Antibacterial compounds

Abstract

Provided are novel compounds, more particularly, novel compounds exhibiting excellent antibacterial properties while having a polymerizable functional group to prepare antibacterial polymers.

Description

Technical Field

[0001] Cross-reference to related applications

[0002] This application is based on and claims priority to Korean Patent Application Nos. 10-2021-0093703 and 10-2022-0078380, filed on July 16, 2021 and June 27, 2022, respectively, the disclosure of which is incorporated herein by reference in its entirety.

[0003] This invention relates to novel compounds that exhibit antibacterial properties. Background Technology

[0004] Recently, with the diversification of lifestyles, the improvement of living standards, and changes and increases in awareness, there has been a growing interest in improving the hygiene and comfort of one's personal living environment. Consequently, research has been conducted on microorganisms that threaten these environments. However, many types of microorganisms exist in everyday life and are widely distributed in nature, causing serious problems.

[0005] In particular, microorganisms such as bacteria and fungi can inhabit various environments, including food, living spaces, clothing, and industrial products. However, bacteria can cause various inflammations or food poisoning, and fungi can not only produce odors but also cause various skin diseases, respiratory illnesses, allergic reactions, atopic dermatitis, and other problems, making them problematic. Furthermore, microorganisms living on the surfaces of electronic products and household items can lead to product performance degradation.

[0006] Therefore, in order to prevent these microorganisms from causing harm to humans, various antimicrobial substances have been developed to inhibit the growth of microorganisms or kill them.

[0007] Specifically, previously developed antimicrobial agents can be broadly categorized into inorganic and organic antimicrobial agents. Inorganic antimicrobial agents contain metals such as silver and copper, and due to their excellent thermal stability, they retain their antimicrobial properties even at high temperatures. However, they are expensive and may discolor after processing due to the presence of metal ions. Organic antimicrobial agents, on the other hand, are cheaper than inorganic ones and exhibit excellent antimicrobial effects even in small quantities. However, organic antimicrobial agents suffer from poor antimicrobial durability due to the possibility of leaching after application to products.

[0008] In addition, although organic antimicrobial agents can ensure product stability in terms of inhibiting microbial growth and killing microorganisms, they are toxic and can irritate the user's skin.

[0009] For this reason, the introduction of antimicrobial substances in polymeric form into articles has been discussed to prevent the reduction of antimicrobial properties and safety issues due to the leaching of antimicrobial substances. Therefore, there is a need for antimicrobial monomers with polymerizable functional groups to synthesize antimicrobial polymers while retaining the excellent antimicrobial properties of the compounds themselves.

[0010] [Existing Technical Documents]

[0011] [Patent Literature]

[0012] (Patent Document 0001) Korean Patent No. 10-0601393 Summary of the Invention

[0013] Technical issues

[0014] This provides a new compound with excellent bacterial growth inhibitory activity.

[0015] An antimicrobial agent containing the compound is also provided.

[0016] Technical solution

[0017] In order to achieve the above objectives,

[0018] Compounds represented by the following chemical formula 1 are provided:

[0019] [Chemical Formula 1]

[0020]

[0021] In chemical formula 1,

[0022] Y is O, S, or N (R7),

[0023] L is a single bond, an alkylene group having 1 to 10 carbon atoms, or an aryl group having 6 to 60 carbon atoms.

[0024] R1 to R3 are each independently hydrogen or methyl.

[0025] R4 to R7 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0026] X - It is a conjugate base of an aromatic acid having 6 to 20 carbon atoms, wherein the conjugate base of the aromatic acid is substituted with one or more hydroxyl groups.

[0027] The conjugate base of the aromatic acid may be further substituted with one or more substituents selected from halogens, alkyl groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms.

[0028] It also provides antimicrobial agents containing compounds represented by chemical formula 1.

[0029] Beneficial effects

[0030] The compounds according to the invention are beneficial because they have excellent bacterial growth inhibition effects and contain polymerizable functional groups to prepare polymers exhibiting antibacterial properties. Attached Figure Description

[0031] Figure 1 The MS spectrum of compound A is shown;

[0032] Figure 2 Compound A is shown. 1 H NMR spectrum;

[0033] Figure 3 Compound 1 is shown. 1 H NMR spectrum; and

[0034] Figure 4 The mass spectrum of compound 1 is shown. Detailed Implementation

[0035] In this invention, the terms "first", "second", etc. are used to describe multiple components, and these terms are used only to distinguish one component from another.

