CN104788473A - Antibacterial compound as well as preparation method and application thereof - Google Patents

Antibacterial compound as well as preparation method and application thereof Download PDF

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Publication number
CN104788473A
CN104788473A CN201510132552.2A CN201510132552A CN104788473A CN 104788473 A CN104788473 A CN 104788473A CN 201510132552 A CN201510132552 A CN 201510132552A CN 104788473 A CN104788473 A CN 104788473A
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compound
preparation
aryl
triazine
methoxyl group
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CN104788473B (en
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刘斯婕
何敬宇
张宝华
贾鹏飞
史兰香
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Shijiazhuang University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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 application of a 3-aryl-6-aryl-7H-thiazolo [3,2-b]-1,2,4-triazine-7-ketone derivative with a general formula I shown in the description to an antibacterial drug. In the general formula I, R1 and R2 are methyl, halogen, hydroxyl, methoxyl, acetyl, propionyl, formylphenyl, carbamoyl-methoxy-benzyl, 4-methylanilino formyl-methoxyl or chloroaniline formyl-methoxyl respectively and independently. The 3-aryl-6-aryl-7H-thiazolo [3,2-b]-1,2,4-triazine-7-ketone derivative, namely an antibacterial compound provided by the invention, has obvious inhibiting effects on methicillin-resistant staphylococcus aureus, escherichia coli, pseudomonas aeruginosa and a variety of bacteria, and can be used for the preparation of the antibacterial drug.

