Organic compounds and their preparation methods, bactericides and purification devices

Abstract

This application relates to an organic compound and its preparation method, a bactericide, and a purification device. The organic compound has the general formula (I): ; wherein, L is selected from at least one of a single bond, a C1-C8 alkylene group, and a C2-C8 alkoxyacyl group; R1 and R2 are each independently selected from at least one of hydrogen, substituted or unsubstituted C1-C8 alkyl groups; or, R1 and R2 and the C atom connected to them together form a C3-C8 cycloalkyl group. The organic compound of this application contains an amide bond, and the amide bond is connected to the R-configured carbon atom, exhibiting bactericidal activity, particularly effective in inhibiting the activity of *Escherichia coli* and *Staphylococcus aureus*, and possessing good bactericidal stability without producing toxic substances.

Description

Technical Field

[0001] This application relates to the field of compound technology, and in particular to an organic compound and its preparation method, a bactericide and a purification device. Background Technology

[0002] Air contains a large number of microorganisms, including bacteria (containing endotoxins), fungi (containing fungal spores), and viruses. These microorganisms typically attach to particles of a certain size, such as dust and droplet nuclei, forming aerosols suspended in the air. These aerosols are then transmitted through the air, making air a significant transmission medium and potentially causing various poisonings, infections, allergies, and infectious diseases. Consequently, the demand for air disinfection has surged. Traditional disinfection methods primarily utilize the chemical properties of substances like chlorine and ozone, but these methods have significant drawbacks—they generate large amounts of toxic compounds, posing a serious threat to the environment and human health; while other disinfectants are less effective.

[0003] Therefore, it is necessary to improve traditional technologies. Summary of the Invention

[0004] Based on this, this application provides an organic compound with good bactericidal effect, its preparation method, bactericide and purification device.

[0005] The technical solution to the above-mentioned technical problems in this application is as follows.

[0006] An organic compound having the general formula shown in formula (I):

[0007]

[0008] Wherein, L is selected from at least one of single bonds and C1-C8 alkylene groups;

[0009] R1 and R2 are each independently selected from at least one of hydrogen, substituted or unsubstituted C1-C8 alkyl and C2-C8 alkoxyacyl groups; or, R1 and R2 and the C atom connected to them together form a C3-C8 cycloalkyl group.

[0010] In some embodiments, in the organic compound, the substituents in the substituted C1-C8 alkyl group include hydroxyl groups, substituted or unsubstituted indole groups, and substituted or unsubstituted C6-C8 alkyl groups. 20 Aromatic group and at least one of substituted or unsubstituted C3-C8 cycloalkyl groups.

[0011] In some embodiments, the substituted or unsubstituted indole group, the substituted or unsubstituted C6-C6 group, in the organic compound... 20The aromatic group and the substituents in the substituted or unsubstituted C3-C8 cycloalkyl group include C1-C6 alkyl, C2-C6 alkenyl, hydroxyl, and C7-C6 cycloalkyl groups. 16 At least one of arylalkoxy, halogen and nitro.

[0012] In some embodiments, in the organic compound, the substituent in the substituted or unsubstituted indole group includes at least one of C1-C6 alkyl and C2-C6 alkenyl groups; and / or

[0013] The substituted or unsubstituted C6~C 20 Substituents in aromatic groups include hydroxyl groups, C7~C6 substituents, and C7~C6 substituents. 16 At least one of arylalkoxy, halogen and nitro.

[0014] In some embodiments, in the organic compound, R1 is hydrogen, and R2 is selected from hydrogen, C2 alkoxyacyl, or a structure of formula (II-1) to (II-10):

[0015]

[0016] Alternatively, R1 and R2, along with the C atoms connected to them, form a cyclobutyl group.

[0017] In some of these embodiments, L in the organic compound is selected from a single bond and an ethylene.

[0018] In some embodiments, the organic compound is selected from the structures of formulas (III-1) to (III-12):

[0019]

[0020] Accordingly, a method for preparing an organic compound is provided, comprising the following steps:

[0021] A condensation reaction was carried out by mixing (R)-3-phenyl-2-hydroxypropionic acid and the compound shown in formula (IV) to produce the compound of formula (I):

[0022]

[0023] In equations (I) and (IV),

[0024] L is selected from at least one of single bonds and C1-C8 alkylene groups;

[0025] R1 and R2 are each independently selected from at least one of hydrogen, substituted or unsubstituted C1-C8 alkyl and C2-C8 alkoxyacyl groups; or, R1 and R2 and the C atom connected to them together form a C3-C8 cycloalkyl group.

[0026] In some embodiments, in the method of preparing the organic compound, the compound represented by formula (IV) includes at least one of the structures of formulas (IV-1) to (IV-10):

[0027] .

