H),3.61(t,2H),3.13(m,1H)。
(3-p-methoxy-phenyl)-4-(2-idose glycosides base oxethyl)-2(5
H)-furanone (62)
Mp?166-168℃;EIMS?m/z:412[M
+];IR(KBr)cm
-1:1589(C=O),3365(OH);
1H?NMR(DMSO-
d 6)δppm:7.63(d,2H),6.98(d,H),6.82(m,2H),4.98(s,2H),4.41(d,1H),4.12(t,2H),4.03(m,1H),3.98(m,1H),3.82(s,3H),3.78(m,1H),3.65(m,2H),3.54(t,2H),3.27(m,1H)。
(3-p-methoxy-phenyl)-4-(2-talose glycosides base oxethyl)-2(5
H)-furanone (63)
Mp?130-132℃;EIMS?m/z:412[M
+];IR(KBr)cm
-1:1750(C=O),3349(OH);
1H?NMR(DMSO-
d 6)δppm:7.65(d,2H),6.92(d,H),6.84(m,2H),4.89(s,2H),4.36(d,1H),4.16(t,2H),4.12(m,1H),3.98(m,1H),3.87(s,3H),3.75(m,1H),3.70(m,2H),3.55(t,2H),3.13(m,1H)。
(3-p-methoxy-phenyl)-4-(2-Arabinoside base oxethyl)-2(5
H)-furanone (64)
Mp?143-145℃;EIMS?m/z:382[M
+];IR(KBr)cm
-1:1579(C=O),3468(OH);
1H?NMR(DMSO-
d 6)δppm:7.46(d,2H),6.87(d,H),6.80(m,2H),5.27(d,H),4.92(s,2H),4.67(d,1H),4.30(t,1H),4.21(t,2H),3.87(s,3H),3.75(m,2H),3.69(t,2H),3.53(m,1H),3.43(t,1H),3.21(m,1H),3.04(m,1H)。
(3-p-methoxy-phenyl)-4-(2-lyxoside base oxethyl)-2(5
H)-furanone (65)
Mp?152-154℃;EIMS?m/z:382[M
+];IR(KBr)cm
-1:1655(C=O),3356(OH);
1H?NMR(DMSO-
d 6)δppm:7.66(d,2H),6.91(d,H),6.85(m,2H),5.22(d,1H),4.96(s,2H),4.60(d,1H),4.34(t,1H),4.22(t,2H),3.84(s,3H),3.73(m,2H),3.70(t,2H),3.49(m,1H),3.40(t,1H),3.28(m,1H),3.02(m,1H)。
(3-p-methoxy-phenyl)-4-(2-rhamnoside base oxethyl)-2(5
H)-furanone (66)
Mp?142-143℃;EIMS?m/z:332[M
+];IR(KBr)cm
-1:1780(C=O),3458(OH);
1H?NMR(DMSO-
d 6)δppm:7.43(d,2H),6.96(d,H),6.82(m,2H),4.98(s,2H),4.40(d,1H),4.23(t,2H),4.02(m,1H),3.99(m,1H),3.84(s,3H),3.75(m,1H),3.71(m,2H),3.62(t,2H),3.28(m,1H)。
(3-chloro-phenyl-)-4-(2-(4-methylpiperazine-1-yl) oxyethyl group)-2(5
H)-furanone (67)
Mp?160-163℃;EIMS?m/z:386[M
+];IR(KBr)cm
-1:1693(C=O),3587(NH);
1H?NMR(CDCl
3)δppm:7.58(d,2H),6.96(d,1H),6.80(m,2H),4.90(s,2H),4.33(t,2H),3.56(t,4H),3.26(s,3H),2.74(t,2H),2.48(t,4H)。
(3-chloro-phenyl-)-4-(2-(4-oil of mirbane diazanyl) oxyethyl group)-2(5
H)-furanone (68)
Mp?154-157℃;EIMS?m/z:389[M
+];IR(KBr)cm
-1:1688(C=O),3642(NH);
1H?NMR(CDCl
3)δppm:8.14(d,2H),7.58(d,2H),7.13(d,2H),6.94(d,1H),6.72(m,2H),4.96(s,2H),4.32(t,2H),4.01(s,H),3.44(t,2H),2.58(s,H)。
(3-chloro-phenyl-)-4-(2-benzyl amino ethoxy)-2(5
H)-furanone (69)
Mp?160-162℃;EIMS?m/z:343[M
+];IR(KBr)cm
-1:1677(C=O),3578(NH);
1H?NMR(CDCl
3)δppm:7.57(d,2H),7.23(s,1H),7.15(d,2H),6.95(m,2H),6.69(t,1H),4.94(s,2H),4.21(t,2H),3.75(s,2H),2.91(t,2H),2.36(s,H)。
(3-chloro-phenyl-)-4-[2-(piperazine-1-yl) oxyethyl group]-2(5
H)-furanone (70)
Mp?157-159℃;EIMS?m/z:322[M
+];IR(KBr)cm
-1:1588(C=O),3470(NH);
1H?NMR(CDCl
3)δppm:7.45(d,2H),6.92(d,1H),6.83(m,2H),5.38(s,1H),4.90(s,2H),4.24(t,2H),3.36(t,2H),2.61(t,4H),2.34(t,4H),1.98(d,1H)。
