CN104892446A - Amide derivatives of linalool, preparation method of amide derivatives and application of amide derivatives in bacteria prevention - Google Patents
Amide derivatives of linalool, preparation method of amide derivatives and application of amide derivatives in bacteria prevention Download PDFInfo
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Abstract
The invention provides amide derivatives of linalool. The amide derivatives have a structural formula as shown in specification. The amide derivatives of linalool have obvious inhibiting effect on bacteria, and can be applied to preparation of antibacterial drugs.
Description
Technical field
The invention belongs to organic synthesis field, be specifically related to the application in a kind of amide derivatives of phantol and method for making thereof and its anti-microbial activity.
Background technology
Phantol is the alkene alcohols material that chain contains oxygen monoterpene derivative, and formal name used at school is linalool, and phantol is also known as Linaool, agalloch eaglewood oleyl alcohol, coriandrum alcohol, coriandrol etc.Phantol does not exist only in fragrant camphor tree, extensively exists in the plants such as coriander, lavandula angustifolia, jasmine, safflower green grass or young crops yet.Phantol has good anti-microbial activity, has research display phantol to have good restraining effect to intestinal bacteria, mouse salmonella typhi, listeria spp, Vibrio vulnificus etc.Experiment is had to show that the anti-microbial activity of phantol is 5 times of phenol.
Antibiotic drug resistance problems becomes the Important Problems that global medical aspect is paid close attention to already.The sudden change of bacterium result in it to antibiotic resistance, antibiotic abuse then accelerates the speed producing resistance, bacterium is made to create very strong resistance, make the good medicine of original germ resistance not reach the effect for the treatment of, thus develop the antibacterials with new texture extremely urgent.
Amides medicine also has good performance in germ resistance, there are some researches show that amides antibacterials are respiratory chain electron transmission by affecting pathogenic bacteria thus reach the growth suppressing pathogenic bacteria, finally reaches bacteriostatic action.Whether can modify the structure of phantol, form amide structure, thus strengthen its anti-microbial activity, be the problem that this area needs to solve.
Summary of the invention
Goal of the invention: for problems of the prior art, the invention provides the amide derivatives of the novel phantol of a class, provides preparation method and the purposes of this analog derivative simultaneously.
Technical scheme: the amide derivatives that the invention provides a kind of phantol, this material has following structural formula:
Wherein, R is:
The invention provides the preparation method of the amide derivatives of above-mentioned phantol, comprise the following steps:
Step 1: join in anhydrous DMF solution by phantol and salt of wormwood, drips the DMF solution of methyl bromoacetate after stirring, add water, extraction into ethyl acetate after reaction terminates, and then dry, recrystallization, obtains linalool methyl acetate;
Step 2: linalool methyl acetate is added in the aqueous solution of NaOH, after reflux, be extracted with ethyl acetate, stay aqueous phase, aqueous phase drips rare HCl solution, till precipitation does not increase, obtain linalool acetic acid;
Step 3: by 3,7-dimethyl-1,6-octadiene-3-alcohol acetic acid, I-hydroxybenzotriazole and 1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate is dissolved in methylene dichloride, anils is joined in reaction soln, reaction mixture reflux is after 8 hours, decompression steams methylene dichloride, and crude product obtains target compound through alcohol crystal.
More specifically, described step 1 is: join in anhydrous DMF solution by phantol and salt of wormwood, dropwise drips the DMF solution that concentration is 60% methyl bromoacetate after stirring at 0 ~ 5 DEG C, and reaction soln adds water in 50 ~ 70 DEG C of reactions after 7 ~ 9 hours, extraction into ethyl acetate 3 times, dry crude product.Crude product obtains linalool methyl acetate through alcohol crystal.
Described phantol and salt of wormwood add-on mole be 1:1, described phantol and methyl bromoacetate add-on mole be 1:1.
More specifically, described step 2 is: linalool methyl acetate being added concentration is in the aqueous solution of the NaOH of 10%, reflux 2 ~ 3h, then be extracted with ethyl acetate, stay aqueous phase, aqueous phase drips rare HCl solution, till precipitation does not increase, obtain linalool acetic acid.
More specifically, described step 3 is: 3,7-dimethyl-1,6-octadiene-3-alcohol acetic acid, I-hydroxybenzotriazole and 1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate dissolve and are in methylene dichloride, and joined by anils in reaction soln, reaction mixture reflux is after 7 ~ 9 hours, decompression steams methylene dichloride, and crude product obtains target compound through alcohol crystal.