[0028] In some embodiments, in the method for preparing the organic compound, the condensation reaction is carried out in the presence of a catalyst, the catalyst comprising at least one of HOBT, EDCI, and DIPEA; and / or

[0029] The solvent for the condensation reaction includes DCM.

[0030] This application provides, on the one hand, the application of the above-mentioned organic compounds or the organic compounds prepared by the above-mentioned methods in the preparation of bactericides.

[0031] Another aspect of this application provides a bactericide, comprising the above-described organic compound or an organic compound prepared by the above-described preparation method.

[0032] This application also provides a purification article comprising the above-mentioned bactericide.

[0033] Compared with the prior art, the organic compounds of this application have the following beneficial effects:

[0034] The organic compound of this application contains an amide bond, and the amide bond is connected to an R-configured carbon atom, which has a bactericidal effect, especially effectively inhibiting the activity of Escherichia coli and Staphylococcus aureus, and has good bactericidal stability and does not produce toxic substances. Attached Figure Description

[0035] To more clearly illustrate the technical solutions in the specific embodiments of this application or the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of this application. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0036] Figure 1 The proton NMR spectrum of the compound of formula (III-1) prepared in Example 1;

[0037] Figure 2 The proton spectrum of the compound of formula (III-2) prepared in Example 2;

[0038] Figure 3 The proton spectrum of the compound of formula (III-3) prepared in Example 3;

[0039] Figure 4The proton NMR spectrum of the compound of formula (III-4) prepared in Example 4;

[0040] Figure 5 The proton NMR spectrum of the compound of formula (III-5) prepared in Example 5;

[0041] Figure 6 The proton NMR spectrum of the compound of formula (III-6) prepared in Example 6;

[0042] Figure 7 The proton NMR spectrum of the compound of formula (III-7) prepared in Example 7;

[0043] Figure 8 The proton NMR spectrum of the compound of formula (III-8) prepared in Example 8;

[0044] Figure 9 The proton NMR spectrum of the compound of formula (III-9) prepared in Example 9;

[0045] Figure 10 The proton NMR spectrum of the compound of formula (III-10) prepared in Example 0;

[0046] Figure 11 The proton NMR spectrum of the compound of formula (III-11) prepared in Example 11;

[0047] Figure 12 The proton spectrum of the compound of formula (III-12) prepared in Example 12. Detailed Implementation

[0048] Reference will now be made to detailed embodiments of this application, one or more of which are described below. Each example is provided for explanation and not for limitation of this application. In fact, it will be apparent to those skilled in the art that various modifications and variations can be made to this application without departing from its scope or spirit. For example, features described or illustrated as part of one embodiment may be used in another embodiment to produce further embodiments.

[0049] Therefore, this application is intended to cover such modifications and variations falling within the scope of the appended claims and their equivalents. Other objects, features, and aspects of this application are disclosed in or will be apparent from the following detailed description. It will be understood by those skilled in the art that this discussion is merely a description of exemplary embodiments and is not intended to limit the broader aspects of this application.

[0050] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the application.

[0051] The terms “comprising,” “including,” or any other variations thereof are intended to cover non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements includes not only those elements but also other elements not expressly listed, or elements inherent to such a process, method, article, or apparatus. Without further limitation, an element preceded by the phrase “comprising one…” does not exclude the presence of other identical elements in the process, method, article, or apparatus that includes said element. The indefinite articles “a” and “an” preceding an element or component in this application are not restrictive in terms of the quantity (i.e., the number of times) of the element or component. Therefore, “an” or “a” should be interpreted as including one or at least one, and singular elements or components also include plural forms, unless the quantity clearly refers only to the singular. “A plurality” means at least two, such as two, three, etc., unless otherwise expressly specified.

[0052] The weights of the relevant components mentioned in the embodiments of this application can refer not only to the specific content of each component, but also to the proportional relationship between the weights of the components. Therefore, any scaling up or down of the content of the relevant components according to the embodiments of this application is within the scope disclosed in the embodiments of this application. Specifically, the weights mentioned in the embodiments of this application can be well-known units of mass in the chemical industry, such as μg, mg, g, and kg.

[0053] Unless otherwise shown or indicated in the operational embodiments, all figures used to represent the amounts, physicochemical properties, etc., of ingredients in the specification and claims are to be understood to be adjusted by the term "about" in all cases. For example, therefore, unless stated to the contrary, the numerical parameters listed in the foregoing specification and appended claims are approximations, and those skilled in the art can appropriately modify these approximations to obtain the desired characteristics by utilizing the teachings disclosed herein. The use of numerical ranges indicated by endpoints includes all numbers within that range and any range within that range; for example, 1 to 5 includes 1, 1.1, 1.3, 1.5, 2, 2.75, 3, 3.80, 4, and 5, etc.

[0054] In this application, "substitution" means that the hydrogen atom in the substituent is replaced by the substituent, and adjacent groups can form aliphatic, aromatic or heteroaromatic ring systems with each other.