[0036] Furthermore, the terminology used in this specification is for illustrative purposes only and is not intended to limit the invention. Singular expressions may include plural expressions unless the context otherwise allows. It must be understood that the terms “comprising,” “equipped,” or “having” in this specification are used only to specify the presence of an effective characteristic, number, step, component, or combination thereof, and do not preclude the presence or possibility of adding one or more different characteristics, numbers, steps, components, or combinations thereof.

[0037] Furthermore, in this invention, when referring to layers or elements being formed "on" or "above" a layer or element, it means that each layer or element is formed directly on the layer or element, or that other layers or elements may be formed between layers, objects, or substrates.

[0038] This invention can be modified and has various forms, and specific exemplary embodiments are illustrated and described in detail in the following description. However, it is not intended to limit the invention to the specific exemplary embodiments, and it must be understood that the invention includes every modification, equivalent, or alternative included within the spirit and scope of the invention.

[0039] Furthermore, the terminology used in this specification is for illustrative purposes only and is not intended to limit the invention. Unless the context otherwise allows, the singular expressions used herein may include the plural expressions.

[0040] At the same time, as used herein, the term "(meth)acrylate" includes both acrylate and methacrylate.

[0041] Furthermore, in this specification, the alkyl group can be straight-chain or branched, and its number of carbon atoms is not particularly limited, but is preferably 1 to 20. According to one embodiment, the alkyl group has 1 to 16 carbon atoms. According to one embodiment, the alkyl group has 1 to 12 carbon atoms. According to one embodiment, the alkyl group has 8 to 12 carbon atoms. Specific examples of alkyl groups may include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1,-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, etc. Furthermore, the above description of alkyl groups in this specification can also be applied to alkylene groups, except that alkylene groups are divalent groups.

[0042] Furthermore, in this specification, the aryl group is not particularly limited, but it is preferably composed of 6 to 60 carbon atoms, and can be monocyclic or polycyclic aryl. According to one embodiment, the aryl group has 6 to 20 carbon atoms. According to another embodiment, the aryl group has 6 to 10 carbon atoms. Monocyclic aryl groups may include, but are not limited to, phenyl, biphenyl, terphenyl, etc. Polycyclic aryl groups may include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. Aryl, fluorene, etc., but not limited to these. Furthermore, the above description of aryl in this specification can also be applied to arylene groups, the difference being that arylene groups are divalent groups.

[0043] Furthermore, in this specification, the term "substituted or unsubstituted" can be understood as "unsubstituted or substituted with one or more (e.g., one to five) substituents selected from deuterium, halogen, cyano, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms".

[0044] Furthermore, in this specification, alkoxy is a substituent in which an oxygen atom is bonded to the linking portion of an alkyl group to another atom, and the above description of alkyl can also be applied to the alkyl group.

[0045] To impart antimicrobial properties to household chemical products commonly used in everyday living spaces such as homes, offices, and multi-purpose facilities, an antimicrobial coating is applied to the surface of these products to prevent and / or kill the growth of microorganisms such as bacteria. In this process, the antimicrobial agent contained in the coating disrupts the cell membrane or cell wall of the microorganisms or causes denaturation of their proteins, thereby inhibiting microbial growth and preventing or killing the microorganisms.

[0046] Furthermore, over 5,000 species of bacteria have been identified. Specifically, bacteria exhibit diverse cell morphologies, such as spherical, rod-shaped, and spiral, and their oxygen requirements also differ, thus they are classified as aerobic, facultative, and anaerobic bacteria. Therefore, it is generally not easy for a single type of antibacterial agent to possess a physical / chemical mechanism that disrupts the cell membrane / cell wall or denatures the proteins of various bacteria.

[0047] Furthermore, there is the issue of antimicrobial agents used in products leaching out over time, and concerns that users' health may be threatened by the leached antimicrobial substances when exposed to them. Therefore, the introduction of antimicrobial agents in the form of polymers rather than single compounds has been discussed to prevent the degradation of antimicrobial properties and safety issues caused by the leaching of antimicrobial substances.

[0048] Therefore, the inventors have discovered that when a compound has a structure in which a salt compound containing a quaternary ammonium cation having a polymerizable functional group and an anion having a specific structure is combined, the compound itself can exhibit antibacterial properties against at least one of Gram-positive and Gram-negative bacteria, more specifically, all Gram-positive and Gram-negative bacteria, while the polymerizable functional group introduced into the molecule enables the synthesis of antibacterial polymers such as homopolymers or copolymers, thus completing the present invention.

