CN106008652B - Enoxolone isopentane amide derivatives and its preparation method and application - Google Patents
Enoxolone isopentane amide derivatives and its preparation method and application Download PDFInfo
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- XEVBRXZNHMNVNW-RLBZZRBJSA-N CCCC[C@@](C)([C@](C)(CC1)C2[C@@](C)(CC3)[C@@H]1C(C)(C)[C@H]3O)C([C@H](CCC1)C[C@@]1(C)C(O)=O)=CC2=N Chemical compound CCCC[C@@](C)([C@](C)(CC1)C2[C@@](C)(CC3)[C@@H]1C(C)(C)[C@H]3O)C([C@H](CCC1)C[C@@]1(C)C(O)=O)=CC2=N XEVBRXZNHMNVNW-RLBZZRBJSA-N 0.000 description 1
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Abstract
The invention discloses a kind of enoxolone isopentane amide derivatives and its preparation method and application.The enoxolone isopentane amide derivatives have formula (III) structure.The preparation method includes: in (1) organic solvent, and enoxolone is reacted with halogenated isopentane, obtains formula (II) compound；(2) in organic solvent, formula (II) compound is reacted with aniline or substituted aniline, obtains the enoxolone isopentane amide derivatives.Invention additionally discloses the applications of the derivative.Novel enoxolone isopentane amide derivatives of the invention significantly inhibit bacterium, can be applied to preparation antibacterials.
Description
Technical field
The present invention relates to chemical syntheses, more particularly to a kind of novel enoxolone isopentane amide derivatives and its preparation
Method and the purposes as antibacterials.
Background technique
Radix Glycyrrhizae is a kind of common Chinese herbal medicine, it is widely distributed in the northwest, southwest and northeast in China, shares eight product
Kind.Its effective component is glycyrrhizic acid and glycyrrhetate substance, and enoxolone is that glycyrrhizic acid is hydrolyzed through gastric acid or through β-in liver
One of the active constituent that glycuronidase is decomposed to form, it have antiviral and antitumor, anti-inflammatory, antibacterial, anti-cardiovascular disease,
Various bioactivity and the pharmacological activity such as anti-oxidant, protection liver cell, immunological regulation and adrenocortical hormones fuction.
The pharmacological action of glycyrrhizic acid is substantially the effectiveness of enoxolone.
As long as amide refers to a kind of organic compound with amido bond after carboxyl and amino condensation, usual amides chemical combination
Object is condensed by amino and carboxyl.Therefore the structure of enoxolone is modified, synthesizing amide analog derivative enhances it
Bacterium activity, is meaningful project.
Summary of the invention
Goal of the invention: the present invention provides a kind of enoxolone isopentane amide derivatives with antibacterial effect, originally
Another purpose of invention is to provide preparation method and use.
A kind of enoxolone isopentane amide derivatives, it has following general formula:
In formula (III),For by least one methoxy-substituted phenyl.
Further,For by 1~2 methoxy-substituted phenyl.
Further,For
The present invention also provides the preparation methods of the enoxolone isopentane amide derivatives, comprising:
(1) in organic solvent, enoxolone is reacted with halogenated isopentane, obtains formula (II) compound；
(2) in organic solvent, formula (II) compound is reacted with aniline or substituted aniline, obtains the enoxolone isopentane
Amide derivatives；
The present invention, which is reacted using enoxolone with halogenated isopentane, generates enoxolone isopentane, improves the rouge of product
Dissolubility is more advantageous to absorption of human body；Amides corresponding with aniline or substituted aniline reaction production spread out enoxolone isopentane again
Biology achievees the purpose that improve antibacterial activity.
In step (1), organic solvent DMF.Reaction temperature is 60~80 DEG C, and the reaction time is 5~8h.
The halogenated isopentane is bromo isopentane, chloro isopentane or fluoro isopentane.
In step (2), organic solvent is methylene chloride.Reaction temperature is 20~30 DEG C, and the reaction time is 12~16h.
In step (2), reaction system also contains EDC and HOBT.
The present invention also provides the application of the enoxolone isopentane amide derivatives in medicine preparation.
The present invention also provides a kind of drugs, including the enoxolone isopentane amide derivatives.
Using a effective amount of enoxolone isopentane amide derivatives as active constituent, pharmaceutically acceptable load is added
Body can be prepared into corresponding drug.
The drug is anti-bacterial drug.Bacterium can be Gram-negative bacteria or gram-positive bacteria, specially greatly
Enterobacteria, staphylococcus aureus, bacillus subtilis, pseudomonas aeruginosa etc..