[0055] In this application, "substituted or unsubstituted" means that the defined group may or may not be substituted. When the defined group is substituted, it should be understood that it may be substituted by a group acceptable in the art. Including but not limited to: C1~C 20 Alkyl, heterocyclic groups containing 3 to 20 ring atoms, aryl groups containing 5 to 20 ring atoms, heteroaryl groups containing 5 to 20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, -NRR′, cyano, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, nitro, or halogen, and the above groups may be further substituted with substituents acceptable in the art; it is understood that R and R′ in -NRR′ are each independently substituted with groups acceptable in the art, including but not limited to H, C1-C6 alkyl, cycloalkyl containing 3-8 ring atoms, heterocyclic group containing 3-8 ring atoms, aryl group containing 5-20 ring atoms, or heteroaryl group containing 5-10 ring atoms; C1-C6 alkyl, cycloalkyl containing 3-8 ring atoms, heterocyclic group containing 3-8 ring atoms, aryl group containing 5-20 ring atoms, or heteroaryl group containing 5-10 ring atoms may optionally be further substituted by one or more of the following groups: C1-C6 alkyl, cycloalkyl containing 3-8 ring atoms, heterocyclic group containing 3-8 ring atoms, halogen, hydroxyl, nitro or amino.

[0056] In this application, "ring atom number" refers to the number of atoms in the ring itself of a structural compound obtained by atomic bonding to form a ring (e.g., monocyclic compound, fused ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. For example, a benzene ring has 6 ring atoms, a naphthalene ring has 10 ring atoms, and a thiophene group has 5 ring atoms.

[0057] Aromatic groups refer to hydrocarbon groups containing at least one aromatic ring. Heteroaromatic groups refer to aromatic hydrocarbon groups containing at least one heteroatom. Heteroatoms are preferably selected from Si, N, P, O, S, and / or Ge, and particularly preferably from Si, N, P, O, and / or S. Fused-ring aromatic groups refer to aromatic groups whose rings may have two or more rings, wherein two carbon atoms are shared by two adjacent rings, i.e., fused rings. Fused-heterocyclic aromatic groups refer to fused-ring aromatic hydrocarbon groups containing at least one heteroatom. For the purposes of this application, aromatic groups or heteroaromatic groups include not only systems with aromatic rings but also non-aromatic ring systems. Therefore, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetraazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc., are also considered aromatic groups or heterocyclic aromatic groups for the purposes of this application. For the purposes of this application, fused-ring aromatic or fused-heterocyclic aromatic ring systems not only include systems containing aromatic or heterocyclic aromatic groups, but also systems in which multiple aromatic or heterocyclic aromatic groups can be interrupted by short non-aromatic units (<10% non-H atoms, preferably less than 5% non-H atoms, such as C, N, or O atoms). Therefore, systems such as 9,9'-spirodifluorene, 9,9-diarylfluorene, triarylamines, and diaryl ethers are also considered fused-ring aromatic ring systems for the purposes of this application.

[0058] Specifically, examples of fused-ring aromatic groups include: naphthalene, anthracene, fluoranthene, phenanthrene, benzo[a]phenanthrene, dinaphthalene-benzene, tetraphenylene, pyrene, benzo[a]pyrene, acenaphthene, fluorene, and their derivatives.

[0059] Specifically, examples of fused heterocyclic aromatic groups include: benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanolopyrrole, furanolofuran, thienofuran, benzoisoxazole, benzoisothiazazole, quinoline, isoquinoline, o-diazonine, quinoxaline, phenanthridine, primidine, quinazoline, quinazoline, and their derivatives.

[0060] In this application, aromatic groups, aromatic compounds, and aromatic ring systems have the same meaning and can be used interchangeably.

[0061] In this application, heteroaromatic groups, heteroaromatic compounds, and heteroaromatic ring systems have the same meaning and can be used interchangeably.

[0062] In this application, "adjacent groups" means groups bonded to the same carbon atom or to adjacent carbon atoms. These definitions apply accordingly to "adjacent substituents".

[0063] One embodiment of this application provides an organic compound having the general formula as shown in formula (I):

[0064]

[0065] Wherein, L is selected from at least one of single bonds and C1-C8 alkylene groups;

[0066] R1 and R2 are each independently selected from at least one of hydrogen, substituted or unsubstituted C1-C8 alkyl and C2-C8 alkoxyacyl groups; or, R1 and R2 and the C atom connected to them together form a C3-C8 cycloalkyl group.

[0067] The organic compound of this application contains an amide bond, and the amide bond is connected to an R-configured carbon atom, which has a bactericidal effect, especially effectively inhibiting the activity of Escherichia coli and Staphylococcus aureus, and has good bactericidal stability and does not produce toxic substances.