(3-chloro-phenyl-)-4-(2-altrose glycosides base oxethyl)-2(5
H)-furanone (71)
Mp?162-165℃;EIMS?m/z:416[M
+];IR(KBr)cm
-1:1649(C=O),3566(OH);
1H?NMR(DMSO-
d 6)δppm:7.58(d,2H),6.94(d,1H),6.80(m,2H),4.98(s,2H),4.60(d,1H),4.28(t,2H),4.05(m,1H),3.94(m,1H),3.86(m,1H),3.80(m,2H),3.61(t,2H),3.58(m,1H)。
(3-chloro-phenyl-)-4-(2-mannoside base oxethyl)-2(5
H)-furanone (72)
Mp?151-153℃;EIMS?m/z:416[M
+];IR(KBr)cm
-1:1774(C=O),3478(OH);
1H?NMR(DMSO-
d 6)δppm:7.53(d,2H),6.88(d,1H),6.84(m,2H),4.86(s,2H),4.54(d,1H),4.28(t,2H),4.12(m,1H),3.96(m,1H),3.83(m,1H),3.76-3.80(m,2H),3.68(t,2H),3.55(m,1H)。
(3-chloro-phenyl-)-4-(2-idose glycosides base oxethyl)-2(5
H)-furanone (73)
Mp?153-155℃;EIMS?m/z:416[M
+];IR(KBr)cm
-1:1659(C=O),3305(OH);
1H?NMR(DMSO-
d 6)δppm:7.67(d,2H),6.85(d,1H),6.80(m,2H),4.94(s,2H),4.52(d,1H),4.21(t,2H),4.12(m,1H),3.94(m,1H),3.88(m,1H),3.72-3.86(m,2H),3.69(t,2H),3.48(m,1H)。
(3-chloro-phenyl-)-4-(2-talose glycosides base oxethyl)-2(5
H)-furanone (74)
Mp?169-171℃;EIMS?m/z:416[M
+];IR(KBr)cm
-1:1646(C=O),3364(OH);
1H?NMR(DMSO-
d 6)δppm:7.66(d,2H),6.98(d,1H),6.86(m,2H),4.92(s,2H),4.48(d,1H),4.21(t,2H),4.11(m,1H),3.96(m,1H),3.76(m,1H),3.74(m,2H),3.68(t,2H),3.51(m,1H)。
(3-chloro-phenyl-)-4-(2-Arabinoside base oxethyl)-2(5
H)-furanone (75)
Mp?167-170℃;EIMS?m/z:386[M
+];IR(KBr)cm
-1:1556(C=O),3280(OH);
1H?NMR(DMSO-
d 6)δppm:7.58(d,2H),6.96(d,1H),6.80(m,2H),5.25(d,H),4.94(s,2H),4.56(d,1H),4.48(t,1H),4.23(t,2H),3.76-3.85(m,2H),3.74(t,2H),3.65(m,1H),3.59(t,1H),3.46(m,1H),3.39(m,1H)。
(3-chloro-phenyl-)-4-(2-lyxoside base oxethyl)-2(5
H)-furanone (76)
Mp?147-149℃;EIMS?m/z:386[M
+];IR(KBr)cm
-1:1690(C=O),3424(OH);
1H?NMR(DMSO-
d 6)δppm:7.58(d,2H),6.96(d,1H),6.83(m,2H),5.28(d,1H),4.99(s,2H),4.52(d,1H),4.46(t,1H),4.11(t,2H),3.75-3.80(m,2H),3.72(t,2H),3.58(m,1H),3.52(t,1H),3.48(m,1H),3.29(m,1H)。
(3-chloro-phenyl-)-4-(2-rhamnoside base oxethyl)-2(5
H)-furanone (77)
Mp?149-152℃;EIMS?m/z:326[M
+];IR(KBr)cm
-1:1711(C=O),3340(OH);
1H?NMR(DMSO-
d 6)δppm:7.67(d,2H),6.95(d,1H),6.81(m,2H),5.48(d,1H),4.97(s,2H),4.57(d,1H),4.48(t,1H),4.24(t,2H),3.78-3.80(m,2H),3.75(t,2H),3.64(m,1H),3.56(t,1H),3.48(m,1H),3.42(m,1H)。
(3-nitrophenyl)-4-(2-(4-methylpiperazine-1-yl) oxyethyl group)-2(5
H)-furanone (78)
Mp?160-163℃;EIMS?m/z:397[M
+];IR(KBr)cm
-1:1680(C=O);
1H?NMR(CDCl
3)δppm:7.78(d,2H),6.91(d,1H),6.80(m,2H),4.93(s,2H),4.39(t,2H),3.62(t,4H),3.27(s,3H),2.74(t,2H),2.35(t,4H)。
(3-nitrophenyl)-4-(2-(4-oil of mirbane diazanyl) oxyethyl group)-2(5
H)-furanone (79)
Mp?144-147℃;EIMS?m/z:400[M
+];IR(KBr)cm
-1:1698(C=O),3564(NH);
1H?NMR(CDCl
3)δppm:7.92(d,2H),7.36(d,2H),7.09(d,2H),6.88(d,1H),6.78(m,2H),4.95(s,2H),4.39(t,2H),4.05(s,1H),3.04(t,2H),2.82(s,1H)。