[0049] Specifically, the anion contained in the compound is not a halide anion, but a conjugate base of an aromatic acid having 6 to 20 carbon atoms, wherein the conjugate base of the aromatic acid is substituted with one or more hydroxyl groups (-OH). More specifically, the anion has an aromatic ring structure, wherein one or more hydroxyl groups (-OH) and one or more carboxylate groups (-COO-) are substituted. With such a structure, the hydroxyl groups (-OH) contained in the molecule interact with the surface of bacterial cells to break down the cell membrane and cause the contents to coagulate, thereby further improving the antibacterial properties of the compound. In addition, due to the carboxylate groups (COO-) contained in the molecule, stable salts can be formed.

[0050] Furthermore, as used herein, “exhibiting antimicrobial properties against specific bacteria” means that a compound (antimicrobial substance) to be tested for antimicrobial properties is added to the culture medium of the test bacteria, and after culturing, the number of bacteria is significantly reduced compared to a reference without the antimicrobial substance. Specifically, this means that the antimicrobial rate (%) calculated by Equation 1 below, based on the assessment of antimicrobial properties described later, is 70% or greater.

[0051] [Equation 1]

[0052]

[0053] In this equation,

[0054] A s (A 样品 The absorbance of the culture medium containing antibacterial substances at a wavelength of 600 nm represents the absorbance of the medium.

[0055] A0(A 参照 () represents the absorbance of pure culture medium without antibacterial substances at a wavelength of 600 nm.

[0056] More preferably, "exhibiting antibacterial properties against specific bacteria" means that the antibacterial rate (%) calculated according to Equation 1 is 70% or greater, 70.6% or greater, 75.5% or greater, 80% or greater, 90% or greater, 95% or greater, 95.3% or greater, 95.8% or greater, 96% or greater, 97% or greater, 97.3% or greater, 98% or greater, 98.1% or greater, and 100% or less.

[0057] Furthermore, Gram-positive bacteria refer to bacteria that stain purple when stained using the Gram staining method. The cell walls of Gram-positive bacteria are composed of several layers of peptidoglycan. After staining with a basic dye such as crystal violet, Gram-positive bacteria do not lose their color even when treated with ethanol, and retain their purple hue. Bacteria classified as Gram-positive include *Enterococcus faecalis*, *Staphylococcus aureus*, *Streptococcus pneumoniae*, *Enterococcus faecium*, and *Lactobacillus lactis*, among others.

[0058] Furthermore, Gram-negative bacteria refer to bacteria that stain red using the Gram staining method and, compared to Gram-positive bacteria, possess an outer membrane composed of lipopolysaccharides, lipoproteins, and other complex polymeric substances rather than a cell wall with a relatively small amount of peptidoglycan. Therefore, after staining with a basic dye such as crystal violet, Gram-negative bacteria decolorize even when treated with ethanol, and appear red when counterstained with a red dye such as safranin. Bacteria classified as Gram-negative include *Proteus mirabilis*, *Escherichia coli*, *Salmonella typhi*, *Pseudomonas aeruginosa*, and *Vibrio cholerae*, among others.

[0059] Therefore, since Gram-positive and Gram-negative bacteria can cause various diseases upon contact and may also cause secondary infections in critically ill patients with weakened immune systems, it is preferable to use a single antibacterial agent that exhibits antibacterial properties against both Gram-positive and Gram-negative bacteria.

[0060] Furthermore, the compound according to one embodiment exhibits antibacterial properties against at least one of Gram-positive and Gram-negative bacteria due to the cations and anions of the quaternary ammonium salt. Specifically, the ammonium cation of the quaternary ammonium salt is electrostatically adsorbed onto the cell wall of either Gram-positive or Gram-negative bacteria, and then interacts with the hydrophobic alkyl group of the quaternary ammonium salt. As a result, the bacterial cell surface structure is disrupted, thereby inhibiting bacterial growth. In addition, the hydroxyl group (-OH) of the quaternary ammonium salt anion interacts with the surface of the bacterial cell to break down the cell membrane and cause coagulation of the contents, thereby further inhibiting bacterial growth.

[0061] The compounds and antimicrobial agents comprising them will be described in more detail below according to specific embodiments of the present invention.

[0062] compound

[0063] One embodiment of the compound is represented by the following chemical formula 1:

[0064] [Chemical Formula 1]

[0065]

[0066] In chemical formula 1,

[0067] Y is O, S, or N (R7),

[0068] L is a single bond, an alkylene group having 1 to 10 carbon atoms, or an aryl group having 6 to 60 carbon atoms.