[0068] C1~C8 alkylene refers to a saturated hydrocarbon group containing 1 to 8 carbon atoms, and the divalent group formed by removing one hydrogen atom from each of the two ends of the hydrocarbon group. The following is a detailed description:

[0069] C1 alkylene: namely methylene, chemical formula -CH2-;

[0070] C2 alkylene: is 1,2-ethylene, with the chemical formula -CH2CH2-, also known as ethylene group;

[0071] C3 alkylene: There are two structures, namely 1,2-propylene-CH2CH2CH2- and 1,3-propylene-CH2CH(CH3)-;

[0072] C4 alkylene compounds include 1,2-butylene-CH2CH2CH2CH2-, 1,3-butylene-CH2CH2CH(CH3)-, 1,4-butylene-CH2CH(CH3)CH2-, 2,3-butylene-CH(CH3)CH(CH3)-, etc.

[0073] C5 alkylene groups include 1,2-pentylene-CH2CH2CH2CH2CH2-, 1,3-pentylene-CH2CH2CH2CH(CH3)-, 1,4-pentylene-CH2CH2CH(CH3)CH2-, 1,5-pentylene-CH2CH(CH3)CH2CH2-, 2,3-pentylene-CH2CH(CH3)CH(CH3)-, 2,4-pentylene-CH(CH3)CH2CH(CH3)-, etc.

[0074] C6 alkylene groups include 1,2-hexylene-CH2CH2CH2CH2CH2CH2-, 1,3-hexylene-CH2CH2CH2CH2CH(CH3)-, 1,4-hexylene-CH2CH2CH2CH(CH3)CH2-, 1,5-hexylene-CH2CH2CH(CH3)CH2CH2-, 1,6-hexylene-CH2CH(CH3)CH2CH2CH2-, 2,3-hexylene-CH2CH(CH3)CH2CH(CH3)-, 2,4-hexylene-CH2CH(CH3)CH(CH3)CH2-, 2,5-hexylene-CH(CH3)CH2CH(CH3)CH2-, and 3,4-hexylene-CH2CH(CH2CH3)CH(CH3)-, etc.

[0075] C7 alkylene compounds include 1,2-heptene-CH2CH2CH2CH2CH2CH2CH2-, 1,3-heptene-CH2CH2CH2CH2CH2CH(CH3)-, 1,4-heptene-CH2CH2CH2CH2CH(CH3)CH2-, and so on, and many other structures can be written.

[0076] C8 alkylene groups include 1,2-octylene-CH2CH2CH2CH2CH2CH2CH2CH2-, 1,3-octylene-CH2CH2CH2CH2CH2CH2CH(CH3)-, and 1,4-octylene-CH2CH2CH2CH2CH2CH(CH3)CH2-.

[0077] C2~C8 alkoxyacyl groups are groups consisting of an acyl group (-CO-) and a C1~C7 alkoxy group (-OR, where R is a C1~C7 alkyl group), with the general formula RO-CO-. For example, when R is methyl, we get methoxycarbonyl (CH3-O-CO-), which is a C2 alkoxyacyl group.

[0078] C1-C8 alkyl refers to a saturated hydrocarbon group containing 1 to 8 carbon atoms, including but not limited to one of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, and octyl.

[0079] In some of these examples, the substituents in the substituted C1-C8 alkyl groups include hydroxyl groups, substituted or unsubstituted indole groups, and substituted or unsubstituted C6-C8 alkyl groups. 20 Aromatic group and at least one of substituted or unsubstituted C3-C8 cycloalkyl groups.

[0080] It is understandable that the indole group is the part remaining after removing a hydrogen atom from the indole molecule;

[0081] Aromatic groups are the collective term for monovalent groups remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule;

[0082] Cycloalkyl refers to alkyl groups with a cyclic carbon skeleton. Their carbon atoms are linked by single bonds to form a ring, and each carbon atom, except for the ring-forming chemical bond, is saturated with hydrogen atoms; including but not limited to cyclopropyl, cyclobutyl, and cyclopentyl.

[0083] Furthermore, it can be understood that the substituted C1-C8 alkyl groups include hydroxyl-substituted C1-C8 alkyl groups, indole-substituted C1-C8 alkyl groups, and C6-C8 alkyl groups. 20 At least one of aryl-substituted C1-C8 alkyl groups and C1-C8 substituted C3-C8 cycloalkyl groups; further, the indole group in the indole-substituted C1-C8 alkyl group may be further substituted; C6-C 20 The aromatic groups in the aromatic-substituted C1-C8 alkyl groups can be further substituted; the cycloalkyl groups in the C1-C8 alkyl groups substituted C3-C8 alkyl groups can be further substituted.

[0084] In some of these examples, the substituents in the substituted C1-C8 alkyl groups include hydroxyl groups, substituted or unsubstituted indole groups, and substituted or unsubstituted C6-C8 alkyl groups. 12 Aromatic group and at least one of substituted or unsubstituted C5-C7 cycloalkyl groups.

