CN107089975A - Thiazole salt compounds containing 1,3,4 oxadiazolyls and preparation method and application - Google Patents
Thiazole salt compounds containing 1,3,4 oxadiazolyls and preparation method and application Download PDFInfo
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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Abstract
The invention discloses a kind of thiazole salt compounds containing 1,3,4 oxadiazolyls and preparation method and application, the compound has as led to the structure shown in formula (I)：
Description
Technical field
The present invention relates to field of pharmaceutical chemistry technology, especially a kind of thiazole salt compounds for containing 1,3,4- oxadiazolyls
And preparation method and application.
Background technology
In recent years, with the continuous change of ecological condition, kind and cropping system, (such as paddy rice is white for bacterial diseases of plants
Leaf blight, tobacco bacterial wilt and citrus bacterial canker disease etc.) occur on a large scale and popular in China, and have in the whole nation further spread it is climing
Prolong trend, the scope that causes harm is wide, preventing and treating is difficult, existing commercial antimicrobial agent (such as Yekuzuo, Thiodiazole-copper, can kill must) preventive effect
Low, resistance, is badly in need of finding the efficiently anti-reactive compound for planting sick bacterium, the green of independent intellectual property right is formulated out on this basis
Color novel pesticide, drug candidate is provided for crops are bacillary with Disease prevention and control.
And the derivative containing thiazole salt shows the bioactivity of wide spectrum, there is resisting gram-positive such as in terms of sterilization
The bioactivity such as (or negative) bacterium, the focus paid close attention to as region of chemistry and biological educational circles scholars.With traditional quaternary ammonium salt sun from
Son is compared, the features such as there is thiazole salt cation good flatness, electronics easily to shift, delocalization is good, is easily sent out with acceptor
Raw effect, and its synthesis is simple, with low cost, can upset the defense mechanism that microbial cell film originally has, therefore with extensive
Bioactivity.Meanwhile, the compound containing 1,3,4- oxadiazole group is synthesized and studied extensively, has reported this kind of compound tool
There is the bioactivity (such as sterilization, desinsection, weeding, anti-inflammatory) of wide spectrum.
, will based on the present invention is with the derivative containing 1,3,4- oxadiazole group in order to find and find efficient germicide
The thiazole salt groups that target compound bioactivity can be improved are incorporated into this system, and synthesis is a series of to contain 1,3,4- oxadiazoles
The thiazole salt compounds of group, test its anti-sick bacterial activity of plant, research and development and initiative for novel pesticide provide scientific basic.
1,3,4- oxadiazole class compound progress with bioactivity：
, Xu [Xu, W.M. in 2011；Yang,S.；Bhadury,P.；He,J.；He,M.；Gao,L.L.；Hu,D.Y.；
Song,B.A.Synthesis and bioactivity of novel sulfone derivatives containing 2,
4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase
Inhibitors.Pestic.Biochem.Physiol., 2011,11,6-15] synthesize the sulphur of the group of oxadiazole containing 1,3,4-
Ether or sulfone derivatives are as chitinase inhibitors, and biological activity test result shows, such compound has good resist
Fungi activity.Wherein, compound 17a, 17b, 17c are distinguished the inhibiting rate of fusarium graminearum under 50 μ g/mL concentration
85.1%, 100.0%, 79.9%, be above comparison medicament hymexazol inhibiting rate (60.7%), it is further test result indicates that
Compound 15b can be used for the prevention and control of plant fungal disease as chitinase inhibitors.