[0069] R1 to R3 are each independently hydrogen or methyl.

[0070] R4 to R7 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0071] X - It is a conjugate base of an aromatic acid having 6 to 20 carbon atoms, wherein the conjugate base of the aromatic acid is substituted with one or more hydroxyl groups.

[0072] In addition to one or more hydroxyl groups, the conjugate base of the aromatic acid may be unsubstituted or substituted with one or more substituents selected from halogens, alkyl groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms.

[0073] Here, the conjugate base of the aromatic acid may be further substituted with one or more substituents selected from halogens, alkyl groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms.

[0074] In other words, apart from one or more hydroxyl groups, the conjugate base of an aromatic acid may be unsubstituted or substituted with one or more substituents (e.g., 1 to 5 substituents) selected from halogens, alkyl groups having 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms.

[0075] In chemical formula 1, Y can be O, S, or NH. Preferably, Y can be O.

[0076] In chemical formula 1, L can be methylene, ethylene, or propylene.

[0077] In addition, R1 can be hydrogen or methyl, and R2 and R3 can be hydrogen.

[0078] Furthermore, one of the three terminal groups (R4, R5, and R6 substituents) substituted in the quaternary ammonium cation of the first repeating unit can be an alkyl group having 5 to 20 carbon atoms. More specifically, one of R4 to R6 can be a linear (i.e., straight-chain) alkyl group having 5 to 20 carbon atoms. In this regard, the problem is that when all of the R4, R5, and R6 substituents are alkyl groups having fewer than 5 carbon atoms, the antibacterial properties may not be exhibited, and when any of the R4, R5, and R6 substituents is an alkyl group having more than 20 carbon atoms, the starting material used to prepare the copolymer is insoluble in the solvent, and therefore the synthesis itself is impossible.

[0079] More specifically, one of R4 to R6 can be an alkyl group having 5 to 20 carbon atoms, and the others can each be an alkyl group having 1 to 4 carbon atoms.

[0080] For example, one of R4 to R6 may be an alkyl group having 5 to 20 carbon atoms, and the others may each be methyl or ethyl. Preferably, R5 may be an alkyl group having 5 to 20 carbon atoms, and R4 and R6 may each be methyl or ethyl.

[0081] More specifically, R1 can be methyl, R2 and R3 can be hydrogen, one of R4 to R6 can be an alkyl group having 5 to 20 carbon atoms, and the remainder can each be methyl or ethyl independently; or

[0082] All of R1 to R3 can be hydrogen, one of R4 to R6 can be an alkyl group having 5 to 20 carbon atoms, and the remainder can each be methyl or ethyl independently.

[0083] Furthermore, for example, one of R4 to R6 can be an alkyl group having 6 to 16 carbon atoms, and the others can each be methyl or ethyl. Preferably, R5 can be an alkyl group having 6 to 16 carbon atoms, and R4 and R6 can each be methyl or ethyl.

[0084] Furthermore, for example, one of R4 to R6 can be an alkyl group having 8 to 12 carbon atoms, and the others can each be methyl or ethyl independently. Preferably, R5 can be an alkyl group having 8 to 12 carbon atoms, and R4 and R6 can each be methyl or ethyl independently.

[0085] Furthermore, in the R4, R5, and R6 substituents, the two substituents other than the alkyl group having 5 to 20 carbon atoms can be identical to each other.

[0086] Preferably, in Formula 1, one of R4, R5 and R6 may have 6 or more, 7 or more, or 8 or more carbon atoms, and 20 or fewer, 18 or fewer, 16 or fewer, 14 or fewer, or 12 or fewer carbon atoms.

[0087] For example, R1 can be methyl, R2 and R3 can be hydrogen, R4 can be an alkyl group having 6 to 16 carbon atoms, and R5 and R6 can each be methyl or ethyl independently. Antimicrobial copolymers comprising the first repeating unit of the structure described above can exhibit excellent antimicrobial properties against at least one of Gram-positive and Gram-negative bacteria, more specifically against all Gram-positive and Gram-negative bacteria.

[0088] Furthermore, R7 can be hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 20 carbon atoms. For example, R7 can be hydrogen, methyl, or phenyl.

[0089] Meanwhile, in Formula 1, the compound comprises an aromatic acid having 6 to 20 carbon atoms substituted with one or more hydroxyl groups (-OH), more specifically, a conjugate base of an aromatic acid having 6 to 20 carbon atoms substituted with 1 to 3 hydroxyl groups, as a counterion of the quaternary ammonium cation moiety.