(3-nitrophenyl)-4-(2-benzyl amino ethoxy)-2(5
H)-furanone (80)
Mp?173-175℃;EIMS?m/z:354[M
+];IR(KBr)cm
-1:1569(C=O),3665(NH);
1H?NMR(CDCl
3)δppm:7.56(d,2H),7.21(t,H),7.05(d,2H),6.95(d,1H),6.80(m,2H),4.97(s,2H),4.28(t,2H),3.75(s,2H),2.98(t,2H),2.17(s,H)。
(3-nitrophenyl)-4-[(2-(piperazine-1-yl) oxyethyl group)-2(5
H)-furanone (81)
Mp?165-168℃;EIMS?m/z:333[M
+];IR(KBr)cm
-1:1647(C=O),3546(NH);
1H?NMR(CDCl
3)δppm:7.36(d,2H),6.91(d,1H),6.82(m,2H),5.34(s,1H),4.90(s,2H),4.26(t,2H),3.04(t,2H),2.68(t,4H),2.39(t,4H),1.65(d,1H)。
(3-nitrophenyl)-4-(2-altrose glycosides base oxethyl)-2(5
H)-furanone (82)
Mp?154-157℃;EIMS?m/z:427[M
+];IR(KBr)cm
-1:1570(C=O),3340(OH);
1H?NMR(DMSO-
d 6)δppm:7.59(d,2H),7.01(d,1H),6.85(m,2H),4.92(s,2H),4.58(d,1H),4.33(t,2H),4.18(m,1H),3.94(m,1H),3.82(m,1H),3.77(m,2H),3.72(t,2H),3.61(m,1H)。
(3-nitrophenyl)-4-(2-mannoside base oxethyl)-2(5
H)-furanone (83)
Mp?168-171℃;EIMS?m/z:427[M
+];IR(KBr)cm
-1:1459(C=O),3280(OH);
1H?NMR(DMSO-
d 6)δppm:7.45(d,2H),6.93(d,1H),6.80(m,2H),4.92(s,2H),4.54(d,1H),4.23(t,2H),4.12(m,1H),3.94(m,1H),3.84(m,1H),3.78-3.80(m,2H),3.74(t,2H),3.66(m,1H)。
(3-nitrophenyl)-4-(2-idose glycosides base oxethyl)-2(5
H)-furanone (84)
Mp?162-165℃;EIMS?m/z:427[M
+];IR(KBr)cm
-1:1450(C=O),3423(OH);
1H?NMR(DMSO-
d 6)δppm:7.52(d,2H),6.93(d,1H),6.87(m,2H),4.92(s,2H),4.58(d,1H),4.27(t,2H),4.15(m,1H),3.96(m,1H),3.83(m,1H),3.75-3.80(m,2H),3.72(t,2H),3.52(m,1H)。
(3-nitrophenyl)-4-(2-talose glycosides base oxethyl)-2(5
H)-furanone (85)
Mp?148-151℃;EIMS?m/z:427[M
+];IR(KBr)cm
-1:1677(C=O),3344(OH);
1H?NMR(DMSO-
d 6)δppm:7.49(d,2H),6.96(d,1H),6.83(m,2H),4.94(s,2H),4.55(d,1H),4.26(t,2H),4.13(m,1H),3.97(m,1H),3.85(m,1H),3.77(m,2H),3.55(t,2H),3.43(m,1H)。
(3-nitrophenyl)-4-(2-Arabinoside base oxethyl)-2(5
H)-furanone (86)
Mp?174-177℃;EIMS?m/z:397[M
+];IR(KBr)cm
-1:1686(C=O),3470(OH);
1H?NMR(DMSO-
d 6)δppm:7.57(d,2H),6.92(d,1H),6.68(m,2H),5.20(d,1H),4.93(s,2H),4.54(d,1H),4.43(t,1H),4.23(t,2H),3.76(m,2H),3.72(t,2H),3.68(m,1H),3.52(t,1H),3.44(m,1H),3.17(m,1H)。
(3-nitrophenyl)-4-(2-lyxoside base oxethyl)-2(5
H)-furanone (87)
Mp?179-182℃;EIMS?m/z:397[M
+];IR(KBr)cm
-1:1590(C=O),3325(OH);
1H?NMR(DMSO-
d 6)δppm:7.67(d,2H),6.85(d,1H),6.72(m,2H),5.19(d,1H),4.92(s,2H),4.55(d,1H),4.48(t,1H),4.15(t,2H),3.86(m,2H),3.75(t,2H),3.63(m,1H),3.55(t,1H),3.38(m,1H),3.19(m,1H)。
(3-nitrophenyl)-4-(2-rhamnoside base oxethyl)-2(5
H)-furanone (88)
Mp?175-177℃;EIMS?m/z:358[M
+];IR(KBr)cm
-1:1711(C=O),3360(OH);
1H?NMR(DMSO-
d 6)δppm:7.49(d,2H),6.79(d,1H),6.65(m,2H),5.96(s,2H),4.58(d,1H),4.24(t,2H),4.14(m,1H),3.99(m,1H),3.82(m,1H),3.71(m,2H),3.53(t,2H),3.42(m,1H)?。
Claims (4)