Description

A kind of compound with antibacterial ability and preparation method thereof and purposes
Technical field
The present invention relates to chemical pharmaceutical technical field, particularly relate to 3-aryl-6-aryl-7H-thiazole also [3,2-b]-1,2,4-triazine-7-ketones derivant and they preparation antibacterials in application.
Background technology
Since the forties in 20th century penicillin be applied to clinical since, the life of countless people saved by microbiotic, therefore penicillin also become one of greatest discovery of 20th century mankind, and started new era of microbiotic research, cynnematin, quinolones, Macrolide are emerged in large numbers, polytype microbiotic such as aminoglycoside.Really we have the so various antimicrobial drug of kind, but along with antibiotic abuse, the resistance problems of bacterium also becomes increasingly conspicuous.In fact, nearly all microbiotic has all met with the challenge of corresponding Resistant strain.Since New Grinea in 1967 finds to have penicillin the streptococcus pneumoniae of resistance, have been found that multiple drug-resistant bacteria clinically, comprise methicillin-resistant staphylococcus aureus, extended spectrumβ-lactamase producing strains, vancomycin-resistant enterococcus, AmpC enzyme and metallo-β-lactamase producing strains and several drug resistance tubercule bacillus etc.The particularly discovery of superbacteria NDM-1 in 2010, allows drug-resistant bacteria cause shock and the fear of global range again.The appearance of these Resistant strain makes the application of the effective clinical of existing antibacterials occur crisis.Therefore, in order to ensure still having operational effective antibacterials from now on, particularly for the active drug of Resistant strain, exploration has novel, and active higher antibacterials are significant.
Summary of the invention
The object of the present invention is to provide a kind of 3-aryl-6-aryl-7H-thiazole also [3,2-b]-1,2,4-triazine-7-ketones derivant, the especially application of this compound in preparation antibacterials.
Above-mentioned purpose of the present invention is achieved by the following technical solution:
A kind of compound with antibacterial ability, this compound is 3-aryl-6-aryl-7H-thiazole also [3, the 2-b]-1,2 with general formula I, 4-triazine-7-ketones derivant or the acceptable hydrate of its pharmacy, salt, comprise its steric isomer or tautomer;
R in formula I 1, R 2independently be methyl, halogen, hydroxyl, methoxyl group, ethanoyl, propionyl, formylphenyl, benzamido group formyl radical methoxyl group, 4-toluidine formyl radical methoxyl group or 4-chloroanilino formyl radical methoxyl group.
As a preferred technical solution of the present invention, R 1for hydroxyl.
As a preferred technical solution of the present invention, R 2for ethanoyl.
As a preferred technical solution of the present invention, R 2for propionyl.
As a preferred technical solution of the present invention, R 2for formylphenyl.
As a preferred technical solution of the present invention, R 2for benzamido group formyl radical methoxyl group.
Present invention also offers the purposes of above-claimed cpd for the preparation of antibacterials.
" pharmacy acceptable salt " refers to the biopotency and the character that remain type I compound, and with the acid of suitable non-toxic organic or inorganic or the conventional acid addition salts that formed of organic or inorganic alkali or base addition salt.The example of acid salt comprises acetate, adipate, alginate, aspartate, benzoate, benzene sulfonate, hydrosulfate, butyrates, Citrate trianion, camphorate, camsilate, cipionate, digluconate, dodecyl sulfate, esilate, fumarate, gluceptate, glycerophosphate, Hemisulphate, enanthate, hexanoate, hydrogen chlorate, hydrobromate, hydriodate, 2-isethionate, lactic acid salt, maleate, mesylate, 2-naphthalenesulfonate, nicotinate, nitrate, oxalate, pamoate, pectinic acid salt, persulphate, 3-phenylpropionic acid salt, picrate, Pivalate, propionic salt, succinate, vitriol, tartrate, thiocyanate-, tosylate and undecylate.Alkali salt comprises ammonium