[0090] As used herein, "aromatic acid" is an aromatic compound containing both an aromatic ring and an organic acid functional group; specifically, it refers to a compound in which one or more carboxyl groups (-COOH) are substituted on an aromatic ring having 6 to 20 carbon atoms. Therefore, "conjugate base of an aromatic acid" can refer to a compound in which one or more carboxyl groups (-COOH) are substituted on an aromatic ring having 6 to 20 carbon atoms. - Compounds containing hydrogen ions (H+) + It is provided by the carboxyl group.

[0091] In other words, X - It is an aromatic ring structure having 6 to 20 carbon atoms, wherein one or more hydroxyl groups and one or more carboxylate groups are substituted. When X - With such a structure, anionic substitution is advantageous, thus the preparation can be easy, and the antibacterial activity of the compound can be further improved.

[0092] In this respect, in addition to the hydroxyl group, the conjugate base of the aromatic acid can be further substituted with one or more (more specifically one to three) substituents selected from halogens, alkyl groups having one to four carbon atoms, haloalkyl groups having one to four carbon atoms, and alkoxy groups having one to four carbon atoms.

[0093] For example, X - It can be represented by the following chemical formula 2:

[0094] [Chemical Formula 2]

[0095]

[0096] In chemical formula 2,

[0097] A is a benzene ring or a naphthalene ring.

[0098] R can be fluorine, bromine, chlorine, iodine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, methoxy, or ethoxy.

[0099] e is 1, 2, or 3, and

[0100] f is an integer from 0 to 5.

[0101] When f is 2 or greater, two or more R are the same or different from each other.

[0102] Specifically, in chemical formula 2,

[0103] R can be fluorine, bromine, chlorine, methyl, trifluoromethyl, or methoxy.

[0104] e can be 1, 2, or 3, and

[0105] f can be 0, 1, 2 or 3.

[0106] At this point, e+f can be 1, 2, or 3.

[0107] More specifically, X - It can be represented by any of the following chemical formulas 2-1 to 2-6:

[0108] [Chemical Formula 2-1]

[0109]

[0110] [Chemical Formula 2-2]

[0111]

[0112] [Chemical Formula 2-3]

[0113]

[0114] [Chemical Formula 2-4]

[0115]

[0116] [Chemical Formula 2-5]

[0117]

[0118] [Chemical Formula 2-6]

[0119]

[0120] In chemical formulas 2-1 to 2-6,

[0121] R' can be fluorine, bromine, chlorine, methyl, trifluoromethyl, or methoxy.

[0122] g is 0, 1, or 2, and

[0123] When g is 2, the two R's are either the same or different from each other.

[0124] h is 1 or 2.

[0125] At this point, g+h can be 1, 2, or 3.

[0126] For example, X - It is selected from any of the following:

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] For example, a compound represented by chemical formula 1 can be represented by any of the following chemical formulas 1-1 to 1-4:

[0133]

[0134] In chemical formulas 1-1 to 1-4,

[0135] R'1 can be hydrogen or methyl.

[0136] L' can be methylene or ethylene.

[0137] X - Same as defined in chemical formula 1,

[0138] n is an integer from 2 to 7, and

[0139] m is an integer from 2 to 6.

[0140] In other words, in chemical formulas 1-1 to 1-4,

[0141] n can be 2, 3, 4, 5, 6 or 7, and m can be 2, 3, 4, 5 or 6.

[0142] Furthermore, the compound is selected from any of the following compounds:

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155] Meanwhile, the compound represented by chemical formula 1 can be prepared by the preparation method in reaction scheme 1 below:

[0156] [Reaction Scheme 1]

[0157]

[0158] In reaction scheme 1, X1 is a halogen, more preferably bromine or chlorine, M is an alkali metal, and the descriptions of the remaining substituents are the same as those defined in chemical formula 1.

[0159] Step 1 in reaction scheme 1 is the step of preparing quaternary ammonium salt compound A-3 by reacting tertiary amine compound A-1 with halide compound A-2, and step 2 is the step of preparing quaternary ammonium salt compound A-3 with the desired X. - The anion substitution reaction step for the halide anion of compound A-3 prepared in step 1 is described. The above preparation method will be explained in more detail in the preparation examples described later.

[0160] Furthermore, the compound exhibits excellent antimicrobial effects against microorganisms, particularly against at least one of Gram-positive and Gram-negative bacteria.