Compared with prior art, the beneficial effect comprise that
The experimental results showed that novel enoxolone isopentane amide derivatives of the invention have apparent suppression to bacterium
Production is used.Therefore enoxolone isopentane amide derivatives of the invention can be applied to preparation antibacterials.
Specific embodiment
The present invention is explained in more detail below with reference to embodiment, the embodiment of the present invention is merely to illustrate skill of the invention
Art scheme, the scope of the present invention is not by any restrictions of these examples.
EDC:1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride
HOBT:1- hydroxybenzotriazole
EA: ethyl acetate
DMSO: dimethyl sulfoxide
DMF: dimethylformamide
The preparation of 1 enoxolone isopentane anilide (compound 1) of embodiment
The structure of compound 1 are as follows:
Step (1): 4.7g enoxolone (shown in formula (I)) and 1.25ml bromo isopentane are added in 20ml DMF
(CAS:107-82-4), 80 DEG C of heating reflux reaction 5h.After reaction, contact plate is sampled, EA extraction is depressurized after organic phase washing
Distill to obtain white solid enoxolone isoamyl alkyl ester (shown in formula (II)).
Step (2): 1.2mmol EDC, 1.2mmol HOBT are added in 6ml methylene chloride, are added after 28 DEG C of activation 30min
Enter 1mmol enoxolone isoamyl alkyl ester, 1mmol aniline is added and is dissolved into 10ml methylene chloride, under room temperature (generally 25 DEG C)
It reacts overnight (generally 12h), EA extraction, organic phase carries out silica gel column chromatography, EA: petroleum ether=1:15 is rinsed, and collects outflow
Liquid, vacuum distillation obtain white solid, filter, dry, obtain target compound.
Yield 95%, Mp:174-176 DEG C of1H NMR(DMSO,300MHz),9.98(s,1H,NH),8.42(s,1H,
), CH 7.85-7.83 (d, J=6.06Hz, 1H, ArH), 7.68-7.62 (d, J=1.23Hz, 1H, ArH), 7.38-7.32 (m,
3H,ArH),5.56(s,1H,CH),3.47(m,2H,CH2),3.32(m,1H,CH),2.01(m,3H,CH),1.85-1.92(m,
8H,CH2),1.55-1.67(m,10H,CH2),1.29(s,3H,CH3),1.10(s,3H,CH3), 1.05 (s, 3H, CH3), 0.93
(m,2H,CH2),0.98(s,6H,CH3)0.88(s,3H,CH3), 0.85 (s, 3H, CH3), 0.66 (s, 3H, CH3), 0.67 (s,
3H,CH3) .MS (ESI): 615.94 (C41H61NO3, [M+H]+) and .Anal.Calcd for C41H61NO3: C, 79.95；H,9.98；
N, 2.27%.Found:C, 79.63；H,9.93；N, 2.35%
The preparation of 2 enoxolone isopentane acyl neighbour methyl oxyaniline (compound 2) of embodiment
The structure of compound 2 are as follows:
The preparation method is the same as that of Example 1.Aniline is replaced with o-aminoanisole, obtains target compound.
White powder, yield 92%, Mp163-167 DEG C；1H NMR(DMSO,300MHz),9.98(s,1H,NH),8.42
(s, 1H, CH), 7.68-7.62 (d, J=1.23Hz, 1H, ArH), 7.38-7.32 (m, 3H, ArH), 5.56 (s, 1H, CH),
3.65(s,3H,OCH3),3.47(m,2H,CH2),3.32(m,1H,CH),2.01(m,3H,CH),1.85-1.92(m,8H,
CH2),1.55-1.67(m,10H,CH2),1.29(s,3H,CH3),1.10(s,3H,CH3), 1.05 (s, 3H, CH3), 0.93 (m,
2H,CH2),0.98(s,6H,CH3)0.88(s,3H,CH3), 0.85 (s, 3H, CH3), 0.66 (s, 3H, CH3), 0.67 (s, 3H,
CH3) .MS (ESI): 645.97 (C42H63NO4, [M+H]+) and .Anal.Calcd for C42H63NO4: C, 78.09；H,9.83；N,
2.17%.Found:C, 78.48；H,9.93；N, 2.46%
The preparation of methyl oxyaniline (compound 3) between 3 enoxolone isopentane acyl of embodiment
The structure of compound 3 are as follows:
The preparation method is the same as that of Example 1, replaces aniline with m-anisidine, obtains target compound.