salt, an alkali metal salt, such as sodium and sylvite, alkaline earth salt, such as calcium and magnesium salts, the salt of organic bases, such as dicyclohexyl amine salt, N-methyl-D-glucamine salt, and amino acid whose salt, such as arginine, Methionin etc., and, Basic nitrogen-containing groups can be quaternized with such reagent, and such as elementary alkyl halide, as methyl, ethyl, the chlorine of propyl group and butyl, bromine and iodide; Dialkyl sulfate, as methyl-sulfate, diethyl ester, dibutylester and diamyl ester; Long chain halide, as decyl, lauryl, the chlorine of myristyl and stearyl-, bromine and iodide; Aralkyl halide, as the bromide etc. of benzyl and styroyl.The acid being preferred for generating acid salt comprises hydrochloric acid and acetic acid.
Present invention also offers the preparation method of above-mentioned compound of Formula I, the method is shown in following formula.
Present invention also offers the application of above-mentioned compound of Formula I in preparation antibacterials.
Present system research and illustrate structure and the preparation of above-claimed cpd, especially ground-breakingly explores its purposes in preparation antibacterials, for development of new antibacterials provide brand-new direction and wide platform.
Embodiment
Embodiment 1
2-methyl-4-(the preparation of 4-acetoxyl group benzylidene) azolactone
By p-Hydroxybenzaldehyde 0.1 mol, acetyl glycine 0.13 mol, sodium acetate, anhydrous 0.12mol and aceticanhydride 50 g join in the three-necked bottle of 100 mL successively, temperature control 90 DEG C, stirring reaction 5 h, after being chilled to room temperature, solution becomes solid, suction filtration, filter cake cold water washing, yellow powder 24.5 g is obtained, yield 100%, ESI-MS (m/z): 246.2 after filtration cakes torrefaction.
Embodiment 2
3,4-dihydro-6-(4-hydroxybenzyl)-3-sulfo--1,2,4-triazine-5 (2 h) preparation of-one
By 2-methyl-4-(4-acetoxyl group benzylidene) azolactone (0.1mol, 24.5g), KOH (11.2g), be mixed in 500ml water, heating in water bath, make its backflow 6 hours, namely reaction solution becomes limpid, then adds thiosemicarbazide (0.12mol, 9g), mixture reaction 4.5h, reaction solution acetic acid regulates potential of hydrogen afterwards, makes its pH be 4, separate out solid, suction filtration is dry obtains yellow powder 15.7 grams, yield 66.8%, ESI-MS (m/z): 236.1 (M+H) +.
Embodiment 3
3-(4-acetylphenyl)-6-(4-hydroxybenzyl)-7 h-thiazole is [3,2-b]-1,2,4-preparation of triazine-7-ketone (L1) also
By 3,4-dihydro-6-(4-hydroxybenzyl)-3-sulfo--1,2,4-triazine-5 (2 h)-one 0.01 mol; 4-ethanoyl-alpha-chloro acetophenone 0.01 mol adds 50 mL Glacial acetic acid, after under stirring, back flow reaction 26 h, TLC monitoring reaction completes; be cooled to room temperature; reaction solution separates out solid gradually, suction filtration, after water washing; ethyl alcohol recrystallization; obtain white crystal 2.12 grams, yield 56.23%
1H-NMR (600 MHz, DMSO- d 6 ): δ 10.01 (1H, s), 7.48 (2H, d, J = 8.4Hz), 7.33 (1H, s), 7.21 (2H, d, J = 8.4Hz), 6.87 (2H, d, J = 8.4Hz), 6.80 (2H, d, J = 8.4Hz), 3.91 (2H, s), 2.76 (3H, s); ESI-MS (m/z): 378.0 (M+H) +。
Embodiment 4
3-(4-propionylphenyl)-6-(4-hydroxybenzyl)-7 h-thiazole is [3,2-b]-1,2,4-preparation of triazine-7-ketone (L2) also
By 3,4-dihydro-6-(4-hydroxybenzyl)-3-sulfo--1,2,4-triazine-5 (2 h)-one 0.01 mol; 4-propionyl-alpha-chloro acetophenone 0.01 mol adds 50 mL Glacial acetic acid; after back flow reaction 26 h, TLC monitoring reaction completes under stirring, be cooled to room temperature; reaction solution separates out solid gradually; suction filtration, after water washing, ethyl alcohol recrystallization; obtain white crystal 2.43 grams, yield 62.15%.
1H-NMR (600 MHz, DMSO- d 6 ): δ 9.98 (1H, s), 7.47 (2H, d, J = 8.4Hz), 7.32 (1H, s), 7.22 (2H, d, J = 8.4Hz), 6.89 (2H, d, J = 8.4Hz), 6.82 (2H, d, J = 8.4Hz), 3.90 (2H, s), 3.54 (2H, m), 1.18 (3H, t); ESI-MS (m/z): 392.0 (M+H) +。
Embodiment 5
3-(4-benzoylphenyl)-6-(4-hydroxybenzyl)-7 h-thiazole is [3,2-b]-1,2,4-preparation of triazine-7-ketone (L3) also