[0161] More specifically, the compound may exhibit antibacterial properties against one or more types of bacteria classified as Gram-positive. Alternatively, the compound may exhibit antibacterial properties against one or more types of bacteria classified as Gram-negative. Alternatively, the compound may exhibit antibacterial properties against one or more types of bacteria classified as Gram-negative and one or more types of bacteria classified as Gram-positive.

[0162] In this regard, the Gram-negative bacteria to which the compound can exhibit antibacterial properties may be *Proteus mirabilis* or *Escherichia coli*, and the Gram-positive bacteria to which the compound can exhibit antibacterial properties may be *Enterococcus faecalis*, but are not limited thereto. More preferably, the compound can exhibit antibacterial properties against both Gram-positive and Gram-negative bacteria. In this regard, the meaning of the compound exhibiting antibacterial properties can be confirmed by an antibacterial rate of 50% or greater measured in an antibacterial property test using absorbance as described later.

[0163] Here, *Proteus mirabilis* is a Gram-negative, rod-shaped, facultative anaerobic or aerobic bacterium distributed in various environments and capable of infecting the respiratory tract or skin of humans and animals, thereby causing urinary tract-related diseases. In particular, it is known that infection with *Proteus mirabilis* in humans can cause urinary tract infections or acute pyelonephritis. Furthermore, *Proteus mirabilis* alkalizes urine, causing ammonia excretion, which may contribute to its foul odor.

[0164] Specifically, the antibacterial properties of the compound against Escherichia coli can be evaluated by measuring absorbance, and the antibacterial rate of the compound against Escherichia coli, as calculated by Equation 1 below, can be 70% or greater.

[0165] [Equation 1]

[0166]

[0167] In this equation,

[0168] A s (A 样品 The absorbance of the culture medium containing antibacterial substances at a wavelength of 600 nm represents the absorbance of the medium.

[0169] A0(A 参照 The absorbance of pure E. coli culture medium without antibacterial substances is measured at a wavelength of 600 nm.

[0170] More preferably, the antibacterial rate of the compound against Escherichia coli, as calculated by Equation 1, can be 70% or greater, 70.6% or greater, 75.5% or greater, 80% or greater, 90% or greater, 95% or greater, 95.3% or greater, 95.8% or greater, 96% or greater, 97% or greater, 97.3% or greater, 98% or greater, 98.1% or greater, and 100% or less.

[0171] The evaluation of the antimicrobial properties of the compound against Proteus mirabilis and Enterococcus faecalis can also be carried out in the same manner as the evaluation of the antimicrobial properties of the compound against Escherichia coli.

[0172] Antibacterial agents

[0173] Meanwhile, according to another aspect, an antimicrobial agent comprising the compound represented by Chemical Formula 1 is provided. The antimicrobial agent may comprise the compound described above, which has excellent bacterial growth inhibition effects, thereby exhibiting excellent antimicrobial properties.

[0174] In this regard, antimicrobial agents can be mixed into products requiring antimicrobial properties, or applied or coated onto said products. They can be applied to a variety of household chemical products in which harmful bacteria can easily grow, such as, but not limited to, products requiring such antimicrobial properties, such as humidifiers, water tanks, refrigerators, air purifiers, aquariums, air purifiers, agricultural films, preservation materials, containers for processed food, and packaging materials for electronic components.

[0175] Furthermore, depending on the desired application, antimicrobial agents containing the compounds can be prepared in various forms, such as antimicrobial coating compositions, antimicrobial resins, antimicrobial plastics, etc. Additionally, the antimicrobial agent may contain other types of resins and / or solvents to facilitate its mixing with or application to antimicrobial articles.

[0176] In the following description, the effects and functions of the invention will be described in more detail with reference to specific exemplary embodiments thereof. However, these exemplary embodiments are provided for illustrative purposes only, and the scope of the invention is not limited thereto.

[0177] Preparation Example A: Preparation of Compound A

[0178]

[0179] 7.86 g of 2-(dimethylamino)ethyl methacrylate and 11.06 g of bromodecane were added to 30 mL of acetonitrile (ACN) and stirred. Then, 4 mg of p-methoxyphenol (4-methoxyphenol; MeHQ) was added, and the mixture was allowed to reflux at 60 °C for 24 hours. After the reaction was complete, the product was added to 300 mL of diethyl ether, precipitated by stirring, and filtered to obtain compound A. MALDI-TOF mass spectra of the obtained compound A and... 1 The 1H NMR analysis detected a value corresponding to the cation of compound A. Simultaneously, the MS spectrum of compound A and... 1 The H NMR spectra are shown in... Figure 1 and Figure 2 middle.