, [Li, the P. such as Li in 2013；Yin,J.；Xu,W.M.；Wu,J.；He,M.；Hu,D.Y.；Yang,S.；Song,
B.A.Synthesis,antibacterial activities,and 3D-QSAR of sulfone derivatives
containing 1,3,4-oxadiazole moiety.Chem.Biol.Drug.Des.；2013；82,546-556] one is synthesized
Series contains the sulfone compound of 1,3,4- oxadiazole groups, and bacteriostatic activity test result shows that such compound is to tomato and cigarette
Careless ralstonia solanacearum shows preferable inhibitory activity.Wherein, compound 22a and 22b is shown to tomato and tobacco ralstonia solanacearum
Best inhibitory activity, EC50Respectively 19.77 and 8.29 μ g/mL, better than comparison medicament can kill 3000 and thiophene bacterium ketone (both
To the EC of bacterial wilt of tomato bacterium50Respectively 93.59 and 99.80 μ g/mL, to the EC of tobacco ralstonia solanacearum50Respectively 45.91 Hes
216.70μg/mL)。
, [Wang, the P.Y. such as Wang in 2016；Zhou,L.；Zhou,J.；Wu,Z.B.；Xue,W.；Song,B.A.；
Yang,S.Synthesis and antibacterial activity of pyridinium-tailored 2,5-
substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone
Derivatives.Bioorg.Med.Chem.Lett., 2016,26,1214-1217] designed and synthesized it is a series of contain pyridine
The 1 of salt, 3,4- oxadiazole thioethers/sulfoxide/sulfone compound, and bacteriostatic activity test, bioactivity are carried out to such compound
Test result shows that the series compound has good inhibiting effect, wherein compound 26a, 26b to phytopathogenic bacteria,
26c, 246,26e, 26f, 26g show significant suppression to rice leaf spot bacteria, tobacco ralstonia solanacearum, citrus processing
Activity, its EC50The scope of value is 0.54~12.14 μ g/mL, far above comparison medicament Yekuzuo to rice leaf spot bacteria
EC50(92.61 μ g/mL) and thiophene bacterium ketone are to tobacco ralstonia solanacearum and the EC of citrus processing50(be respectively 216.7 μ g/mL and
77.04μg/mL)。
, [Shi, the Y.J. such as Shi in 2016；Li,Y.；Fang,Y.；Chen,J.；Ye,L.Y.；Ge,S.S.；Dai,
H.Synthesis and biological activities of novel cyanoacrylates containing 1,3,
4-oxadiazole moiety.Chin.J.Org.Chem., 2016,36,2472-2478] pass through active substructure splicing side
Method, has synthesized a series of cyanoacrylate compounds for containing 1,3,4- oxadiazole rings, preliminary biological activity test result
Show that such compound has certain activity of weeding, under 1500g/ha dosage, compound 28a presses down to the cauline leaf process of chickweed
Rate processed is 80%, and compound 28b is 70% to the cauline leaf process inhibiting rate of small lamb's-quarters.
Thiazole salt compounds progress with broad-spectrum biological activity：
, [Maeda, the T. such as Maeda in 1999；Yoshida,M.；Okazaki,K.；Nagamune,H.；Kourai,
H.Synthesis and Antimicrobial Characteristics of 5,5'-[2,2'-
(Tetramethylenedicarbonyldioxy)diethyl]bis(3-alkyl-4-methylthiazolium
Iodide) .Biocontrol.Sci.Lett., 1999,4,75-81] synthesize the symmetrical T-n dimerization of one group of different alkyl chain length
Thiazole salt-gemini quaternary ammonium salt of body.Biological activity determination result shows, compound 30 has wide spectrum, efficient bactericidal and true
Bacterium activity, when a length of 12 carbon of chain, activity preferably, and effect be superior to commercially available medicine dodecyl benzyl dimethyl ammonium chloride and
Probenazole.
, [Zablotskaya, the A. such as Zablotskaya in 2015；Segal,I.；Geronikaki,A.；
Kazachonokh,G.；Popelis,Y.；Shestakova,I.Synthesis and biological evaluation of
lipid-like 5-(2-hydroxyethyl)-4-methyl-1,3-thiazole derivatives as potential
Anticancer and antimicrobial agents.Med.Chem.Commun., 2015,6,1464-1470] synthesis
The thiazole salt compounds of difference substitution, and its antitumor and antibacterial activity is tested in vitro.Biological activity test result shows,
Wherein compound 33a and 33b shows very strong antibacterial activity to Gram- (+), wherein, to the minimum of staphylococcus aureus
Inhibition concentration<2 μ g/mL, minimum bactericidal concentration is 4 μ g/mL.Structure-activity relationship shows that the activity of this kind of compound depends on alkyl
Length, the position of alkylation, the quantity of alkyl of chain.