By 3,4-dihydro-6-(4-hydroxybenzyl)-3-sulfo--1,2,4-triazine-5 (2 h)-one 0.01 mol; 4-benzoyl-alpha-chloro acetophenone 0.01 mol adds 50 mL Glacial acetic acid; after back flow reaction 26 h, TLC monitoring reaction completes under stirring, be cooled to room temperature; reaction solution separates out solid gradually; suction filtration, after water washing, ethyl alcohol recrystallization; obtain white crystal 3.21 grams, yield 73.12%.
1H-NMR (600 MHz, DMSO- d 6 ): δ 9.80 (1H, s), 7.33-7.58 (7H, m), 7.30 (1H, s), 7.21 (2H, d, J = 8.4Hz), 6.87 (2H, d, J = 8.4Hz), 6.81 (2H, d, J = 8.4Hz), 3.90 (2H, s); ESI-MS (m/z): 440.2 (M+H) +。
Embodiment 6
3-(4-benzamido group formyl radical p-methoxy-phenyl)-6-(4-hydroxybenzyl)-7 h-thiazole is [3,2-b]-1,2,4-preparation of triazine-7-ketone (L4) also
By 3,4-dihydro-6-(4-hydroxybenzyl)-3-sulfo--1,2,4-triazine-5 (2 h)-one 0.01 mol; 4-benzamido group formyl radical methoxyl group-alpha-chloro acetophenone 0.01 mol adds 50 mL Glacial acetic acid; after back flow reaction 26 h, TLC monitoring reaction completes under stirring, be cooled to room temperature; reaction solution separates out solid gradually; suction filtration, after water washing, ethyl alcohol recrystallization; obtain white crystal 3.02 grams, yield 62.40%. 1H-NMR (600 MHz, DMSO- d 6 ): δ9.80 (1H, s)，8.72 (1H, t)，7.61 (2H，d， J = 8.4Hz)，7.42 (1H, s), 7.22~7.32 (5H, s), 7.21 (2H, d, J = 8.4Hz), 7.03 (2H, d, J = 9.0Hz), 6.86 (2H, d, J = 9.0Hz), , .64 (2H, s), 4.36 (2H, d), 3.89 (2H, s)；ESI-MS (m/z): 485.3。
Embodiment 7
3-[4-(4-toluidine) formyl radical p-methoxy-phenyl]-6-(4-hydroxybenzyl)-7 h-thiazole is [3,2-b]-1,2,4-preparation of triazine-7-ketone (L5) also
By 3,4-dihydro-6-(4-hydroxybenzyl)-3-sulfo--1,2,4-triazine-5 (2 h)-one 0.01 mol; 4-(4-toluidine) formyl radical methoxyl group-alpha-chloro acetophenone 0.01 mol adds 50 mL Glacial acetic acid; after back flow reaction 26 h, TLC monitoring reaction completes under stirring, be cooled to room temperature; reaction solution separates out solid gradually; suction filtration, after water washing, ethyl alcohol recrystallization; obtain white crystal 3.22 grams, yield 66.53%. 1H-NMR (600 MHz, DMSO- d 6 ): δ 10.06 (1H, s), 9.80 (1H, s)，7.61 (2H, d, J = 8.4Hz), 7.53 (2H, d, J = 8.4Hz ), 7.42 (1H, s), 7.40 (2H, d, J = 8.4Hz), 7.13 (2H, d, J = 8.4Hz), 7.05 (2H, d, J = 8.4Hz), 6.86 (2H, d, J = 8.4Hz) , 4.77 (2H, s), 3.89 (2H, s), 2.26 (3H, s); ESI-MS (m/z): 485.3 (M+H) +。
Embodiment 8
3-[4-(4-chloroanilino) formyl radical p-methoxy-phenyl]-6-(4-hydroxybenzyl)-7 h-thiazole is [3,2-b]-1,2,4-preparation of triazine-7-ketone (L6) also
By 3,4-dihydro-6-(4-hydroxybenzyl)-3-sulfo--1,2,4-triazine-5 (2 h)-one 0.01 mol; 4-(4-chloroanilino) formyl radical methoxyl group-alpha-chloro acetophenone 0.01 mol adds 50 mL Glacial acetic acid; after back flow reaction 26 h, TLC monitoring reaction completes under stirring, be cooled to room temperature; reaction solution separates out solid gradually; suction filtration, after water washing, ethyl alcohol recrystallization; obtain white crystal 3.47 grams, yield 68.85%. 1H-NMR (600 MHz, DMSO- d 6 ): δ 10.30 (1H, s), 10.01(1H, s)，7.69 (2H, d, J = 8.4Hz), 7.62 (2H, d, J = 8.4Hz ), 7.42 (1H, s), 7.40 (2H, d, J = 8.4Hz), 7.20 (2H, d, J = 8.4Hz), 7.05 (2H, d, J = 8.4Hz), 6.86 (2H, d, J = 8.4Hz) , 4.80 (2H, s), 3.90 (2H, s); ESI-MS (m/z): 505.2 (M+H) +。
Embodiment 9
Minimal inhibitory concentration (MIC) is tested
Method: testing compound is dissolved in dimethyl sulfoxide (DMSO), suitable cultured solution of broth is added in 96 hole microtiter plates, get appropriate Compound D MSO solution and be added drop-wise to 96 hole microtiter plates, to produce from 64 μ g/mL to the concentration range of 0.0625 μ g/mL, finally inoculate a certain amount of bacterium liquid (bacterial turbidity is 0.5 Maxwell), through 37 DEG C of constant temperature culture 22h, measure absorbancy, read the minimum inhibitory concentration (MIC) of compound.
Result: experiment shows, above-claimed cpd L1 of the present invention, and L2, L3, L4, L5 and L6 all have good anti-microbial activity, as shown in the table to the minimal inhibitory concentration data of different bacterium:

Claims (8)

1. one kind has the compound of antibacterial ability, it is characterized in that: this compound is 3-aryl-6-aryl-7H-thiazole also [3, the 2-b]-1,2 with general formula I, 4-triazine-7-ketones derivant or the acceptable hydrate of its pharmacy, salt, comprise its steric isomer or tautomer;
R in formula I 1, R 2independently be methyl, halogen, hydroxyl, methoxyl group, ethanoyl, propionyl, formylphenyl, benzamido group formyl radical methoxyl group, 4-toluidine formyl radical methoxyl group or 4-chloroanilino formyl radical methoxyl group.
2. the compound with antibacterial ability according to claim 1, is characterized in that: described R 1for hydroxyl.
3. the compound with antibacterial ability according to claim 1, is characterized in that: described R 2for ethanoyl.
4. the compound with antibacterial ability according to claim 1, is characterized in that: described R 2for propionyl.
5. the compound with antibacterial ability according to claim 1, is characterized in that: described R 2for formylphenyl.
6. the compound with antibacterial ability according to claim 1, is characterized in that: described R 2for benzamido group formyl radical methoxyl group.
7. the preparation method of compound according to claim 1, is characterized in that: its synthetic route is shown below.
8. compound according to claim 1 is for the preparation of the purposes of antibacterials.
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Cited By (4)

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CN105601649A (en) * 2016-03-10 2016-05-25 沈阳药科大学 Thiazolo[3,2-b]-1,2,4-triazine-3-acetic acid derivative and application thereof
CN105622637A (en) * 2016-03-10 2016-06-01 沈阳药科大学 Thiazolo[3,2-b]-1,2,4-triazine-2-carboxylic acid derivative and preparation method and application thereof
CN105884802A (en) * 2016-03-10 2016-08-24 沈阳药科大学 Thiazolo[3,2-b]-1,2,4-triazine derivative and application thereof
CN115197244A (en) * 2022-09-03 2022-10-18 石家庄学院 [1,2,4] triazino [3,2-b ] [1,3,5] thiadiazine derivative and application thereof

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CN105601649A (en) * 2016-03-10 2016-05-25 沈阳药科大学 Thiazolo[3,2-b]-1,2,4-triazine-3-acetic acid derivative and application thereof
CN105622637A (en) * 2016-03-10 2016-06-01 沈阳药科大学 Thiazolo[3,2-b]-1,2,4-triazine-2-carboxylic acid derivative and preparation method and application thereof
CN105884802A (en) * 2016-03-10 2016-08-24 沈阳药科大学 Thiazolo[3,2-b]-1,2,4-triazine derivative and application thereof
CN105884802B (en) * 2016-03-10 2017-12-15 沈阳药科大学 Thiazole simultaneously [3,2 b] 1,2,4 triazine derivatives and its application
CN115197244A (en) * 2022-09-03 2022-10-18 石家庄学院 [1,2,4] triazino [3,2-b ] [1,3,5] thiadiazine derivative and application thereof
CN115197244B (en) * 2022-09-03 2023-07-07 石家庄学院 [1,2,4] triazino [3,2-b ] [1,3,5] thiadiazine derivatives and application thereof

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