[0085] In some of these examples, the organic compound contains a substituted or unsubstituted indole group, or a substituted or unsubstituted C6~C... 20 The aryl group and the substituents in the substituted or unsubstituted C3-C8 cycloalkyl groups include C1-C6 alkyl, C2-C6 alkenyl, hydroxyl, and C7-C6 cycloalkyl groups. 16 At least one of arylalkoxy, halogen and nitro.

[0086] It can be understood that C2~C6 alkenyl groups refer to unsaturated hydrocarbon groups containing carbon-carbon double bonds (C=C) and having 2 to 6 carbon atoms, with the general formula C. n H 2n -1 (n=2~6), these are the groups remaining after removing one hydrogen atom from an olefin molecule;

[0087] C7~C 16 Arylalkoxy groups are formed by chemical bonds between aryl groups (groups containing aromatic structures such as benzene rings) and alkoxy groups (composed of alkyl groups connected to oxygen atoms, with the general formula -OR, where R is an alkyl group), and the total number of carbon atoms in the group is between 7 and 16.

[0088] Halogens include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

[0089] Further, the substituents in the substituted or unsubstituted indole group include at least one of C1-C6 alkyl and C2-C6 alkenyl groups. Further, the substituents in the substituted or unsubstituted indole group include at least one of C1-C3 alkyl and C4-C6 alkenyl groups.

[0090] Furthermore, substituted or unsubstituted C6~C 20 Substituents in aromatic groups include hydroxyl groups, C7~C6 substituents, and C7~C6 substituents. 16 At least one of arylalkoxy, halogen, and nitro groups. Further, substituted or unsubstituted C6~C... 20 Substituents in aromatic groups include hydroxyl groups, C7~C6 substituents, and C7~C6 substituents. 10 At least one of arylalkoxy, halogen and nitro.

[0091] In some of these examples, in the organic compound, R1 is at least one of hydrogen, substituted or unsubstituted C1-C4 alkyl and C2-C4 alkoxyacyl; or, R1 and R2 and the C atom connected to them together form a C3-C5 cycloalkyl.

[0092] Furthermore, in some of these examples, in the organic compound, R1 is at least one of hydrogen, substituted or unsubstituted C1-C2 alkyl and C2-C3 alkoxyacyl; or, R1 and R2 and the C atom connected to them together form a C4-C5 cycloalkyl.

[0093] In some of these examples, in the organic compound, R1 is hydrogen, and R2 is selected from hydrogen, C2 alkoxyacyl, or one of the structures of formulas (II-1) to (II-10):

[0094]

[0095] Alternatively, R1 and R2, along with the C atoms connected to them, form a cyclobutyl group.

[0096] In some of these examples, in the organic compound, L is selected from either a single bond or an ethylene.

[0097] In some of these examples, the organic compound is selected from one of the structures of formulas (III-1) to (III-12):

[0098]

[0099] One embodiment of this application provides a method for preparing an organic compound, comprising the following steps:

[0100] A condensation reaction was carried out by mixing (R)-3-phenyl-2-hydroxypropionic acid and the compound shown in formula (IV) to produce the compound of formula (I):

[0101]

[0102] In equations (I) and (IV),

[0103] L is selected from at least one of single bonds and C1-C8 alkylene groups;

[0104] R1 and R2 are each independently selected from at least one of hydrogen, substituted or unsubstituted C1-C8 alkyl and C2-C8 alkoxyacyl groups; or, R1 and R2 and the C atom connected to them together form a C3-C8 cycloalkyl group.

[0105] In the preparation method of organic compounds, the carboxyl group of (R)-3-phenyl-2-hydroxypropionic acid and the amino group of the compound shown in formula (IV) undergo condensation to generate compound (I); this compound contains an amide bond, and the amide bond is connected to the carbon atom of the R configuration, which has a bactericidal effect, especially effectively inhibiting the activity of Escherichia coli and Staphylococcus aureus, and has good bactericidal stability and does not produce toxic substances.

[0106] The organic compounds in this application use inexpensive and readily available raw materials, and the preparation process is simple.

[0107] It is understood that the above-mentioned organic compounds can be prepared by the method for preparing organic compounds provided in this application, and the method for preparing organic compounds provided in this application can be used to prepare the above-mentioned organic compounds. The characteristics of the organic compounds provided in this application and the organic compounds can be mutually applied.

[0108] It is understandable that (R)-3-phenyl-2-hydroxypropionic acid, with the English name (R)-2-Hydroxy-3-phenylpropanoic acid, has the structure shown in formula (V):

[0109] .

[0110] In some of these examples, the molar ratio of (R)-3-phenyl-2-hydroxypropionic acid and the compound shown in formula (IV) is 1 to 1.2:1 in the preparation of the organic compound.