Described linalool acetic acid, the mol ratio of I-hydroxybenzotriazole and 1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate is 1:1:1.
Described anils can select para-totuidine, meta-aminotoluene, to methyl oxyaniline, a methyl oxyaniline, para-fluoroaniline or m-fluoroaniline.
The present invention opens the application of the amide derivatives disclosing phantol, mainly uses it in antibacterials.
Beneficial effect: the novel amide derivatives containing phantol of the present invention has obvious restraining effect to bacterium.Therefore the amide derivatives containing phantol of the present invention can be applied to preparation antibacterials.
Embodiment:
Further describe the present invention by following examples, but scope of the present invention is not by any restriction of these embodiments.
Embodiment 1:
2-(linalool)-N-(to phenmethyl) ethanamide (compound 1)
Step 1: phantol 30.1 grams and 13.8 grams of salt of wormwood join in the anhydrous DMF solution of 100mL, dropwise drips the DMF solution of the 10mL of 15.2 grams of methyl bromoacetates at 0 DEG C after stirring.Reaction soln adds 300mL water, extraction into ethyl acetate 3 times in 60 DEG C of reactions after 8 hours, dry crude product.Crude product obtains linalool methyl acetate through alcohol crystal.
Step 2: add in the aqueous solution of 100mL10%NaOH by 20 grams of linalool methyl acetates, reflux 2h, extraction into ethyl acetate, stays aqueous phase.Aqueous phase drips rare HCl solution, till precipitation does not increase, obtains linalool acetic acid.
Step 3:21.2 g of compound C, 13.5 grams of HOBT (I-hydroxybenzotriazole) and 19.1 grams of EDCI (1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate) are dissolved in the methylene dichloride of 150mL, the para-totuidine of 100mmol joins in reaction soln, reaction mixture reflux is after 8 hours, decompression steams methylene dichloride, and crude product obtains target compound through alcohol crystal.
Gained compound is faint yellow.
1H NMR(DMSO,300MHz)δ:9.97(s,1H,NH),7.12(d,1H,J＝8.0Hz),7.00(d,1H,J＝2.1Hz),6.90(dd,1H,J
1＝8.2Hz J
2＝2.0Hz),6.78(d,1H,J＝8.2Hz),5.98(dd,1H,J
1＝15.8Hz J
2＝10.8Hz),5.6(m,1H),5.19(dd,1H,J
1＝15.8Hz J
2＝1.7Hz),5.02(dd,1H,J
1＝10.8Hz J
2＝1.7Hz),2.28(s,3H),2.23(m,4H),1.28(m,6H),1.22(m,3H).MS(ESI):302(C
19H
28NO
2,[M+H]
+).Anal.Calcd for C
19H
27NO
2:C,75.71；H,9.03；O,10.62Found:C,75.74；H,3.54；O,10.38
Embodiment 2:
2-(linalool)-N-(phenmethyl) ethanamide (compound 2)
Concrete steps are in the same manner as in Example 1, and difference is the para-totuidine in embodiment 1 step 3 to replace with meta-aminotoluene.
Gained compound is faint yellow.
1H NMR(DMSO,300MHz)δ:9.96(s,1H,NH),7.25(m,1H),6.98(d,1H,J＝2.1Hz),6.95(m,1H),6.90(dd,1H,J
1＝8.3Hz J
2＝2.1Hz),5.99(dd,1H,J
1＝15.8Hz J
2＝10.8Hz),5.4(m,1H),5.17(dd,1H,J
1＝15.8Hz J
2＝1.7Hz),5.07(dd,1H,J
1＝10.8Hz J
2＝1.7Hz),2.26(s,3H),2.22(m,4H),1.27(m,6H),1.22(m,3H).MS(ESI):302(C
19H
28NO
2,[M+H]+).Anal.Calcd for C
19H
27NO
2:C,75.71；H,9.03；O,10.62Found:C,75.73；H,3.55；O,10.37
Embodiment 3:
2-(linalool)-N-(to benzyloxy) ethanamide (compound 3)
Concrete steps are in the same manner as in Example 1, and difference is the para-totuidine in embodiment 1 step 3 to replace with methyl oxyaniline.
Gained compound is faint yellow.