[0180] [MS-H] + =298

[0181] 1H NMR (500MHz, DMSO-d6, δ[ppm]): 6.08(1H), 5.77(1H), 4.52(2H), 3.69(2H), 3.35(2H), 3.09(6H), 1.91(3H), 1.67(2H), 1.25(14H), 0.96(3H)

[0182] Preparation Example B: Preparation of Compound B

[0183]

[0184] Compound B was synthesized in the same manner as in Preparation Example A, except that bromooctane was used instead of bromodecane in Preparation Example A.

[0185] [MS-H] + =270

[0186] Preparation Example C: Preparation of Compound C

[0187]

[0188] Compound C was synthesized in the same manner as in Preparation Example A, except that bromododecane was used instead of bromodecane in Preparation Example A.

[0189] [MS-H] + =326

[0190] Preparation Example D: Preparation of Compound D

[0191]

[0192] 7.16 g of 2-(dimethylamino)ethyl acrylate and 11.06 g of bromodecane were added to 30 mL of acetonitrile (ACN) and stirred. Then, 4 mg of p-methoxyphenol (MeHQ) was added, and the mixture was allowed to reflux at 60 °C for 24 hours. After the reaction was complete, the product was added to 250 mL of diethyl ether, and the precipitate was obtained by stirring and filtration to obtain compound D. MALDI-TOF mass spectra of the obtained compound D and... 1 The results of H NMR analysis showed that the value corresponding to the cation of compound D was detected.

[0193] [MS-H] + =284

[0194] 1H NMR (500MHz, DMSO-d6, δ[ppm]): 6.48(1H), 6.11(1H), 5.94(1H), 4.67(2H), 4.13(2H), 3.58(2H), 3.48(6H), 1.74(2H), 1.27(14H), 0.86(3H)

[0195] Preparation Example E: Preparation of Compound E

[0196]

[0197] Compound E was synthesized in the same manner as in Preparation Example D, except that bromooctane was used instead of bromodecane in Preparation Example D.

[0198] [MS-H] + =256

[0199] Preparation Example 1: Preparation of Compound 1

[0200]

[0201] 20 g of compound A synthesized in Preparation Example A was dissolved in 100 mL of DI water, and 11.3 g of sodium salicylate dissolved in 50 mL of water was mixed and stirred at room temperature for 24 hours to carry out anionic substitution reaction. The organic layer was then extracted from the reaction product with ethyl acetate (EA) / DI water to remove the solvent, and recrystallized with EA to obtain compound 1. 1 The 1H NMR analysis revealed a peak corresponding to the anion of compound 1, and as an inorganic analysis result, compound 1 showed a significantly lower Br content compared to compound A, indicating that substitution occurred normally. Meanwhile, compound 1... 1 The H NMR and mass spectra are shown in the figures. Figure 3 and Figure 4 The results of measuring the Br content of compound 1 and compound A using combustion ion chromatography (C-IC) are shown in Table 1 below.

[0202] [MS-H] + =298

[0203] [MH] - =137

[0204] 1H NMR (500MHz, DMSO-d6, δ[ppm]): 7.63(1H), 7.09(1H), 6.58(2H), 6.08(1H), 5.76(1H), 4.53(2H), 3.69(2H), 3.32(2H), 3.08(6H), 1.91(3H), 1.67(2H), 1.25(14H), 0.86(3H)

[0205] [Table 1]

[0206] Compound A 15.4 Compound 1 2.2

[0207] Preparation Example 2: Preparation of Compound 2

[0208]

[0209] Compound 2 was synthesized in the same manner as in Preparation Example 1, except that Compound C prepared in Preparation Example C was used instead of Compound A in Preparation Example 1.

[0210] [MS-H] + =326

[0211] [MH] - =137

[0212] Preparation Example 3: Preparation of Compound 3

[0213]

[0214] Compound 3 was synthesized in the same manner as in Preparation Example 1, except that compound F (N-(2-(acryloyloxy)ethyl)-N,N-dimethyldodecane-1-ammonium bromide) was used instead of compound A in Preparation Example 1.

[0215] [MS-H] + =312

[0216] [MH] - =137

[0217] Preparation Example 4: Preparation of Compound 4

[0218]

[0219] Compound 4 was synthesized in the same manner as in Preparation Example 1, except that compound B prepared in Preparation Example B was used instead of compound A, and sodium vanillate was used instead of sodium salicylate in Preparation Example 1.