, [Tejero, the R. such as Tejero in 2015；López,D.；López-Fabal,F.；Gómez-Garcés,J.；
Fernández-García,M.High Efficiency Antimicrobial Thiazolium and Triazolium
Side-Chain Polymethacrylates Obtained by Controlled Alkylation of the
Corresponding Azole Derivatives.biomacromolecules, 2015,16,1844-1854] synthesize 2 kinds
Polymer 34a and 34b, and study its influence of quaterisation degree (DQs) to antibacterial activity.Active testing shows, in season
When ammonium reaches 100%, both show obvious antibacterial activity, and its MIC value is respectively 8 μ g/mL and 4 μ g/mL.
The content of the invention
The purpose of the present invention is：There is provided a kind of thiazole salt compounds of the oxadiazolyl containing 1,3,4- and preparation method thereof and
Using it has good inhibition, and its synthetic method economical and convenient to infective pathogen bacterium.
What the present invention was realized in：One kind contains the thiazole salt compounds of 1,3,4- oxadiazolyls, and the compound has
Structure as shown in formula (I)：
In formula, substituent on phenyl ring is more than one, R1For hydrogen, C1-4Alkyl, trifluoromethyl, C1-3Alkoxy, trifluoro
Methoxyl group, hydroxyl, acrylic, acrylamido, amino, C1-3Alkylamino, nitro or halogen atom；R2For hydrogen, C1-4Alkyl, three
Methyl fluoride, C1-3Alkoxy, nitro or halogen atom；X is oxygen atom or sulphur atom；n1For 0,1,2 or 3；n2For the nature more than 1
Number.
The preparation method of thiazole salt compounds containing 1,3,4- oxadiazolyl, it is characterised in that：Its synthetic route is as follows；
In formula, R1For hydrogen, C1-4Alkyl, trifluoromethyl, C1-3Alkoxy, trifluoromethoxy, hydroxyl, acrylic, acryloyl
Amido, amino, C1-3Alkylamino, nitro or halogen atom；R2For hydrogen, C1-4Alkyl, trifluoromethyl, C1-3Alkoxy, nitro or halogen
Plain atom；X is oxygen atom or sulphur atom；n1For 0,1,2 or 3；n2For the natural number more than 1.
Application of the thiazole salt compounds of the oxadiazolyl containing 1,3,4- in the medicine for preparing anti-infective pathogen bacterium.
By using above-mentioned technical proposal, based on the present invention is with the derivative containing 1,3,4- oxadiazole group, it is possible to
The thiazole salt cation for improving target compound bioactivity is incorporated into this system, and synthesis is a series of to contain 1,3,4- oxadiazolyls
Thiazole salt compounds, by the biological activity test to phytopathogenic bacteria, find plant of such compound to measure
There is infective pathogen bacterium (such as rice leaf spot bacteria, tobacco ralstonia solanacearum and citrus processing) good suppression to make
With providing certain science reference to research and develop and formulating novel pesticide.
Embodiment
Embodiments of the invention 1：Target compound 6- (5- (2,4 dichloro benzene base)-own thioether group) -1,3,4- oxadiazoles -
The preparation of 3- thiazole bromide salt
In 25mL round-bottomed flasks add 0.68g (1.66mmol) 2- (the own thioether group of 6- bromines) -5- (2,4 dichloro benzene base) -
1,3,4- oxadiazole, and dissolved with 5mL acetonitriles, 710 μ L thiazole liquid are subsequently added into, are heated to reflux, reaction 36h or so, TLC inspections
Survey reaction raw materials fundamental reaction completely, stop reaction, vacuum distillation removes solvent acetonitrile, add a small amount of absolute methanol dissolving, silicon
Glue mixes sample, column chromatography (dichloromethane:Absolute methanol=6:1, V/V) target product 0.62g is isolated and purified to obtain, yield 75.9%,
Fusing point：118~120 DEG C.
