CN108658846B - Quaternary ammonium salt containing cardanol group and application thereof - Google Patents

Quaternary ammonium salt containing cardanol group and application thereof Download PDF

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CN108658846B
CN108658846B CN201810600936.6A CN201810600936A CN108658846B CN 108658846 B CN108658846 B CN 108658846B CN 201810600936 A CN201810600936 A CN 201810600936A CN 108658846 B CN108658846 B CN 108658846B
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quaternary ammonium
ammonium salt
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王利民
黄蒙恩
车飞
张景清
马静怡
吴洵燊
田禾
赵敏
韩建伟
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Shanghai Bronkow Chemical Co ltd
East China University of Science and Technology
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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Abstract

The invention relates to a quaternary ammonium salt containing cardanol groups and application thereof. The quaternary ammonium salt is a compound shown in a formula I. The quaternary ammonium salt provided by the invention can be used as a cationic surfactant for resisting gram-positive bacteria.
Figure DDA0001693064040000011
In the formula I, R1Is a linear or branched alkyl group having carbon atoms greater than or equal to four, or a halogenated linear or branched alkyl group having carbon atoms greater than or equal to four; r2Is C15A chain hydrocarbon group of (1); x is halogen.

Description

Quaternary ammonium salt containing cardanol group and application thereof
Technical Field
The invention relates to a quaternary ammonium salt containing a cardanol group and application thereof, in particular to an asymmetric gemini quaternary ammonium salt containing a cardanol group and application thereof.
Background
Cardanol is a plant or grain-derived renewable raw material purified from Cashew Nut Shell Liquid (CNSL). Cardanol contains four different meta-alkylphenols. Because four monomer molecules of cardanol have various functional groups available for chemical derivatization: phenolic hydroxyl, benzene ring and carbon-carbon double bond on carbon long chain, cardanol is a molecular skeleton structure with derivation potential.
The group had used the meta position as C15The cardanol with chain alkyl is connected with an aromatic compound containing N through the chain alkyl with a certain length to obtain a cardanol derivative with a novel structure, and the cardanol derivative can be used as a cationic surfactant (CN 107892671A).
With the progress of the research, the inventors of the present invention found that: the asymmetric gemini quaternary ammonium salt based on bipyridyl and containing cardanol groups can be obtained through proper chemical modification. The obtained asymmetric gemini quaternary ammonium salt not only can be used as a cationic surfactant, but also has excellent antibacterial (particularly gram-positive bacterial strain) performance.
Disclosure of Invention
One object of the present invention is to provide a quaternary ammonium salt containing a cardanol group, which has a novel structure.
The quaternary ammonium salt is a compound shown in a formula I:
Figure BDA0001693064030000011
in the formula I, R1Is a straight chain or branched alkyl with carbon atom more than or equal to four, or a straight chain or branched alkyl with carbon atom more than or equal to four of halogen (F, Cl, Br or/and I, the same below); r2Is C15A chain hydrocarbon group of (1); x is halogen (F, Cl, Br or I, the same applies below).
It is another object of the present invention to disclose a use of the above quaternary ammonium salt. Namely the application of the compound shown in the formula I as a cationic surfactant for resisting gram-positive bacteria.
In addition, the invention also aims to provide a method for preparing the compound shown in the formula I. The method comprises the following steps:
(1) from 4, 4' -bipyridine
Figure BDA0001693064030000021
With alkyl halides (R)1X) reaction to prepare intermediate A
Figure BDA0001693064030000022
A step (2);
(2) prepared from cardanol
Figure BDA0001693064030000023
With halogenated hydrocarbons
Figure BDA0001693064030000024
Reaction to prepare intermediate B
Figure BDA0001693064030000025
A step (2); and the combination of (a) and (b),
(3) and (3) preparing a target product (the compound shown in the formula I) by reacting the intermediate A with the intermediate B.
The synthetic route is as follows:
Figure BDA0001693064030000026
wherein R is1,R2And X have the same meanings as described above.
Detailed Description
In a preferred embodiment of the present invention, R1Is C4～C14Straight or branched alkyl of (2), or halogenated C4～C14Linear or branched alkyl of (a);
the further preferred technical scheme is as follows: r1Is C4～C14Linear alkyl group of (1).