1H NMR(DMSO,300MHz)δ:9.96(s,1H,NH),7.06(d,1H,J＝2.1Hz),6.96(d,1H,J＝8.2Hz),6.83(dd,1H,J
1＝8.5Hz J
2＝2.3Hz),6.72(d,1H,J＝8.5Hz),5.94(dd,1H,J
1＝15.8Hz J
2＝10.8Hz),5.53(m,1H),5.15(dd,1H,J
1＝15.8Hz J
2＝1.7Hz),5.04(dd,1H,J
1＝10.8Hz J
2＝1.7Hz),3.86(s,3H),2.23(m,4H),1.28(m,6H),1.22(m,3H).MS(ESI):318(C
19H
28NO
3,[M+H]+).Anal.Calcd for C
19H
27NO
3:C,71.89；H,8.57；O,15.12Found:C,71.81；H,8.55；O,15.12
Embodiment 4:
2-(linalool)-N-(benzyloxy) acetyl amination (compound 4)
Concrete steps are in the same manner as in Example 1, and difference is the para-totuidine in embodiment 1 step 3 to replace with meta-aminotoluene.
Gained compound is faint yellow.
1H NMR(DMSO,300MHz)δ:9.96(s,1H,NH),7.12(d,1H,J＝2.1Hz),6.88(dd,1H,J
1＝8.2Hz J
2＝2.1Hz),6.76(dd,1H,J
1＝8.4Hz),6.66(m,1H),5.91(dd,1H,J
1＝15.8Hz J
2＝10.8Hz),5.53(m,1H),5.18(dd,1H,J
1＝15.8Hz J
2＝1.7Hz),5.0(dd,1H,J
1＝10.8Hz J
2＝1.7Hz),3.92(s,3H),2.28(m,4H),1.28(m,6H),1.22(m,3H).MS(ESI):318(C
19H
28NO
3,[M+H]+).Anal.Calcd for C
19H
27NO
3:C,71.89；H,8.57；O,15.12Found:C,71.88；H,8.56；O,15.14
Embodiment 5:
2-(linalool)-N-(fluorine-based to benzene) ethanamide (compound 5)
Concrete steps are in the same manner as in Example 1, and difference is the para-totuidine in embodiment 1 step 3 to replace with para-fluoroaniline.
Gained compound is faint yellow.
1H NMR(DMSO,300MHz)δ:9.96(s,1H,NH),7.12(d,1H,J＝8.0Hz),6.98(d,1H,J＝2.0Hz),6.87(dd,1H,J
1＝8.2Hz J
2＝2.0Hz),6.77(d,1H,J＝8.2Hz),5.94(dd,1H,J
1＝15.8Hz J
2＝10.8Hz),5.56(m,1H),5.11(dd,1H,J
1＝15.8Hz J
2＝1.7Hz),5.06(dd,1H,J
1＝10.8Hz J
2＝1.7Hz),2.22(m,4H),1.28(m,6H),1.22(m,3H).MS(ESI):306(C
18H
25FNO
2,[M+H]+).Anal.Calcd for C
18H
24FNO
2:C,70.79；H,7.92；O,10.48Found:C,70.82；H,7.90；O,10.52
Embodiment 6:
2-(linalool)-N-(isophthalic is fluorine-based) ethanamide (compound 6)
Concrete steps are in the same manner as in Example 1, and difference is the para-totuidine in embodiment 1 step 3 to replace with m-fluoroaniline.
Gained compound is faint yellow.
1H NMR(DMSO,300MHz)δ:9.96(s,1H,NH),7.00(d,1H,J＝2.0Hz),6.94(m,1H),6.88(dd,1H,J
1＝8.2Hz J
2＝2.0Hz),6.79(d,1H,J＝8.2Hz),5.92(dd,1H,J
1＝15.8Hz J
2＝10.8Hz),5.57(m,1H),5.14(dd,1H,J
1＝15.8Hz J
2＝1.7Hz),5.09(dd,1H,J
1＝10.8Hz J
2＝1.7Hz),2.22(m,4H),1.28(m,6H),1.22(m,3H).MS(ESI):306(C
18H
25FNO
2,[M+H]+).Anal.Calcd for C
18H
24FNO
2:C,70.79；H,7.92；O,10.48Found:C,70.80；H,7.91；O,10.51
Embodiment 7:
The amide derivatives anti-microbial activity research of phantol
1. experiment material and method
1.1 medicines and reagent
Mueller-Hinton substratum (beef extract powder 5g, casein hydrolysate 17.5g, starch 1.5g, agar 12.5g, add in 1000mL distilled water), paraxin, penicillin, DMSO, MTT (3-(4,5-dimethylthiazole-2)-2,-diphenyltetrazolium bromide bromine salt, commodity are called tetrazolium bromide), Virahol, hydrochloric acid, be compound 1-6, PBS damping fluid (phosphate buffered saline buffer 0.01mol/L, pH7.4, the Na2HPO4.12H2O 2.9g of analytical reagent, synthesis, KH2PO40.2g, NaCl 8.0g, KCl0.2g, distillation 1000mL).