[0111] In some of these examples, the organic compound is prepared in a manner in which the compound represented by formula (IV) includes at least one of the structures of formulas (IV-1) to (IV-10):

[0112] .

[0113] In some of these examples, the condensation reaction in the preparation of the organic compound is carried out in the presence of a catalyst, including at least one of HOBT (1-hydroxybenzotriazole), EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide), and DIPEA (N,N-diisopropylethylamine).

[0114] In some of these examples, the catalysts used in the preparation of organic compounds include HOBT, EDCI, and DIPEA.

[0115] HOBT, EDCI, and DIPEA promote the condensation of acid and amine. Specifically, under the catalysis of DIPEA, EDCI first reacts with the acid "(R)-3-phenyl-2-hydroxypropionic acid" to form an intermediate, which is then rapidly converted into an active ester under the action of HOBT. The amine "compound of formula (IV)," acting as a nucleophile, attacks the active ester to obtain the target amine. The presence of HOBT facilitates the reaction, and the generated byproduct urea is water-soluble and easily removed.

[0116] Further, the molar ratio of HOBT, EDCI, DIPEA to (R)-3-phenyl-2-hydroxypropionic acid is 1~1.2:1~1.2:1~1.2:1. Optionally, the molar ratio of HOBT, EDCI, DIPEA to (R)-3-phenyl-2-hydroxypropionic acid is 1:1:1:1.

[0117] In some of these examples, the solvent for the condensation reaction in the preparation of the organic compound includes DCM (dichloromethane).

[0118] In some of these examples, the condensation reaction temperature in the preparation of the organic compounds is 15°C to 40°C.

[0119] In some examples, the method for preparing organic compounds includes a post-processing step of the reaction solution obtained after the condensation reaction is completed:

[0120] The solvent in the reaction solution is removed to obtain a solid phase;

[0121] The solid phase was extracted using an organic solvent and water, and the organic phase was then subjected to chromatography.

[0122] Furthermore, organic solvents include DCM.

[0123] Furthermore, the chromatographic process includes column chromatography.

[0124] It is understood that the compounds shown in formulas (IV-1) to (IV-10) can be purchased commercially or prepared at home.

[0125] In some of these examples, the preparation of the organic compound represented by formula (IV-1) includes the following steps:

[0126] N-dimethylpropenyl-substituted indole intermediate was prepared by mixing (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indole-3-yl)propionate, 1-bromo-3-methylbutene base and organic solvent for substitution reaction.

[0127] Under acidic conditions, the N-dimethylpropenyl-substituted indole intermediate was subjected to deBoc group treatment to prepare the compound shown in formula (IV-1).

[0128] In some of these examples, the preparation of the compound shown in formula (IV-1) includes the following steps: (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionate salt.

[0129] The amino group at the 2-position of (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indole-3-yl)propionate was protected with Boc2O to prepare (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indole-3-yl)propionate.

[0130] Furthermore, amino protection is carried out under alkaline conditions controlled by NaOH or NaHCO3, and in a mixed solvent of dioxane and water.

[0131] In some of these examples, the preparation of the organic compound represented by formula (IV-2) includes the following steps:

[0132] An N-methyl-substituted indole intermediate was prepared by mixing (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indole-3-yl)propionic acid, CH3I, a base and an organic solvent and carrying out a substitution reaction.

[0133] Under acidic conditions, the N-methyl-substituted indole intermediate was subjected to deBoc group treatment to prepare the compound shown in formula (IV-2).

[0134] In some examples, the preparation steps of the compound shown in formula (IV-2) involve first dissolving (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indole-3-yl)propionic acid in an organic solvent, followed by the addition of CH3I and a base. Further, (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indole-3-yl)propionic acid and the organic solvent are mixed and stirred at -5°C to 10°C to dissolve (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indole-3-yl)propionic acid in the organic solvent.

[0135] Furthermore, in the preparation steps of the compound shown in formula (IV-2), the base includes, but is not limited to, KOH; furthermore, the organic solvent includes, but is not limited to, DMSO. Furthermore, the temperature of the substitution reaction is 15℃~40℃.

[0136] In some of these examples, the acid used in the deBoc treatment of the compound shown in formula (IV-2) includes, but is not limited to, at least one of trifluoroacetic acid (TFA), hydrochloric acid (HCl), formic acid, and p-toluenesulfonic acid.

[0137] Similarly, the same post-treatment steps described above for the condensation reaction can be used to post-treat the reaction solution obtained from the substitution reaction.

[0138] The method for preparing organic compounds provided in this application yields organic compounds with high yields and few byproducts.

[0139] One embodiment of this application provides the use of the above-described organic compound or the organic compound prepared by the above-described preparation method in the preparation of a bactericide. Another embodiment of this application provides a bactericide comprising the above-described organic compound or the organic compound prepared by the above-described preparation method.

