CN116425698B - Methylthiazole compound and preparation method and application thereof - Google Patents

Methylthiazole compound and preparation method and application thereof Download PDF

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CN116425698B
CN116425698B CN202310705970.0A CN202310705970A CN116425698B CN 116425698 B CN116425698 B CN 116425698B CN 202310705970 A CN202310705970 A CN 202310705970A CN 116425698 B CN116425698 B CN 116425698B
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methylthiazole
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CN116425698A (en
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杨平
李彩玲
谢小保
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Institute of Microbiology of Guangdong Academy of Sciences
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Abstract

The invention discloses a methylthiazole compound and a preparation method and application thereof. The structural formula of the methylthiazole compound is shown as a formula (III). The invention designs and synthesizes a series of methylthiazole compounds with brand new structures by introducing hydrophilic aminoguanidine at the C2 position and lipophilic side chains at the C4 position of a thiazole ring, and the preparation method comprises the following steps: taking 1- (4-acetylphenyl) thiourea and 2-chloro-1-substituent propan-1-one (I) as raw materials, and carrying out Hantzsch thiazole synthesis reaction to obtain a first-step product (II), wherein the first-step product (II) reacts with aminoguanidine hydrochloride to obtain a final product (III). The methylthiazole compound has antibacterial activity, especially has good antibacterial activity on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa, and can be used as an antibacterial candidate compound.

Description

Methylthiazole compound and preparation method and application thereof
Technical Field
The invention belongs to the technical field of antibiosis, relates to an antibacterial drug or an industrial bactericide, and in particular relates to a methylthiazole compound with a novel structure, and a preparation method and application thereof.
Background
Bacterial infection is a common disease and is also a common source of deterioration of materials or products in industry. Severely threatens human health and industrial production. Although several classes of bactericides or agents are currently available both pharmaceutically and industrially, the self-survival ability of microorganisms has prompted some resistance to these agents with a long history of their use. The discovery of new targets and bactericides of new structures has become an important topic of research in this area. The 2-methyl-4-isothiazolin-3-ketone (MIT) is a broad-spectrum and high-efficiency bactericide widely used in industry, and is structurally characterized in that five-membered contains nitrogen and sulfur heteroatoms and has ketone groups on the ring, and a methylthiazole compound with a brand new structure is constructed through isomerism treatment and derivative, so that the bactericide with the brand new structure is likely to be generated.
Disclosure of Invention
The first object of the invention is to provide a methylthiazole compound or a salt thereof which has a novel structure and obvious antibacterial activity on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa.
The structural formula of the methylthiazole compound is shown as a formula (III):
wherein R is selected from->、/>、/>Or->。
Preferably, R is selected fromOr->。
The second purpose of the invention is to provide a preparation method of the methylthiazole compound shown in the structural formula (III), wherein 1- (4-acetylphenyl) thiourea and 2-chloro-1-substituent propan-1-one (I) are used as raw materials, a first-step product (I) is obtained through a Hantzsch thiazole synthesis reaction, the first-step product (I) reacts with aminoguanidine hydrochloride to prepare a final product (III), and the synthesis reaction formula of the methylthiazole compound is as follows:
the method comprises the steps of carrying out a first treatment on the surface of the Wherein R is selected from->、/>、/>Or->。
Preferably, R is selected fromOr->。
Further preferably, the method comprises the following steps: the first step: adding 1- (4-acetylphenyl) thiourea, 2-chloro-1-substituent propan-1-one (I) and ethanol into a reactor, heating and stirring for reaction to obtain a first-step product (II); and a second step of: adding the product (I), aminoguanidine hydrochloride, lithium chloride and ethanol in the first step into a reactor, and heating and stirring to react to obtain the methylthiazole compound shown in the structural formula (III).
The total yield of the preparation method disclosed by the invention can be 49% -72%.