The synthesis of other target compounds is with reference to embodiment 1.
Structure and proton nmr spectra and the carbon spectrum of the thiazole salt compounds of part oxadiazolyl containing 1,3,4- of synthesis
As shown in table 1, physico-chemical property is as shown in table 2 for data.
The proton nmr spectra and carbon modal data of the part of compounds of table 1
The physicochemical property of the partial target compound of table 2
Pharmacological Examples 1：
EC50(median effective concentration) is the weight for assessing phytopathogen to compound responsive
Index is wanted, while being also the important parameter that compound concentration is set when studying the mechanism of action of compound.It is real in concentration gradient
In testing, suitable 5 concentration, inhibiting rate, drug concentration finally by medicament to phytopathogen are set using doubling dilution
Logarithm value is converted into, virulence curve is obtained by SPSS software regression analyses, EC is calculated50。
Using median effective concentration EC of the nephelometry test target compound to phytopathogen50, subjects are that paddy rice is white
Leaf spoting bacteria, tobacco ralstonia solanacearum and citrus processing.DMSO is dissolved in the medium as blank control.By the white leaf of paddy rice
Rot bacterium (bacterial blight of rice opportunistic pathogen is in M210 solid mediums) is put into NB culture mediums, in 28 DEG C, 180rpm constant-temperature tables
Middle shaken cultivation is standby to exponential phase；Tobacco bacterial wilt opportunistic pathogen carries out line culture on NA solid mediums, is placed on
In 30 DEG C of constant incubators, until growing single bacterium colony, tobacco ralstonia solanacearum is put into NB fluid nutrient mediums by picking single bacterium colony,
30 DEG C, shaken cultivation is standby to exponential phase in 180rpm constant-temperature tables；By citrus processing (in M210 solid mediums
On) be put into NB culture mediums, shaken cultivation is standby to exponential phase in 28 DEG C, 180rpm constant-temperature tables.By medicament (chemical combination
Thing) it is configured to various concentrations (example：80,40,20,10,5 μ g/mL) toxic NB fluid nutrient mediums 5mL be added in test tube, point
40 μ L are not added and contain the NB fluid nutrient mediums for planting sick bacterium, are vibrated in 28-30 DEG C, 180rpm constant-temperature tables, and its paddy rice is white
Leaf blight opportunistic pathogen culture 48h, tobacco ralstonia solanacearum culture 24h, citrus processing culture 36h.The bacterium solution of each concentration is existed
OD is determined on spectrophotometer595Value, and the OD of the toxic sterile NB fluid nutrient mediums of corresponding concentration is determined in addition595Value.
Correct the OD values=values of OD containing bacterium culture medium-aseptic culture medium OD values
Inhibiting rate %=[(control medium bacterium solution OD values after correction-correct toxic culture medium OD values)/compareed after correcting
Culture medium bacterium solution OD values] × 100
The embodiment of the present invention is aided with explanation technical scheme, but the content of embodiment is not limited thereto, part
Target compound experimental result is as shown in table 3.