[0140] The bactericides prepared using the above-mentioned organic compounds or the organic compounds prepared by the above-mentioned methods have good bactericidal ability, especially effective in inhibiting the activity of Escherichia coli and Staphylococcus aureus. They also have good bactericidal stability, do not produce toxic substances, and can be widely used in households. They can also be used for large-scale production in the field of purification.

[0141] One embodiment of this application provides a purification device including the above-mentioned bactericide.

[0142] It is understandable that purification devices include, but are not limited to, air purifiers, air conditioners, etc.

[0143] The present application will be described in further detail below with reference to specific embodiments, but the embodiments of the present application are not limited thereto.

[0144] The structures of the compounds (III-1) to (III-12) prepared in each example are as follows:

[0145]

[0146] Example 1

[0147] (1) The (R)-2-amino-3-(1H-indol-3-yl)propionate salt (1 eq.), NaOH (1.2 eq.), and a mixed solvent (10 mL) of dioxane and water in a volume ratio of (5:1) were used to carry out the 2-amino reaction. The reaction was carried out at room temperature for 24 hours, and the reaction was monitored by TLC. After the reaction was completed, the solution was evaporated under reduced pressure, extracted three times with DCM and water, the organic phase was dried, and then separated by column chromatography to obtain (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propionate salt;

[0148] (2) The (R)-2-((tert-butoxycarbonyl)amino)-3-(1H-indole-3-yl)propionate obtained in step (1) was dissolved in DMSO (20 mL) and stirred at 0 °C for 5 minutes. Then, 1-bromo-3-methylbutene (10.0 eq.) and KOH (3.0 eq.) were added, and the reaction was carried out at room temperature for 2 hours. The reaction was monitored by TLC. After the reaction was completed, NH4Cl was added to quench the reaction, the mixture was evaporated under reduced pressure, extracted three times with DCM and water, the organic phase was dried, and the N-dimethylpropenyl-substituted indole intermediate was obtained by column chromatography.

[0149] (3) The N-dimethylpropenyl-substituted indole intermediate obtained in step (2) was dissolved in DCM, and TFA (3.0 eq.) was added to remove Boc. The reaction was monitored by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted three times with DCM and water, the organic phase was dried, and then column chromatography was performed to obtain the compound shown in formula (IV-1).

[0150] (4) Add (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) to a DCM solution (50 mL) containing HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.), then add dropwise a DCM solution of the compound of formula (IV-1) obtained in step (3). React at room temperature for 8 hours, and monitor the reaction by TLC. After the reaction is complete, evaporate to dryness under reduced pressure, extract three times with DCM and water, dry the organic phase, and then separate the product by column chromatography. The product was identified as the compound of formula (III-1), and the proton NMR spectrum is shown below. Figure 1 As shown.

[0151] Example 2

[0152] (1) Dissolve (S)-2-((tert-butoxycarbonyl)amino)-3-(1H-indole-3-yl)propionic acid in DMSO and stir at 0 °C for 5 minutes. Then add MeI (10.0 eq.) and KOH (3.0 eq.) and react at room temperature for 2 hours, and monitor the reaction by TLC. After the reaction is complete, add NH4Cl to quench the reaction, evaporate to dryness under reduced pressure, extract three times with DCM and water, dry the organic phase, and separate by column chromatography to obtain N-dimethylpropenyl-substituted indole intermediate;

[0153] (2) The N-methyl-substituted indole intermediate obtained in step (1) was dissolved in DCM, and TFA (3.0 eq.) was added to remove Boc. The reaction was monitored by TLC. After the reaction was complete, the mixture was dried under reduced pressure, extracted three times with DCM and water, the organic phase was dried, and then column chromatography was performed to obtain the compound shown in formula (IV-2).

[0154] (3) Add (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) to a DCM solution (50 mL) containing HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.), then add dropwise a DCM solution of the compound of formula (IV-2) obtained in step (2). React at room temperature for 8 hours, and monitor the reaction by TLC. After the reaction is complete, evaporate to dryness under reduced pressure, extract three times with DCM and water, dry the organic phase, and then separate the product by column chromatography. The product was identified as the compound of formula (III-2), and its proton NMR spectrum is shown below. Figure 2 As shown.

[0155] Example 3

[0156] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a DCM solution of L-tyrosine hydrochloride was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the mixture was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-3). The 1H NMR spectrum is shown below. Figure 3 As shown.

[0157] Example 4

[0158] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a DCM solution of (S)-2-amino-3-phenylpropionate was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the mixture was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-4). The proton NMR spectrum is shown below. Figure 4 As shown.

[0159] Example 5

[0160] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a solution of (S)-2-amino-3-(4-(benzyloxy)phenyl)propionate in DCM was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the solution was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-5). The proton NMR spectrum is shown below. Figure 5 As shown.

[0161] Example 6

[0162] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a solution of (R)-2-amino-3-(4-chlorophenyl)propionate in DCM was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the solution was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-6). The proton NMR spectrum is shown below. Figure 6 As shown.