Preferably, the ratio of the amounts of the substances of the 1- (4-acetylphenyl) thiourea and the 2-chloro-1-substituent propan-1-one (I) described in the first step is 1:1.2; the ratio of the amounts of the product (II) of the first step, aminoguanidine hydrochloride and lithium chloride in the second step is 1:1.3:0.4; the heating and stirring reaction is carried out at 70 ℃.
Preferably, the 2-chloro-1-substituent propan-1-one (I) is selected from 2-chloro-1- (4-fluorophenyl) propan-1-one or 2-chloro-1- (4-isobutylphenyl) propan-1-one.
The third object of the present invention is to provide an application of the methylthiazole compound having the structural formula shown in formula (III) or a salt thereof in the preparation of an antibacterial agent.
Preferably, the antibacterial agent is an anti-staphylococcus aureus, escherichia coli and/or pseudomonas aeruginosa agent.
A fourth object of the present invention is to provide an antibacterial agent comprising the methylthiazole compound having the structural formula shown in formula (III) or a salt thereof as an active ingredient.
Compared with the prior art, the invention has the following beneficial effects:
according to modern medicine design theory and organic synthesis experimental technology, 2-methyl-4-isothiazolin-3-ketone (MIT) is modified, a series of methylthiazole compounds with brand new structures are designed and synthesized, and antibacterial activity research is carried out. The research results show that: the methylthiazole compound with novel structure has remarkable antibacterial activity on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa, and has great application value in treating bacterial infection diseases or industrial microorganism harm. Some target substances have remarkable antibacterial effect on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa, are superior to a control medicament 2-methyl-4-isothiazolin-3-one (MIT), and can be used as antibacterial candidate compounds for research.
Detailed Description
The following examples are further illustrative of the invention and are not intended to be limiting thereof.
Example 1
Preparation procedure of 2- ((4- (1- (guanidinoimino) ethyl) phenyl) amino) -4-phenyl-5-methyl-thiazole (IIIa):
10 mmol of 1- (4-acetylphenyl) thiourea, 12 mmol of 2-chloro-1-phenylpropan-1-one (Ia) and 60 mL ethanol are added into a 150 mL flask, the reaction is stirred for 3 hours at 70 ℃, the reaction is completed, the filtration is carried out, filter residues are collected and air-dried to obtain a first-step product IIa, namely 2- ((4-acetyl) phenyl) amino) -4-phenyl-5-methyl-thiazole, and the yield is 80%.
Adding 2 mmol of the first-step product IIa, 2.6 mmol of aminoguanidine hydrochloride, 0.8 mmol of lithium chloride and 50 mL ethanol into a 100 mL flask, stirring and reacting for 24 hours at 70 ℃, decompressing and spin-drying after the reaction is finished, purifying by silica gel column chromatography (300-400 meshes, wherein the eluent is methanol and dichloromethane with the volume ratio of 1:5), finally obtaining a target product (IIIa),yield 80%, total yield 64%. 1 H NMR (400 MHz, DMSO-d 6 , δ): 10.97 (s, 1H, guanidine), 10.22 (s, 1H, sec amine), 7.84 (m, 5H, guanidine and 1-benzene), 7.75 (d, J = 7.5 Hz, 2H, 1-benzene), 7.53 (m, 3H,1-benzene), 7.26 (d, J = 7.5 Hz, 2H, 1-benzene), 2.39 (s, 3H, methyl), 2.32 (s, 3H, methyl)。HRMS (ESI) m/z: [M+H] + calcd for C 19 H 21 N 6 S, 365.1548; found 365.1560。
Example 2
Preparation procedure of 2- ((4- (1- (guanidinoimino) ethyl) phenyl) amino) -4- (4-methylphenyl) -5-methyl-thiazole (IIIb):
10 mmol of 1- (4-acetylphenyl) thiourea, 12 mmol of 2-chloro-1- (4-methylphenyl) propan-1-one (Ib) and 60 mL ethanol are added into a 150 mL flask, stirred and reacted for 3 hours at 70 ℃, after the reaction is finished, filtered, and the filter residue is collected and air-dried to obtain a first-step product IIb, namely 2- ((4-acetyl) phenyl) amino) -4- (4-methylphenyl) -5-methyl-thiazole, and the yield is 90%.
