Amide derivatives of linalool, preparation method of amide derivatives and application of amide derivatives in bacteria prevention

A technology of linalool and amides, which is applied in the preparation of carboxylic acid amides, antibacterial drugs, organic compounds, etc., and can solve the problems of not reaching treatment and accelerating the speed of drug resistance, etc.

Active Publication Date: 2015-09-09
JIANGSU NAIQUE BIOLOGICAL ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The mutation of bacteria leads to their resistance to antibiotics, and the abuse of antibiotics accelerates the speed of drug resistance, which makes bacteria have strong drug resistance, so that the original antibacterial drugs can no longer reach the therapeutic effect. effect, so the development of antibacterial drugs with new structures is imminent

Method used

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  • Amide derivatives of linalool, preparation method of amide derivatives and application of amide derivatives in bacteria prevention
  • Amide derivatives of linalool, preparation method of amide derivatives and application of amide derivatives in bacteria prevention
  • Amide derivatives of linalool, preparation method of amide derivatives and application of amide derivatives in bacteria prevention

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 2-(3,7-Dimethyl-1,6-octadien-3-ol)-N-(p-phenylmethyl)acetamide (compound 1)

[0025]

[0026] Step 1: 30.1 g of linalool and 13.8 g of potassium carbonate were added to 100 mL of anhydrous DMF solution, and after stirring, 15.2 g of methyl bromoacetate in 10 mL of DMF solution was added dropwise at 0°C. The reaction solution was reacted at 60° C. for 8 hours, then added with 300 mL of water, extracted three times with ethyl acetate, and dried to obtain a crude product. The crude product was crystallized from ethanol to obtain methyl 3,7-dimethyl-1,6-octadien-3-ol acetate.

[0027] Step 2: Add 20 g of methyl 3,7-dimethyl-1,6-octadien-3-ol acetate into 100 mL of 10% NaOH aqueous solution, heat to reflux for 2 h, extract with ethyl acetate, and keep the water phase. Dilute HCl solution was added dropwise to the aqueous phase until the precipitation did not increase to obtain 3,7-dimethyl-1,6-octadien-3-ol acetic acid.

[0028] Step 3: 21.2 g of compound C, 13.5 g of H...

Embodiment 2

[0031] 2-(3,7-Dimethyl-1,6-octadien-3-ol)-N-(m-benzyl)acetamide (compound 2)

[0032]

[0033] The specific steps are the same as in Example 1, except that p-toluidine in Step 3 of Example 1 is replaced by m-toluidine.

[0034] The obtained compound was pale yellow. 1 H 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 19 h 28 NO 2 ,[M+H]+).Anal.Calcd for C 19 h 27 NO 2 :C,75.71;H,9.03;O,10.62Found:C,75.73;H,3.55;O,10.37

Embodiment 3

[0036] 2-(3,7-Dimethyl-1,6-octadien-3-ol)-N-(p-phenylmethoxy)acetamide (Compound 3)

[0037]

[0038] The specific steps are the same as in Example 1, except that the p-toluidine in step 3 of Example 1 is replaced by p-methoxyaniline.

[0039] The obtained compound was pale 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 19 h 28 NO 3 ,[M+H]+).Anal.Calcd for C 19 h 27 NO 3 :C,71.89;H,8.57;O,15.12Found:C,71.81;H,8.55;O,15.12

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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 [0001] The invention belongs to the field of organic synthesis, and in particular relates to an amide derivative of linalool, its preparation method and its application in antibacterial activity. Background technique [0002] Linalool is an enol substance of chain-like oxygen-containing monoterpene derivatives. The scientific name is 3,7-dimethyl-1,6-octadien-3-ol. alcohol, coriander alcohol, coriander alcohol, etc. Linalool exists not only in camphor, but also in plants such as coriander, lavender, jasmine, and saffron. Linalool has good antibacterial activity. Studies have shown that linalool has good inhibitory effects on Escherichia coli, Salmonella typhimurium, Listeria, and Vibrio vulnificus. Experiments have shown that the antibacterial activity of linalool is 5 times that of phenol. [0003] Antibiotic resistance has long been a major concern in global healthcare. The mutation of bacteria leads to their resistance to antibiotics, and the abuse of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C235/16A61P31/04
Inventor 杨永安袁继文钟慧易铭金显友魏元刚
Owner JIANGSU NAIQUE BIOLOGICAL ENG
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