1. a class 3-aryl-4-(2-glycosyl/amino ethoxy)-2 (5H)-furanone type compounds is characterized in that they have following general structure
R in the formula (I)
1, R
2, R
3, R
4And R
5Definition take from following two groups the definition one of:
(1) R
1=R
2=R
4=H; R
3=Br, OH, F, NO
2Or NH
2 Azloglycoside base, glucoside base, gulose glycosides base, galactoside base, riboside base, xyloside base or sorb glycosyl;
2. a method for preparing 3-aryl-4-claimed in claim 1 (2-amino ethoxy)-2 (5H)-furanone type compounds is characterized in that it comprises the following steps:
Step 1. is with 2-R
1-3-R
2-4-R
3-5-R
4Substituted phenylacetic acid and sodium ethylate are dissolved in the dehydrated alcohol, at room temperature add ethyl bromoacetate, are warming up between 40-50 ℃ and react 5-10h, and the ratio of its amount of substance is: 2-R
1-3-R
2-4-R
3-5-R
4Substituted phenylacetic acid: sodium ethylate: ethyl bromoacetate=1: 3: 2, react complete, suction filtration, concentrated, the ether dilution, washing, the organic layer saturated common salt is washed to neutrality, dry, concentrated, use silica gel column chromatography, eluent is sherwood oil-AcOEt, the volume ratio of sherwood oil and AcOEt is 20: 1-5: 1, obtain 2-(2-R
1-3-R
2-4-R
3-5-R
4Phenylacetyl oxygen base) ethyl acetate (II),
Step 2. at room temperature joins NaH in the anhydrous tetrahydro furan, then splashes into 2-(2-R
1-3-R
2-4-R
3-5-R
4Phenylacetyl oxygen base) anhydrous tetrahydrofuran solution of ethyl acetate (II), dropwise under room temperature and react 2-7h, the ratio of amount of substance is: II: NaH=1: 1, react complete, pour in the frozen water, use extracted with diethyl ether, the water layer acidifying, separate out precipitation, suction filtration gets white to faint yellow solid 4-hydroxyl-3 (2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2 (5H)-furanone (III);
Step 3. is with 4-hydroxyl-3 (2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2 (5H)-furanone (III), glycol dibromide and triethylamine are dissolved in the anhydrous propanone, and the ratio of its amount is 4-hydroxyl-3 (2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2 (5H)-furanone (III): glycol dibromide: triethylamine=1: 3: 2, backflow 4-10h, react complete after, add water, ethyl acetate extraction, organic layer are used respectively saturated NaHCO
3Solution and saturated common salt water washing, anhydrous MgSO
4Drying concentrates to get product 4-bromine oxethyl-3 (2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2 (5H)-furanone (IV), with IV, R
5-H and triethylamine are dissolved among the DMF, and the ratio of amount of substance is: IV: R