In another preferred embodiment of the present invention, R2Is C15Linear alkyl group of (1).
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are only for the understanding of the present invention, and are not intended to limit the scope of the present invention.
Example 1
Formula IAPreparation of the indicated compounds:
Figure BDA0001693064030000027
4, 4' -bipyridine (15mmol, 5equiv) and n-butyl bromide (3mmol, 1equiv) are dissolved in anhydrous acetonitrile, placed in a reaction treated with anhydrous water, reacted at 82 ℃ for 24 hours under the protection of argon, and the anhydrous acetonitrile is dried by spinning. Carrying out recrystallization by using methanol/ethyl acetate as a recrystallization solvent to obtain an intermediate A-A;
dissolving trans-1, 4-dibromo-2-butene (30mmol, 3equiv) in acetone, adding anhydrous potassium carbonate (60mmol, 6equiv), and stirring for 30 minutes; cardanol (10mmol, 1equiv) was also dissolved in acetone to give a clear solution. Slowly dropping the cardanol acetone solution into the acetone solution of the trans-1, 4-dibromo-2-butylene by using a constant-pressure dropping funnel. Stirred for 30 minutes. Heating the reaction system to 56 ℃, reacting for 24 hours, filtering, preparing a dry sample, and passing pure petroleum ether through a column to obtain an intermediate B-A;
dissolving intermediate A-A (1mmol, 1equiv) and intermediate B-A (1.2mmol, 1.2equiv) in anhydrous acetonitrile, placing in anhydrous treated reaction, reacting at 82 ℃ for 24 hours under the protection of argon, cooling to room temperature, performing suction filtration to obtain a solid, washing the solid (3X 15mL) with acetonitrile to obtain a beige solid (formula I)AThe compound shown).
1H NMR(400MHz,CD3OD):δ9.29-9.30(d,J＝4.0Hz,2H),9.25-9.27(d,J＝8.0Hz,2H),8.69-8.71(m,4H),7.14-7.18(m,1H),6.73-6.78(m,3H),6.23-6.44(m,2H),5.43-5.45(d,J＝8.0Hz,2H),4.74-4.78(t,J＝8.0Hz,2H),4.66-4.67(d,J＝4.0Hz,2H),2.54-2.58(t,J＝8.0Hz,2H),2.04-2.12(m,2H),1.55-1.62(m,2H),1.28-1.31(m,24H),1.02-1.06(t,J＝8.0Hz,3H),0.88-0.91(t,J＝6.0Hz,3H)；
13C NMR(101MHz,CD3OD):δ159.77,151.69,145.88,137.49,130.35,128.38,124.44,122.43,121.36,115.98,112.71,67.78,63.96,63.12,36.95,34.50,32.67,30.76,30.48,30.36,23.75,20.50,14.46,13.79.
HRMS(ESI-TOF)m/z:[M-2Br]2+Theoretical value (Calcd for) C39H58N2O285.2269; experimental value (Found)285.2271.
Example 2
Formula IBPreparation of the indicated compounds:
Figure BDA0001693064030000031
the procedure and conditions were the same as in example 1 except that n-butyl bromide in example 1 was replaced with n-hexane bromide to give the compound of formula IBThe compound shown (beige solid).
1H NMR(400MHz,CD3OD):δ9.28-9.30(d,J＝8.0Hz,2H),9.25-9.27(d,J＝8.0Hz,2H),8.69-8.70(m,4H),7.14-7.18(m,1H),6.73-6.78(m,3H),6.23-6.44(m,2H),5.43-5.44(d,J＝4.0Hz,2H),4.74-4.77(t,J＝6.0Hz,2H),4.66-4.67(d,J＝4.0Hz,2H),2.54-2.58(t,J＝8.0Hz,2H),2.06-2.13(m,2H),1.55-1.62(m,2H),1.28-1.47(m,30H),0.88-0.95(m,6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.69,145.88,137.49,130.35,128.37,124.44,122.43,121.20,115.98,112.70,67.77,63.97,63.34,36.95,33.09,32.66,32.56,30.76,30.48,30.36,26.93,23.75,23.52,14.45,14.28.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C41H62N2O 299.2426；Found 299.2419。
Example 3
Formula ICPreparation of the indicated compounds:
Figure BDA0001693064030000041
the procedure and conditions were the same as in example 1 except that n-octane bromide was used instead of n-butyl bromide in example 1 to give the compound of formula ICThe compound shown (beige solid).