White powder, yield 91%, Mp194-196 DEG C；1H NMR(DMSO,300MHz),9.98(s,1H,NH),8.42
(s, 1H, CH), 7.85-7.83 (d, J=6.06Hz, 1H, ArH), 7.68-7.62 (d, J=1.23Hz, 1H, ArH), 7.38-
7.32(m,2H,ArH),5.56(s,1H,CH),3.72(s,3H,OCH3),3.47(m,2H,CH2),3.32(m,1H,CH),2.01
(m,3H,CH),1.85-1.92(m,8H,CH2),1.55-1.67(m,10H,CH2),1.29(s,3H,CH3),1.10(s,3H,
CH3), 1.05 (s, 3H, CH3), 0.93 (m, 2H, CH2),0.98(s,6H,CH3)0.88(s,3H,CH3), 0.85 (s, 3H, CH3),
0.66(s,3H,CH3), 0.67 (s, 3H, CH3) .MS (ESI): 645.97 (C42H63NO4, [M+H]+) and .Anal.Calcd for
C42H63NO4:C,78.09；H,9.83；N, 2.17%.Found:C, 78.52；H,9.68；N, 2.03%
Preparation of the 4 enoxolone isopentane acyl of embodiment to methyl oxyaniline (compound 4)
The structure of compound 4 are as follows:
The preparation method is the same as that of Example 1, replaces aniline with P-nethoxyaniline, obtains target compound.
White powder, yield 94%, Mp168-170 DEG C；1H NMR(DMSO,300MHz),9.98(s,1H,NH),8.42
(s, 1H, CH), 7.85-7.83 (d, J=6.06Hz, 1H, ArH), 7.68-7.62 (d, J=1.23Hz, 1H, ArH), 7.38-
7.32(m,2H,ArH),5.56(s,1H,CH),3.58(s,3H,OCH3),3.47(m,2H,CH2),3.32(m,1H,CH),2.01
(m,3H,CH),1.85-1.92(m,8H,CH2),1.55-1.67(m,10H,CH2),1.29(s,3H,CH3),1.10(s,3H,
CH3), 1.05 (s, 3H, CH3), 0.93 (m, 2H, CH2),0.98(s,6H,CH3)0.88(s,3H,CH3), 0.85 (s, 3H, CH3),
0.66(s,3H,CH3), 0.67 (s, 3H, CH3) .MS (ESI:645.97 (C42H63NO4, [M+H]+) and .Anal.Calcd for
C42H63NO4:C,78.09；H,9.83；N, 2.17%.Found:C, 78.56；H,9.23；N, 2.08%.
The preparation of 5 enoxolone isopentane acyl of embodiment-(2,6- dimethoxy)-aniline (compound 5)
The structure of compound 5 are as follows:
The preparation method is the same as that of Example 1, replaces aniline with 2,6- dimethoxyaniline, obtains target compound.
White powder, yield 92%, Mp153-156 DEG C；1H NMR(DMSO,300MHz),9.98(s,1H,NH),8.42
(s,1H,CH),7.38-7.32(m,3H,ArH),5.56(s,1H,CH),3.68(s,6H,OCH3),3.47(m,2H,CH2),
3.32(m,1H,CH),2.01(m,3H,CH),1.85-1.92(m,8H,CH2),1.55-1.67(m,10H,CH2),1.29(s,
3H,CH3),1.10(s,3H,CH3), 1.05 (s, 3H, CH3), 0.93 (m, 2H, CH2),0.98(s,6H,CH3)0.88(s,3H,
CH3), 0.85 (s, 3H, CH3), 0.66 (s, 3H, CH3), 0.67 (s, 3H, CH3) .MS (ESI:676.00 (C43H65NO5, [M+H]
+).Anal.Calcd for C43H65NO5:C,76.40；H,9.69；N, 2.07%.Found:C, 76.57；H,9.86；N,
2.08%.
The preparation of 6 enoxolone isopentane acyl of embodiment-(2,4- dimethoxy)-aniline (compound 6)
The structure of compound 6 are as follows:
The preparation method is the same as that of Example 1, replaces aniline with 2,4- dimethoxyaniline, obtains target compound.