[0163] Example 7

[0164] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a DCM solution of 4-nitro-L-phenylalanine hydrochloride was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the mixture was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-7). The 1H NMR spectrum is shown below. Figure 7 As shown.

[0165] Example 8

[0166] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a DCM solution of (S)-2-aminopropionate was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the mixture was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-8). The proton NMR spectrum is shown below. Figure 8 As shown.

[0167] Example 9

[0168] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a DCM solution of DL-threonine hydrochloride was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the mixture was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-9). The 1H NMR spectrum is shown below. Figure 9 As shown.

[0169] Example 10

[0170] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a DCM solution of 1-aminocyclobutanecarboxylic acid was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the mixture was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-10). The 1H NMR spectrum is shown below. Figure 10 As shown.

[0171] Example 11

[0172] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a DCM solution of L-glutamic acid dicarboxylate was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, monitored by TLC. After the reaction was complete, the mixture was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-11). The 1H NMR spectrum is shown below. Figure 11 As shown.

[0173] Example 12

[0174] (R)-3-phenyl-2-hydroxypropionic acid (1.0 eq.) was added to a solution of HOBt (1.0 eq.), EDCI (1.0 eq.), and DIPEA (1.0 eq.) in DCM (50 mL). Then, a solution of (S)-2-amino-3-cyclohexylpropionate in DCM was added dropwise to the above solution. The reaction was carried out at room temperature for 8 hours, and the reaction was monitored by TLC. After the reaction was complete, the mixture was evaporated to dryness under reduced pressure, extracted three times with DCM and water, and the organic phase was dried. The product was then separated by column chromatography and identified as the compound of formula (III-12). The proton NMR spectrum is shown below. Figure 12 As shown.

[0175] The organic compounds prepared in each embodiment were subjected to bactericidal tests. The test method was as follows: 1 mg of the final product was dissolved in 0.6 mL of chromatographic methanol to verify that the purity of the compounds shown in formulas (III-1) to (III-12) reached 99.99%. Then, 1 mg of the final product was dissolved in 1 mL of DMSO to obtain an organic compound solution. After spraying the organic compound solution into a petri dish, the survival rate of Escherichia coli and Staphylococcus aureus was observed at different times (5 min, 6 h, 24 h). The results are shown in Table 1.

[0176] Table 1

[0177]

[0178] As can be seen from Table 1, the compounds prepared in each example have good bactericidal effects.

[0179] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0180] The embodiments described above are merely illustrative of several implementation methods of this application, intended to facilitate a detailed understanding of the technical solutions of this application, but should not be construed as limiting the scope of protection of the invention patent. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of this application, and these all fall within the scope of protection of this application. It should be understood that technical solutions obtained by those skilled in the art based on the technical solutions provided in this application through logical analysis, reasoning, or limited experimentation are all within the scope of protection of the appended claims. Therefore, the scope of protection of this patent application should be determined by the content of the appended claims, and the specification can be used to interpret the content of the claims.

Claims

1. An organic compound, characterized in that, It has the general formula shown in equation (I): Wherein, L is selected from at least one of single bond and ethylene; R1 is hydrogen, and R2 is selected from hydrogen or one of the structures of formulas (II-1) to (II-10): Alternatively, R1, R2, and the C atoms connected to them together form a cyclobutyl group.

2. The organic compound according to claim 1, characterized in that, The organic compound is selected from one of the structures of formulas (III-1) to (III-12): 。 3. A method for preparing an organic compound, characterized in that, Includes the following steps: A condensation reaction was carried out by mixing (R)-3-phenyl-2-hydroxypropionic acid and the compound shown in formula (IV) to produce the compound of formula (I): In equations (I) and (IV), L is selected from at least one of single bonds and ethylene; R1 is hydrogen, and R2 is selected from hydrogen or one of the structures of formulas (II-1) to (II-10): Alternatively, R1, R2, and the C atoms connected to them together form a cyclobutyl group.

4. The method for preparing the organic compound according to claim 3, characterized in that, The compound shown in formula (IV) includes at least one of the structures of formulas (IV-1) to (IV-12): 。 5. The method for preparing the organic compound according to any one of claims 3 to 4, characterized in that, The condensation reaction is carried out in the presence of a catalyst selected from at least one of HOBT, EDCI, and DIPEA; and / or The solvent for the condensation reaction is DCM.

6. The use of the organic compound as described in any one of claims 1 to 2 or the organic compound prepared by the preparation method as described in any one of claims 3 to 5 in the preparation of bactericides.

7. A bactericide, characterized in that, This includes organic compounds as described in any one of claims 1 to 2 or organic compounds prepared by the preparation method described in any one of claims 3 to 5.

8. A purification device, characterized in that, Includes the bactericide as described in claim 7.

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