1H NMR(400MHz,CD3OD):δ9.29-9.30(d,J＝4.0Hz,2H),9.25-9.27(d,J＝8.0Hz,2H),8.69-8.71(m,4H),7.14-7.18(m,1H),6.73-6.78(m,3H),6.23-6.44(m,2H),5.43-5.45(d,J＝8.0Hz,2H),4.74-4.77(t,J＝6.0Hz,2H),4.66-4.67(d,J＝4.0Hz,2H),2.54-2.57(t,J＝6.0Hz,2H),2.06-2.13(m,2H),1.55-1.62(m,2H),1.28-1.44(m,34H),0.88-0.92(m,6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.69,145.88,137.49,130.35,128.38,124.45,122.43,121.63,115.99,112.71,67.78,63.96,63.36,36.95,33.09,32.90,32.66,32.61,30.76,30.48,30.36,30.14,27.26,23.75,23.68,14.46,14.41.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C43H66N2O 313.2582；Found 313.2589.
Example 4
Formula IDPreparation of the indicated compounds:
Figure BDA0001693064030000051
the procedure and conditions were the same as in example 1 except that n-decane bromide was used instead of n-butane bromide in example 1, to obtain the compound of formula ICThe compound shown (beige solid).
1H NMR(400MHz,CD3OD):δ9.29-9.30(d,J＝4.0Hz,2H),9.25-9.27(d,J＝8.0Hz,2H),8.69-8.71(m,4H),7.14-7.18(m,1H),6.73-6.77(m,3H),6.23-6.45(m,2H),5.43-5.45(d,J＝8.0Hz,2H),4.74-4.77(t,J＝6.0Hz,2H),4.66-4.67(d,J＝4.0Hz,2H),2.54-2.57(t,J＝6.0Hz,2H),2.06-2.13(m,2H),1.53-1.61(m,2H),1.27-1.44(m,38H),0.87-0.91(t,J＝8.0Hz,6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.27,145.87,137.49,130.35,128.39,124.46,122.42,121.42,116.00,112.71,67.79,63.95,63.37,36.96,33.09,33.05,32.67,32.61,30.77,30.62,30.55,30.42,30.18,27.27,23.71,14.44.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C45H70N2O 327.2738；Found 327.2732.
Example 5
Formula IEPreparation of the indicated compounds:
Figure BDA0001693064030000052
the procedure and conditions were the same as in example 1 except that n-butyl bromide in example 1 was replaced with dodecane bromide to give the compound of formula IEThe compound shown (beige solid).
1H NMR(400MHz,CD3OD):δ9.28-9.30(d,J＝8.0Hz,2H),9.25-9.27(d,J＝8.0Hz,2H),8.68-8.71(m,4H),7.14-7.18(m,1H),6.73-6.78(m,3H),6.24-6.43(m,2H),5.43-5.45(d,J＝8.0Hz,2H),4.73-4.77(t,J＝8.0Hz,2H),4.66-4.67(d,J＝4.0Hz,2H),2.54-2.57(t,J＝6.0Hz,2H),2.06-2.13(m,2H),1.55-1.62(m,2H),1.28-1.44(m,42H),0.87-0.91(t,J＝8.0Hz,6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.29,145.88,137.49,130.35,129.85,124.45,122.43,115.96,112.70,67.78,63.96,63.37,36.95,33.08,32.67,32.61,30.76,30.48,30.36,30.18,27.27,23.75,14.45.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C47H74N2O 341.2895；Found 341.2908.
Example 6
Formula IFPreparation of the indicated compounds:
Figure BDA0001693064030000061
except that bromotetradecane is substituted for bromine in example 1The procedure and conditions other than n-butane substitution were the same as in example 1 to obtain the compound of formula IFThe compound shown (beige solid).