White powder, yield 92%, Mp147-146 DEG C；1H NMR(DMSO,300MHz),9.98(s,1H,NH),8.42
(s, 1H, CH), 7.68-7.62 (d, J=1.23Hz, 1H, ArH), 7.38-7.32 (m, 2H, ArH), 5.56 (s, 1H, CH),
3.61(s,6H,OCH3),3.47(m,2H,CH2),3.32(m,1H,CH),2.01(m,3H,CH),1.85-1.92(m,8H,
CH2),1.55-1.67(m,10H,CH2),1.29(s,3H,CH3),1.10(s,3H,CH3), 1.05 (s, 3H, CH3), 0.93 (m,
2H,CH2),0.98(s,6H,CH3)0.88(s,3H,CH3), 0.85 (s, 3H, CH3), 0.66 (s, 3H, CH3), 0.67 (s, 3H,
CH3) .MS (ESI:676.00 (C43H65NO5, [M+H]+) and .Anal.Calcd for C43H65NO5:C,76.40；H,9.69；N,
2.07%.Found:C, 76.57；H,9.86；N, 2.08%.
The preparation of 7 enoxolone isopentane acyl of embodiment-(2,3- dimethoxy)-aniline (compound 7)
The structure of compound 7 are as follows:
The preparation method is the same as that of Example 1, replaces aniline with 2,3- dimethoxyaniline, obtains target compound.
White powder, yield 92%, Mp155-157 DEG C；1H NMR(DMSO,300MHz),9.98(s,1H,NH),8.42
(s, 1H, CH), 7.68-7.62 (d, J=1.23Hz, 1H, ArH), 7.38-7.32 (m, 2H, ArH), 5.56 (s, 1H, CH),
3.72(s,6H,OCH3),3.47(m,2H,CH2),3.32(m,1H,CH),2.01(m,3H,CH),1.85-1.92(m,8H,
CH2),1.55-1.67(m,10H,CH2),1.29(s,3H,CH3),1.10(s,3H,CH3), 1.05 (s, 3H, CH3), 0.93 (m,
2H,CH2),0.98(s,6H,CH3)0.88(s,3H,CH3), 0.85 (s, 3H, CH3), 0.66 (s, 3H, CH3), 0.67 (s, 3H,
CH3) .MS (ESI:676.00 (C43H65NO5, [M+H]+) and .Anal.Calcd for C43H65NO5:C,76.40；H,9.69；N,
2.07%.Found:C, 76.57；H,9.86；N, 2.08%.
The research of 8 enoxolone isopentane amide derivatives antibacterial activity of embodiment
1. experimental material and method
1.1 drugs and reagent
Mueller-Hinton culture medium (beef extract powder 5g, casein hydrolysate 17.5g, starch 1.5g, agar 12.5g,
Be added 1000mL distilled water in), chloramphenicol, penicillin, DMSO, MTT (3- (4,5- dimethylthiazole -2) -2, four nitrogen of-diphenyl
Azoles bromide, trade name thiazolyl blue), isopropanol, hydrochloric acid, be analytical reagents, the compound 1-6 of synthesis, PBS buffer solution
(phosphate buffer 0.01mol/L, pH7.4, Na2HPO4.12H2O 2.9g, KH2PO40.2g, NaCl8.0g, KCl0.2g steam
Distilled water 1000mL).
1.2 strain
Escherichia coli (E.coli), staphylococcus aureus (S.aureus), bacillus subtilis (B.subtilis), copper
Green pseudomonad (P.aeruginosa)
1.3 experimental method
1.3.1 the preparation of culture medium
Beef extract powder 5g, casein hydrolysate 17.5g, starch 1.5g, agar 12.5g are taken, is added in 1000mL distilled water,
Heating boil dissolution, packing, 121 DEG C high pressure sterilization 15 minutes it is spare.
1.3.2 the culture of test organisms
In desinfection chamber, Escherichia coli, staphylococcus aureus, bacillus subtilis and four kinds of pseudomonas aeruginosa examinations are taken
Bacterial strain is tested, scrapes a small amount of inclined-plane lawn, use is a certain amount of respectively on four kinds of test strain inclined-planes with transfer needle under alcolhol burner
Bacteria suspension is made in sterile water, and a certain amount of be added to then is taken to melt and be cooled to 50 DEG C or so of MH culture medium (Mueller-
Hinton culture medium) in, it shakes up, pours into sterile petri dish at once, after being sealed after sufficiently condensing with rubber plug, cultivated in 37 DEG C
18-24h is spare.Bacterium solution 1mL is drawn, is diluted with MH culture medium by 1:1000, making bacterial concentration is about 105cfu/mL.