2 mmol of the first-step product IIb, 2.6 mmol of aminoguanidine hydrochloride, 0.8 mmol of lithium chloride and 50 mL ethanol are added into a 100 mL flask, stirred and reacted for 24 hours at 70 ℃, and after the reaction is finished, the mixture is dried by spin-drying under reduced pressure, and silica gel column chromatography (300-400 meshes, the eluent is methanol and dichloromethane in a volume ratio of 1:5) is performed, so that the target product (IIIb) is finally obtained, and the yield is 80% and the total yield is 72%. 1 H NMR (400 MHz, DMSO-d 6 , δ): 10.97 (s, 1H, guanidine), 10.22 (s, 1H, sec amine), 7.84 (s, 3H, guanidine), 7.75 (d, J = 7.5 Hz, 2H, 1-benzene), 7.59 (d, J = 7.5 Hz, 2H, 1-benzene), 7.26 (d, J = 7.5 Hz, 2H, 1-benzene), 7.15 (d, J = 7.5 Hz, 2H, 1-benzene), 2.39 (s, 3H, methyl), 2.34 (s, 3H, methyl), 2.32 (s, 3H, methyl)。HRMS (ESI) m/z: [M+H] + calcd for C 20 H 23 N 6 S, 379.1704; found 379.1724。
Example 3
Preparation procedure of 2- ((4- (1- (guanidinoimino) ethyl) phenyl) amino) -4- (4-fluorophenyl) -5-methyl-thiazole (IIIc):
10 mmol of 1- (4-acetylphenyl) thiourea, 12 mmol of 2-chloro-1- (4-fluorophenyl) propan-1-one (Ic) and 60 mL ethanol are added into a 150 mL flask, the reaction is stirred for 3 hours at 70 ℃, after the reaction is finished, the filtration is carried out, the filter residues are collected and air-dried, and the product IIc in the first step, namely 2- ((4-acetyl) phenyl) amino) -4- (4-fluorophenyl) -5-methyl-thiazole is obtained, wherein the yield is 70%.
2 mmol of the first-step product IIc, 2.6 mmol of aminoguanidine hydrochloride, 0.8 mmol of lithium chloride and 50 mL ethanol are added into a 100 mL flask, the mixture is stirred and reacted for 24 hours at 70 ℃, after the reaction is finished, the mixture is dried by spin-drying under reduced pressure, and silica gel column chromatography (300-400 meshes, the eluent is methanol and dichloromethane in a volume ratio of 1:5) is performed, so that the target product (IIIc) is finally obtained, the yield is 80%, and the total yield is 56%. 1 H NMR (400 MHz, DMSO-d 6 , δ): 10.97 (s, 1H, guanidine), 10.22 (s, 1H, sec amine), 7.84 (m, 5H, guanidine and 1-benzene), 7.75 (d, J = 7.5 Hz, 2H, 1-benzene), 7.31 (m, 4H, 1-benzene), 2.39 (s, 3H, methyl), 2.32 (s, 3H, methyl)。HRMS (ESI) m/z: [M+H] + calcd for C 19 H 20 FN 6 S, 383.1454; found 383.1466。
Example 4
Preparation procedure of 2- ((4- (1- (guanidinoimino) ethyl) phenyl) amino) -4- (4-isobutylphenyl) -5-methyl-thiazole (IIId):
10 mmol of 1- (4-acetylphenyl) thiourea, 12 mmol of 2-chloro-1- (4-isobutylphenyl) propan-1-one (Id) and 60 mL ethanol are added into a 150 mL flask, stirred and reacted for 3 hours at 70 ℃, after the reaction is finished, filtered, and the filter residue is collected and air-dried to obtain a first-step product IId, namely 2- ((4-acetyl) phenyl) amino) -4- (4-isobutylphenyl) -5-methyl-thiazole, and the yield is 70%.