1H NMR(400MHz,CD3OD):δ9.28-9.30(d,J＝8.0Hz,2H),9.25-9.27(d,J＝8.0Hz,2H),8.69-8.71(m,4H),7.14-7.18(m,1H),6.73-6.77(m,3H),6.23-6.44(m,2H),5.43-5.45(d,J＝8.0Hz,2H),4.74-4.77(t,J＝6.0Hz,2H),4.66-4.67(d,J＝4.0Hz,2H),2.53-2.57(t,J＝8.0Hz,2H),2.06-2.13(m,2H),1.55-1.62(m,2H),1.28-1.44(m,46H),0.87-0.91(t,J＝8.0Hz,6H)；
13C NMR(101MHz,CD3OD):δ159.77,151.27,145.87,137.48,130.35,128.39,124.46,122.42,121.42,116.00,112.70,67.78,63.95,63.36,36.96,33.09,32.68,32.62,30.78,30.37,30.19,27.27,23.76,14.46.
HRMS(ESI-TOF)m/z:[M-2Br]2+Calcd for C49H78N2O 355.3052；Found 355.3042.
Example 7
Formula IGPreparation of the indicated compounds:
Figure BDA0001693064030000071
the procedure and conditions were the same as in example 1 except that perfluorobutylethyl iodide was used instead of n-butyl bromide in example 1 to give formula IGThe compound shown (beige solid).
1H NMR(400MHz,CD3OD):δ9.42-9.43(d,J＝4.0Hz,2H),9.26-9.28(d,J＝8.0Hz,2H),8.75-8.77(d,J＝8.0Hz,2H),7.14-7.18(m,1H),6.73-6.78(m,3H),6.24-6.45(m,2H),5.43-5.45(d,J＝8.0Hz,2H),4.66-4.67(d,J＝4.0Hz,2H),3.18-3.27(m,2H),2.54-2.58(t,J＝8.0Hz,2H),1.55-1.62(m,2H),1.28-1.31(m,24H),0.88-0.91(t,J＝4.0Hz,3H)；
13C NMR(101MHz,CD3OD):δ159.76,151.40,145.58,142.64,130.35,128.59,126.55,124.39,122.43,120.68,118.70,118.63,115.98,112.69,111.53,67.76,64.01,62.83,36.96,33.09,32.68,30.77,30.49,30.37,24.55,23.76,14.46.
HRMS(ESI-TOF)m/z:[M-I-Br]2+Calcd for C41H53F9N2O 380.2002；Found 380.1995.
Example 8
Compound IA-IGTesting of surface Properties
Due to the compound IA-IGThere are differences in solubility properties of (A) which we divided into two groups. Group I (Compound I)AAnd IB) Group II (Compound I)C-IG) The surface properties were measured separately.
Group I (Compound I)AAnd IB) The specific test method is as follows:
respectively preparing a compound I with the concentration of 0.001mol/LAAnd IBThe mother liquor of (4). First, the surface tension of 10mL of deionized water was measured. Then, a pipette was used to sequentially drop a specific volume of the test compound (Compound I)AAnd IB) The surface tension of the solution is measured after the mother solution is uniformly stirred, three groups of experimental data are recorded, and an average value is obtained. The above steps are repeated until the surface tension of the solution becomes stable.
According to a series of data of the measured surface tension changing with the concentration, the compound I is obtained by calculationAAnd IBThe surface property parameter of (1). Including Critical Micelle Concentration (CMC), surface tension (γ) of the aqueous solution at CMCCMC) Surface pressure (pi)CMC) Adsorption efficiency (C)20) Saturation adsorption (. tau.) at interfaceCMC) And molecular area of surfactant at saturation adsorption at gas-water interface (A)min). See in particular table 1 (compound I)AAnd IBSurface property parameter(s).
Second group (Compound I)C-IG) The specific test method is as follows:
respectively preparing a compound I with the concentration of 1mmol/LC-IGAnd the surface tension at that concentration is determined and used to characterize its ability to reduce the surface tension of an aqueous solution. See in particular table 2 (compound I)C-IGSurface property parameter(s).
Table 1.
Figure BDA0001693064030000081
Table 2.
Figure BDA0001693064030000082
Table 1. CTAB is a currently commercially available cationic surfactant: cetyl trimethylammonium bromide (as control).
As can be seen from tables 1 and 2, Compound IA-IGCan be used as cationic surfactant, and part of the compound (compound I)AAnd IB) The surface properties of (a) are far superior to those of CTAB.