1.2 bacterial classification
Intestinal bacteria (E.coli), streptococcus aureus (S.aureus), bacillus subtilis (B.subtilis),
Pseudomonas aeruginosa (P.aeruginosa)
1.3 experimental technique
1.3.1 the preparation of substratum
Get beef extract powder 5g, casein hydrolysate 17.5g, starch 1.5g, agar 12.5g, add in 1000mL distilled water, heated and boiled is dissolved, packing, and 121 DEG C of autoclavings 15 minutes are for subsequent use.
1.3.2 the cultivation of test organisms
In sterilisable chamber, get intestinal bacteria, streptococcus aureus, subtilis and Pseudomonas aeruginosa four kinds of test strains, under spirit lamp with inoculating needle respectively on four kinds of test strain inclined-planes, scrape the inclined-plane lawn that takes a morsel, make bacteria suspension with a certain amount of sterilized water, then get a certain amount of being added to and melt and be cooled in the MH substratum of about 50 DEG C, shake up, at once pour in sterile petri dish, with after plug sealing after abundant condensation, cultivate 18-24h in 37 DEG C for subsequent use.Draw bacterium liquid 1mL, press 1:1000 dilution with MH substratum, make bacterial concentration be about 10
5cfu/mL.
1.3.3 antibacterial experiment:
Candidate drug is dissolved in DMSO the solution being mixed with 2mg/mL, then becomes finite concentration gradient (50 μ g/mL, 25 μ g/mL, 12.5pg/mL, 6.25 μ g/mL, 3.125 μ g/mL) with DMSO chemicals dilating with doubling dilution.In sterilizing microtiter plate Article 1, add the substratum of 100 μ L respectively, Article 2 is positive control, adds 100 μ L bacteria suspensions.The bacteria suspension of 90 μ L and the drug solution of 10 μ L is added in remaining hole.Parallel 3 times of each drug solution concentration.Bacteria name is indicated bottom microtiter plate.The culture dish processed is cultivated 24h in 37 DEG C, observes.
1.3.4MIC mensuration
After each microtiter plate can measure its MIC value intuitively, in each hole of plate, add 50 μ LPBS damping fluid (phosphate buffered saline buffer 0.01mol/L, pH 7.4, Na
2hPO
4.2H
2o 2.9g KH
2pO
40.2g, NaCl 8.0g, KCl 0.2g, distilled water 1000mL), wherein comprise 2mg MTT/mL.At room temperature continue to hatch 4-5h.Material in hole is shifted out and adds 100 μ L and contain the Virahol of 5%1mol/L HCl to extract dyestuff.Continue at room temperature to compose to educate 12h, measure each hole photoabsorption (OD value) in microplate reader, measure wavelength 550nm.Medicine is calculated to the minimum inhibition concentration of bacterial growth according to each hole OD value.
Minimum inhibition concentration (minimum inhibitory concentration, MIC): hatch 24 hours in certain circumstances, the lowest concentration of drug that certain microorganism can be suppressed to occur rising appreciably and minimum inhibition concentration, according to the optical density(OD) (OD value) measured, make the typical curve of bacterial growth inhibiting rate, typical curve is tried to achieve the drug level of its correspondence.The MIC recorded is shown in Table 1
2. experimental result
Table 1: the amide derivatives of institute of the present invention phantol is to the suppression MIC value (μ g/mL) of bacterium
Positive control: chloramphenicol; Penicillin
Result shows: the amide derivatives of phantol has suppression in various degree to intestinal bacteria (E.coli), streptococcus aureus (S.aureus), subtilis (B.subtilis), Pseudomonas aeruginosa (P.aeruginosa).