Inhibitory activity of the thiazole salt compounds of the oxadiazolyl containing 1,3,4- of table 3 to plant pathogenetic bacteria
" NT " represents not test
From table 3 it is observed that in vitro in biological activity test, target compound is to plant pathogenic pathogen (such as water
Rice bacterial leaf spot pathogenic bacteria, tobacco ralstonia solanacearum and citrus processing) show preferable inhibitory activity.It is worth mentioning
It is that target compound shows the inhibitory activity of relative good to rice leaf spot bacteria, its EC50In 0.10~10.56 μ g/mL
In the range of, wherein, the inhibitory activity of compound 47 is best, its EC50For 0.10 μ g/mL.Compound is to citrus processing also table
Reveal preferable inhibitory activity, its EC50In the range of 2.34~17.58 μ g/mL, wherein, the inhibition of compound 13 is optimal,
Its EC50For 2.34 μ g/mL.And for the EC of tobacco ralstonia solanacearum inhibitory activity50It is worth in the range of 3.27~85.27 μ g/mL,
Wherein, the best compound of activity is 30, its EC50For 3.27 μ g/mL.For the overall inhibition that 3 kinds are planted with sick bacterium, mesh
3 kinds of mark compound 12,16,30,32,36,40,46,47 and 48 pair plants sick bacterium and shows wide spectrum inhibition, its EC50
Between 0.10~14.59 μ g/mL.It can be seen that, compound of the invention can as anti-plant pathogenetic bacteria candidate's agricultural chemicals.
Claims (3)
1. one kind contains the thiazole salt compounds of 1,3,4- oxadiazolyls, it is characterised in that：The compound has such as formula (I) institute
The structure shown：
In formula, R1For hydrogen, C1-4Alkyl, trifluoromethyl, C1-3Alkoxy, trifluoromethoxy, hydroxyl, acrylic, acrylamido,
Amino, C1-3Alkylamino, nitro or halogen atom；R2For hydrogen, C1-4Alkyl, trifluoromethyl, C1-3Alkoxy, nitro or halogen are former
Son；X is oxygen atom or sulphur atom；n1For 0,1,2 or 3；n2For the natural number more than 1.
2. a kind of preparation method of the thiazole salt compounds as claimed in claim 1 containing 1,3,4- oxadiazolyls, its feature
It is：Its synthetic route is as follows：
In formula, R1For hydrogen, C1-4Alkyl, trifluoromethyl, C1-3Alkoxy, trifluoromethoxy, hydroxyl, acrylic, acrylamido,
Amino, C1-3Alkylamino, nitro or halogen atom；R2For hydrogen, C1-4Alkyl, trifluoromethyl, C1-3Alkoxy, nitro or halogen are former
Son；X is oxygen atom or sulphur atom；n1For 0,1,2 or 3；n2For the natural number more than 1.
3. the thiazole salt compounds of the oxadiazolyl as claimed in claim 1 containing 1,3,4- are preparing anti-infective pathogen bacterium
The application of medicine.
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| CN110294749A (en) * | 2019-06-12 | 2019-10-01 | 华南农业大学 | One kind (S) -1,3- thiazole benzofurane bamic acid esters compound and its preparation method and application |
| CN113636984A (en) * | 2021-08-18 | 2021-11-12 | 贵州大学 | Morpholine group-containing 1,3, 4-oxadiazole compounds and preparation method and application thereof |
| CN113979964A (en) * | 2021-11-29 | 2022-01-28 | 贵州大学 | Preparation and application of phenylalanine derivatives containing 1,3, 4-oxadiazole thioether |
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| CN110294749A (en) * | 2019-06-12 | 2019-10-01 | 华南农业大学 | One kind (S) -1,3- thiazole benzofurane bamic acid esters compound and its preparation method and application |
| CN110294749B (en) * | 2019-06-12 | 2022-01-25 | 华南农业大学 | (S) -1, 3-thiazole phenyl furan thiocarbamate compound and preparation method and application thereof |
| CN113636984A (en) * | 2021-08-18 | 2021-11-12 | 贵州大学 | Morpholine group-containing 1,3, 4-oxadiazole compounds and preparation method and application thereof |
| CN113636984B (en) * | 2021-08-18 | 2023-11-17 | 贵州大学 | Morpholine group-containing 1,3, 4-oxadiazole compound and preparation method and application thereof |
| CN113979964A (en) * | 2021-11-29 | 2022-01-28 | 贵州大学 | Preparation and application of phenylalanine derivatives containing 1,3, 4-oxadiazole thioether |
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