1.3.3 antibacterial experiment:
Candidate drug is dissolved in the solution that 2mg/mL is configured in DMSO, then with doubling dilution by chemicals dilating at one
Determine in concentration gradient (50 μ g/mL, 25 μ g/mL, 12.5pg/mL, 6.25 μ g/mL, 3.125 μ g/mL) and DMSO.It is micro in sterilizing
The culture medium of 100 μ L is separately added into titer plate first, Article 2 is positive control, and 100 μ L bacteria suspensions are added.Remaining hole
The drug solution of the middle bacteria suspension that 90 μ L are added and 10 μ L.Each drug solution concentration is 3 times parallel.It is marked in microtiter plate bottom
Bright bacteria name.For 24 hours in 37 DEG C of cultures by the culture dish handled, observation.
1.3.4 the measurement of MIC
After each microtiter plate can intuitively measure its MIC value, 50 μ L are added in each hole of plate
PBS buffer solution (phosphate buffer 0.01mol/L, pH7.4, Na2HPO4.2H2O2.9g, KH2PO40.2g, NaCl8.0g,
KCl0.2g, distilled water 1000mL), wherein including 2mg MTT/mL.Continue to be incubated for 4-5h at room temperature.Substance in hole is moved
Out and the isopropanol that 100 μ L contain 5%1mol/L HCl is added to extract dyestuff.Continue to assign at room temperature and educate 12h, in microplate reader
It measures each hole light absorption (OD value), measures wavelength 550nm.Drug is calculated according to each hole OD value, and dense is inhibited to the minimum of bacterial growth
Degree.
Minimum inhibitory concentration (minimum inhibitory concentration, MIC): it is incubated for 24 in certain circumstances
Hour, it can inhibit certain microorganism and the lowest concentration of drug to rise appreciably i.e. minimum inhibitory concentration occur, it is close according to the light of measurement
It spends (OD value), makes the standard curve of bacterial growth inhibiting rate, its corresponding drug concentration is acquired on standard curve.It measures
MIC is shown in Table 1
2. experimental result
Inhibition MIC value (μ g/mL) of the enoxolone isopentane amide derivatives listed by 1 present invention of table to bacterium
Control: chloramphenicol；Penicillin, enoxolone
The result shows that: enoxolone isopentane amide derivatives are to Escherichia coli, staphylococcus aureus, withered grass gemma
Bacillus, P. aeruginosa have different degrees of inhibiting effect, and the antibacterial effect of derivative is better than enoxolone.
Claims (8)
1. a kind of enoxolone isopentane amide derivatives, which is characterized in that it has following general formula:
In formula (III),
R is H, orFor
2. the preparation method of enoxolone isopentane amide derivatives according to claim 1, which is characterized in that packet
It includes:
(1) in organic solvent, enoxolone is reacted with halogenated isopentane, obtains formula (II) compound；
(2) in organic solvent, formula (II) compound is reacted with aniline or substituted aniline, obtains the enoxolone isopentane amide
Analog derivative；
。
3. preparation method according to claim 2, which is characterized in that in step (1), organic solvent DMF, reaction temperature
Degree is 60~80 DEG C, and the reaction time is 5~8h.
4. preparation method according to claim 2, which is characterized in that the halogenated isopentane is bromo isopentane, chlorine
For isopentane or fluoro isopentane.
5. preparation method according to claim 2, which is characterized in that in step (2), organic solvent is methylene chloride, instead
Answering temperature is 20~30 DEG C, and the reaction time is 12~16h.
6. preparation method according to claim 2, which is characterized in that in step (2), reaction system also contain EDC and
HOBT。
7. application of the enoxolone isopentane amide derivatives according to claim 1 in preparation antibacterials,
One or more of the anti-Escherichia coli of middle antibacterials, staphylococcus aureus, bacillus subtilis and pseudomonas aeruginosa.
8. a kind of antibacterials, which is characterized in that including enoxolone isopentane amide derivatives described in claim 1,
One or more of the anti-Escherichia coli of antibacterials, staphylococcus aureus, bacillus subtilis and pseudomonas aeruginosa.
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| Title |
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| SYNTHESIS OF SOME GLYCYRRHETIC ACID SULFONAMIDE DERIVATIVES WITH PROSPECTED ANTIMICROBIAL ACTIVITY;M. H. A. EL-GAMAL, et al.;《Qatar Univ. Sci. J.》;19941231;第14卷(第C期);147-153 * |
| 甘草次酸的化学修饰和结构改造研究进展;李斌等;《精细化工》;20060731;第23卷(第7期);643-648，691 * |
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