5-H: triethylamine=1: (1-4): (2-10), react 8-10h under 50 ℃ of conditions, thin up, ethyl acetate extraction, organic layer is washed to neutrality with saturated common salt, uses anhydrous MgSO
4Drying, concentrated, through column chromatography purification, get 3-aryl-4-(2-amino ethoxy)-2 (5H)-furanone type compounds (I), eluent is chloroform-methanol, and its volume ratio is (100: 1)-(20: 1), and adds the triethylamine of 2-5%;
3. method for preparing 3-aryl-4-claimed in claim 1 (2-glycosyl oxyethyl group)-2 (5H)-furanone type compounds is characterized in that: it is that the step 3 among the described preparation method of claim 2 is substituted with following steps 3 ':
Step 3 '. the Amberlite IR-120 that will be equivalent to saccharic amount 4-7% joins in the ethylene bromohyrin, under 90 ℃ of conditions, reflux, disposable adding carbohydrate, continue to reflux, wherein the ratio of amount of substance is: ethylene bromohyrin: carbohydrate=20: 1, then filter, filter residue washs with ethylene bromohyrin, the ethylene bromohyrin that pressure reducing and steaming is excessive gets thick crude product bromotrifluoromethane glucosides (V), not purifiedly is directly used in next step reaction;
Bromotrifluoromethane glucosides (V) is dissolved in dry DMF, adds again triethylamine and 4-hydroxyl-3 (2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2 (5H)-furanone (III), the ratio of amount of substance is: bromotrifluoromethane glucosides (V): triethylamine: 4-hydroxyl-3-(2-R
1-3-R
2-4-R
3-5-R
4Phenyl)-2 (5H)-furanone (III)=(1-3): 1: (2-10), be warming up to 50 ℃, reaction 6-10h, react complete after, in flask, add entry, usefulness ethyl acetate extraction 3 times, salt solution is washed till neutrality, anhydrous MgSO
4Drying is filtered, and is concentrated, through column chromatography purification, and developping agent condition: CH
3OH: CHCl
3=1: (20-80), obtain 3-aryl-4-(2-glycosyl oxyethyl group)-2 (5H)-furanone type compounds (I);
In step 3 ' in, R
1, R
2, R
3, R
4And R
5Be defined as R
1=R
2=R
3=H, R
4=OCH
3, Cl or NO
2, R
5=altrose glycosides base, mannoside base, idose glycosides base, talose glycosides base, Arabinoside base, lyxoside base or rhamnoside base.
4. the application of 3-aryl-4-claimed in claim 1 (2-glycosyl/amino ethoxy)-2 (5H)-furanone type compounds in the preparation anti-infectives.
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Title |
---|
Aurelie Mallinger et al.,.3-Aryltetronic Acids:Efficient Preparation and Use as Precursors for Vulpinic Acids.《The Journal of Organic Chemistry》.2008,第74卷(第3期),1124-1129. * |
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