2 mmol of the first-stage product IId, 2.6. 2.6 mAdding mol aminoguanidine hydrochloride, 0.8 mmol lithium chloride and 50 mL ethanol into a 100 mL flask, stirring at 70 ℃ for reaction for 24 hours, performing vacuum spin-drying after the reaction is finished, purifying by silica gel column chromatography (300-400 meshes, wherein the eluent is methanol and dichloromethane with the volume ratio of 1:5), and finally obtaining the target product (IIId), wherein the yield is 70% and the total yield is 49%. 1 H NMR (400 MHz, DMSO-d 6 , δ): 10.97 (s, 1H, guanidine), 10.22 (s, 1H, sec amine), 7.84 (s, 3H, guanidine), 7.75 (d, J = 7.5 Hz, 2H, 1-benzene), 7.64 (d, J = 7.5 Hz, 2H, 1-benzene), 7.32 (d, J = 7.5 Hz, 2H, 1-benzene), 7.26 (d, J = 7.5 Hz, 2H, 1-benzene), 2.43 (s, 2H, methylene), 2.39 (s, 3H, methyl), 2.32 (s, 3H, methyl), 1.82 (m, 1H, methine), 0.87 (s, 6H,methyl)。HRMS (ESI) m/z: [M+H] + calcd for C 23 H 29 N 6 S, 421.2174; found 421.2185。
Example 5
Antibacterial Activity test of the target Compound:
2-methyl-4-isothiazolin-3-one (MIT) is used as a control reagent, MIC of the target substance is measured by a micro dilution method, and the concentration of the target compound (methylthiazoles prepared in examples 1-4) on staphylococcus aureus is measuredStaphylococcus aureus ATCC 6538P and Escherichia coliEscherichia coli ATCC 8739), pseudomonas aeruginosaPseudomonas aeruginosaATCC 9027).
The experimental procedure of the microdilution method is as follows:
200. Mu.L of the sample to be tested (2-methyl-4-isothiazolin-3-one and the methylthiazoles prepared in examples 1 to 4) was added to column 1 of the 96-well plate at a concentration of 256. Mu.g/mL, 100. Mu.L of MH broth was added to each of columns 2 to 12, 100. Mu.L was added to column 2 of the mixture from column 1, 100. Mu.L was added to column 3 of the mixture from column 2, and so forth, and finally 100. Mu.L was added to column 11 of the mixture from column 10, and 100. Mu.L of the excess liquid was removed for discarding. 100 mu L of the mixture is taken to have the concentration of 10 6 Adding cfu/mL bacterial liquid into each well of columns 1-11, taking 100 mu L of bacterial liquid with concentration of 10 6 cfu/mL of bacterial liquid is added into four holes before the 12 th column, 100 mu L of MH broth is taken and added into four holes after the 12 th columnThe final volume of each well is 200 mu L, the concentrations of the samples to be tested in columns 1-11 are 128, 64, 32, 16, 8, 4, 2, 1, 0.5, 0.25 and 0.12 mu g/mL in sequence, four wells before column 12 are added with bacteria and are not added with medicine (positive growth control), and four wells after column 12 are added with bacteria and are not added with medicine (sterile control). Three replicates were made for each sample tested. After culturing the 96-well plate in a 37 ℃ oven for 24 hours, measuring OD by using an enzyme-labeled instrument 600 Value, OD 600 The concentration of wells with values close to the sterile control was the minimum inhibitory concentration MIC.
The results show that:
(1) MIC of 2-methyl-4-isothiazolin-3-one (MIT) on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa was 16 mug/mL, 16 mug/mL and 16 mug/mL respectively.