Example 9
Compound IA-IGTesting of antibacterial Activity
The test strains were gram-positive strains staphylococcus aureus (s. aureus atcc 25923) and corynebacterium glutamicum (c. glutamicumacc 13032).
The specific test method is as follows:
draw 100. mu.L of cryopreserved glycerol vial solution and inoculate into shake flasks containing 50mL of brain-heart leachate broth. The culture was carried out overnight at 220rpm at 30 ℃. The test compound (Compound I)A-IG) Dissolving with 1mL of methanol, and diffusing into 9mL of sterile water to prepare a compound mother solution to be detected with the concentration of 1280 mu g/mL. A solvent control containing no compound and only 1mL methanol and 9mL sterile water, a blank control containing only 10mL sterile water, and a commercial antimicrobial: cetyl trimethylammonium chloride (Benzalkoniumchloride, abbreviated as "BAC") was used as a positive control.
1mL of the test compound mother solution was aspirated, the resulting solution was filtered through a 0.22 μm organic phase filter, and the resulting solution was collected in a 2mL cuvette, and 11 concentrations of test compound were obtained by two-fold dilution (the concentrations were 1280 μ g/mL, 640 μ g/mL, 320 μ g/mL, 160 μ g/mL, 80 μ g/mL, 40 μ g/mL, 20 μ g/mL, 10 μ g/mL, 5 μ g/mL, 2.5 μ g/mL, and 1.25 μ g/mL in this order). 10. mu.L of each of 11 test solutions of different concentrations of compound were taken and added to the designated wells of a 96-well plate. Meanwhile, overnight-cultured bacteria liquid is taken out, 2mL to 200mL of liquid culture medium is sucked from the overnight-cultured bacteria liquid, and 90 mu L of bacteria liquid is sucked into a 96-well plate after uniform shaking. The concentration of the test compound at this time was 128. mu.g/mL, 64. mu.g/mL, 32. mu.g/mL, 16. mu.g/mL, 8. mu.g/mL, 4. mu.g/mL, 2. mu.g/mL, 1. mu.g/mL, 0.5. mu.g/mL, 0.25. mu.g/mL and 0.125. mu.g/mL.
The plate with the added bacterial solution and test compound solution was placed in a shaker and incubated at a suitable temperature for 24 hours at a rotation speed of 220 rpm. After the culture was completed, the growth of the bacteria was visually observed (turbidity means good growth of the bacteria, and clarity means inhibition of the growth of the bacteria). The Minimum Inhibitory Concentration (MIC) is defined as the lowest Concentration of a compound that can inhibit the growth of bacteria in the microwells. The experimental results show that the solvent methanol can not inhibit the growth of bacteria, so that the antibacterial test is not interfered.
Compound IA-IGThe MIC values are shown in Table 3.
Table 3.
Figure BDA0001693064030000091
From Table 3, it can be seen that Compound IA-IGThe majority of compounds have antibacterial activity against gram-positive bacteria, and part of the compounds (compound I)EAnd IF) The antibacterial property of (a) is close to that of a commercially available antibacterial agent (BAC).

Claims (5)

1. A quaternary ammonium salt containing cardanol group is a compound shown in formula I:
Figure FDA0002928874240000011
in the formula I, R1Is C4～C14Of a straight chain orBranched alkyl radical, R2Is C15A chain alkyl group of (4); x is halogen.
2. The quaternary ammonium salt of claim 1, wherein R is2Is C15Linear alkyl group of (1).
3. The quaternary ammonium salt of claim 1 or 2, wherein the quaternary ammonium salt is of formula IEOr IFA compound shown in the specification:
Figure FDA0002928874240000012
4. use of a quaternary ammonium salt according to claim 1 or 2 as a cationic surfactant against gram-positive bacteria;
wherein the gram-positive bacterium is staphylococcus aureus (s.aureus ATCC 25923) or corynebacterium glutamicum (c.glutamicum ATCC 13032).
5. Use of a quaternary ammonium salt according to claim 3 as a cationic surfactant against gram-positive bacteria;
wherein the gram-positive bacterium is staphylococcus aureus (s.aureus ATCC 25923) or corynebacterium glutamicum (c.glutamicum ATCC 13032).
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