[0220] [MS-H] + =284

[0221] [MH]- =167

[0222] Preparation Example 5: Preparation of Compound 5

[0223]

[0224] Compound 5 was synthesized in the same manner as in Preparation Example 1, except that compound D prepared in Preparation Example D was used instead of compound A, and sodium vanillate was used instead of sodium salicylate in Preparation Example 1.

[0225] [MS-H] + =256

[0226] [MH] - =167

[0227] Preparation Example 6: Preparation of Compound 6

[0228]

[0229] Compound 6 was synthesized in the same manner as in Preparation Example 1, except that Compound E prepared in Preparation Example E was used instead of Compound A, and sodium vanillate was used instead of sodium salicylate in Preparation Example 1.

[0230] [MS-H] + =284

[0231] [MH] - =167

[0232] Experimental Example - Evaluation of Antibacterial Properties

[0233] Unless otherwise stated, the following characteristic assessments were conducted under constant temperature and humidity (23±1℃, relative humidity 50±10%).

[0234] (1) Evaluation of antibacterial properties against Escherichia coli

[0235] 25 mL of nutrient broth inoculated with Escherichia coli (ATCC 25922) at 3000 CFU / mL was transferred to a 50 mL conical tube. The antimicrobial compound (bacteriostatic substance) prepared in the preparation and comparative preparation examples was then injected in the amounts described in Table 2 below, followed by thorough mixing. The tube was then incubated for 16 hours in a shaking incubator (Visiontech, VS-37SIF) maintained at 35°C.

[0236] The incubated solution was diluted to 1 / 5 using 1×PBS buffer, and the absorbance of the diluted solution at 600 nm was measured using a UV-Vis spectrophotometer (KLab, Optizen POP). Additionally, *E. coli* (ATCC 25922) was prepared as a control and cultured for 16 hours in a shaking incubator (VISIONTECH, VS-37SIF) at 35°C in pure culture medium without antimicrobial compounds; its absorbance at 600 nm was measured in the same manner as above.

[0237] Then, the antibacterial rate (%) against Escherichia coli (ATCC 25922) was calculated according to Equation 1 below, and the results are shown in Table 2 below.

[0238] [Equation 1]

[0239]

[0240] In this equation,

[0241] A s (A 样品 The absorbance of the culture medium containing antibacterial substances at a wavelength of 600 nm represents the absorbance of the medium.

[0242] A0(A 参照 The absorbance of pure E. coli culture medium without antibacterial substances is measured at a wavelength of 600 nm.

[0243] [Table 2]

[0244]

[0245] Referring to Table 2, it can be seen that the compounds of the examples having conjugate bases of aromatic acids exhibit improved antibacterial properties against *Escherichia coli* compared to the compounds of the comparative examples, each having a halide anion. In particular, when comparing (compound 4 of Example 4 and compound B of Comparative Example 1) and (compound 6 of Example 6 and compound E of Comparative Example 2), it was found that the compounds of the examples having conjugate bases of aromatic acids as anions showed significantly higher antibacterial rates, even though they had the same cationic structure.

[0246] Therefore, it can be seen that the compound represented by chemical formula 1, in which a quaternary ammonium cation and an anion of a conjugate base of an aromatic acid are combined, exhibits excellent antibacterial properties against at least one of Gram-positive and Gram-negative bacteria.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In chemical formula 1, Y is O, L represents methylene, ethylene, or propylene. R1 is hydrogen or methyl. R2 and R3 are hydrogen. One of R4 to R6 is an alkyl group having 10 to 12 carbon atoms, and the others are each independently methyl or ethyl. X - Represented by the following chemical formula 2-3: [Chemical Formula 2-3] In chemical formula 2-3, R' is a methoxy group. g is 1 or 2.

2. The compound according to claim 1, Where X - for: 。 3. The compound according to claim 1, The compound represented by chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: In chemical formulas 1-1 to 1-4, R'1 is hydrogen or methyl. L' represents methylene or ethylene. X - Same as that defined in claim 1, n is 4 or 5, and m is 4.

4. The compound according to claim 1, The compound mentioned is selected from any of the following compounds: 。 5. The compound according to claim 1, The compound described therein exhibits antibacterial properties against one or more of Gram-positive and Gram-negative bacteria.

6. The compound according to claim 5, The Gram-negative bacteria mentioned above are Proteus mirabilis or Escherichia coli, and The Gram-positive bacteria is Enterococcus faecalis.

7. The compound according to claim 5, The compound described therein exhibits antibacterial properties against both Gram-positive and Gram-negative bacteria.

8. An antibacterial agent comprising the compound according to any one of claims 1 to 7.

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