(2) 2- ((4- (1- (guanidyl imino) ethyl) phenyl) amino) -4-phenyl-5-methyl-thiazole (IIIa) has the MIC of 8 mug/mL, 32 mug/mL and 64 mug/mL on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa respectively, and the antibacterial effect on staphylococcus aureus is superior to that of a control medicament 2-methyl-4-isothiazolin-3-ketone (MIT).
(3) 2- ((4- (1- (guanidyl imino) ethyl) phenyl) amino) -4- (4-methylphenyl) -5-methyl-thiazole (IIIb) has the MIC of 8 mug/mL, 16 mug/mL and 64 mug/mL on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa respectively, the antibacterial effect on staphylococcus aureus is superior to that of a control medicament 2-methyl-4-isothiazolin-3-one (MIT), and the antibacterial effect on escherichia coli is equivalent to that of the control medicament 2-methyl-4-isothiazolin-3-one (MIT).
(4) The MIC of 2- ((4- (1- (guanidyl imino) ethyl) phenyl) amino) -4- (4-fluorophenyl) -5-methyl-thiazole (IIIc) on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa is 0.5 mug/mL, 0.5 mug/mL and the antibacterial effect on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa is better than that of the control medicament 2-methyl-4-isothiazolin-3-ketone (MIT).
(5) The MIC of 2- ((4- (1- (guanidyl imino) ethyl) phenyl) amino) -4- (4-isobutylphenyl) -5-methyl-thiazole (IIId) on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa is 0.5 mug/mL, 0.5 mug/mL and 1 mug/mL respectively, and the antibacterial effect on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa is better than that of the control medicament 2-methyl-4-isothiazolin-3-ketone (MIT).
The foregoing is merely a preferred embodiment of the present invention, and it should be noted that the above-mentioned preferred embodiment should not be construed as limiting the invention, and the scope of the invention should be defined by the appended claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and such modifications and adaptations are intended to be comprehended within the scope of the invention.

Claims (6)

1. The structural formula of the methylthiazole compound is shown as formula (III):
formula (III)
R is selected fromOr->。
2. The method for preparing the methylthiazole compound or the salt thereof according to claim 1, which is characterized in that 1- (4-acetylphenyl) thiourea and 2-chloro-1-substituent propan-1-one (I) are taken as raw materials, a first step of product (II) is obtained through Hantzsch thiazole synthesis reaction, the first step of product (II) reacts with aminoguanidine hydrochloride through Schiff base to prepare a final product methylthiazole compound (III), and the synthesis reaction formula of the methylthiazole compound is as follows:
wherein R is selected fromOr->。
3. The preparation method according to claim 2, characterized by comprising the steps of: the first step: adding 1- (4-acetylphenyl) thiourea, 2-chloro-1-substituent propan-1-one (I) and ethanol into a reactor, heating and stirring for reaction to obtain a first-step product (II); and a second step of: adding the product (II), aminoguanidine hydrochloride, lithium chloride and ethanol in the first step into a reactor, and heating and stirring to react to obtain the methylthiazole compound.
4. A process according to claim 3, wherein the ratio of the amounts of the substances of 1- (4-acetylphenyl) thiourea and 2-chloro-1-substituent propan-1-one (I) in the first step is 1:1.2; the ratio of the amounts of the product (II) of the first step, aminoguanidine hydrochloride and lithium chloride in the second step is 1:1.3:0.4; the heating and stirring reaction is carried out at 70 ℃.
5. The use of a methylthiazole compound or a salt thereof as claimed in claim 1 in the manufacture of an antibacterial agent against staphylococcus aureus, escherichia coli and/or pseudomonas aeruginosa.
6. An antibacterial agent comprising the methylthiazole compound of claim 1 or a salt thereof as an active ingredient, wherein the antibacterial agent is an anti-staphylococcus aureus, escherichia coli and/or pseudomonas aeruginosa agent.
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