Claims (9)
1. an amide derivatives for phantol, is characterized in that having following structural formula:
Wherein, R is:
2. the preparation method of the amide derivatives of phantol as claimed in claim 1, is characterized in that comprising the following steps:
Step 1: join in anhydrous DMF solution by phantol and salt of wormwood, drips the DMF solution of methyl bromoacetate after stirring, add water, extraction into ethyl acetate after reaction terminates, and then dry, recrystallization, obtains linalool methyl acetate;
Step 2: linalool methyl acetate is added in the aqueous solution of NaOH, after reflux, be extracted with ethyl acetate, stay aqueous phase, aqueous phase drips rare HCl solution, till precipitation does not increase, obtain linalool acetic acid;
Step 3: by 3,7-dimethyl-1,6-octadiene-3-alcohol acetic acid, I-hydroxybenzotriazole and 1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate is dissolved in methylene dichloride, anils is joined in reaction soln, reaction mixture reflux is after 8 hours, decompression steams methylene dichloride, and crude product obtains target compound through alcohol crystal.
3. the preparation method of the amide derivatives of phantol as claimed in claim 2, it is characterized in that described step 1 is specially: join in anhydrous DMF solution by phantol and salt of wormwood, dropwise drip at 0 ~ 5 DEG C the DMF solution that concentration is 60% methyl bromoacetate after stirring, reaction soln adds water in 50 ~ 70 DEG C of reactions after 7 ~ 9 hours, extraction into ethyl acetate 3 times, dry crude product.Crude product obtains linalool methyl acetate through alcohol crystal.
4. the preparation method of the amide derivatives of phantol as claimed in claim 3, what it is characterized in that described phantol and salt of wormwood add-on mole is 1:1, described phantol and methyl bromoacetate add-on mole be 1:1.
5. the preparation method of the amide derivatives of phantol as claimed in claim 2, it is characterized in that described step 2 is specially: linalool methyl acetate being added concentration is in the aqueous solution of the NaOH of 10%, reflux 2 ~ 3h, then be extracted with ethyl acetate, stay aqueous phase, aqueous phase drips rare HCl solution, till precipitation does not increase, obtain linalool acetic acid.
6. the preparation method of the amide derivatives of phantol as claimed in claim 2, it is characterized in that described step 3 is specially: 3,7-dimethyl-1,6-octadiene-3-alcohol acetic acid, I-hydroxybenzotriazole and 1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate dissolve and are in methylene dichloride, anils is joined in reaction soln, reaction mixture reflux is after 7 ~ 9 hours, decompression steams methylene dichloride, and crude product obtains target compound through alcohol crystal.
7. the preparation method of the amide derivatives of phantol as claimed in claim 2, it is characterized in that 3,7-dimethyl-1,6-octadiene-3-alcohol acetic acid, the mol ratio of I-hydroxybenzotriazole and 1-ethyl-(3-dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate is 1:1:1.
8. the preparation method of the amide derivatives of phantol as claimed in claim 2, is characterized in that described anils is: para-totuidine, meta-aminotoluene, to methyl oxyaniline, a methyl oxyaniline, para-fluoroaniline or m-fluoroaniline.
9. the application of the amide derivatives of phantol as claimed in claim 1, is characterized in that using it in antibacterials.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114317105A (en) * | 2022-01-24 | 2022-04-12 | 四川幺麻子生物科技有限公司 | Volatile zanthoxylum oil, extraction method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562312A (en) * | 1966-11-04 | 1971-02-09 | Albert Eschenmoser | Manufacture of 2-substituted resorcinol derivatives |
| WO2005012210A2 (en) * | 2003-08-01 | 2005-02-10 | Dr. Andre Rieks - Labor Für Enzymtechnologie Gmbh | Antimicrobial active preparations containing terpene derivatives |
-
2015
- 2015-05-25 CN CN201510271836.XA patent/CN104892446B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3562312A (en) * | 1966-11-04 | 1971-02-09 | Albert Eschenmoser | Manufacture of 2-substituted resorcinol derivatives |
| WO2005012210A2 (en) * | 2003-08-01 | 2005-02-10 | Dr. Andre Rieks - Labor Für Enzymtechnologie Gmbh | Antimicrobial active preparations containing terpene derivatives |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114317105A (en) * | 2022-01-24 | 2022-04-12 | 四川幺麻子生物科技有限公司 | Volatile zanthoxylum oil, extraction method and application thereof |
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