CN109516952A - A kind of pyridines hydrazone compound, synthetic method and application - Google Patents
A kind of pyridines hydrazone compound, synthetic method and application Download PDFInfo
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/88—Nicotinoylhydrazones
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Abstract
The present invention relates to a kind of pyridines hydrazone compound, synthetic method and application, the structures of compound are as follows:R is halogen.The present invention provides a kind of novel pyridines hydrazone compound of composite structure, and the hydrazone compound structure of synthesis contains pyridine ring and halogen atom, and the bioactivity of compound can be improved in N heterocycle and halogen.
Description
Technical field
The present invention relates to technical field of medical chemistry, and in particular to a kind of pyridines hydrazone compound and preparation method thereof,
And the purposes of the compound.
Background technique
As a kind of important Schiff bases compound, acylhydrazone is due to possessing a kind of special acylhydrazone group (CONHN=
CR it) causes scientists widely to pay close attention to, this group assigns hydrazone compound with preferable bioactivity, novel reason
Change property and its wide application value.
The pyridines acylhydrazone ligand of the heterocycle containing N generally has good bioactivity, stronger coordination ability and multiplicity
Coordination mode.In recent years, many document reports pyridines acylhydrazone and its superior bioactivity of complex and in other necks
The research of the extensive use in domain, such compound is paid close attention to by people.It is investigated that the synthetic method for readding existing pyridines acylhydrazone produces
Rate is low, and synthesis process is complicated.The purpose of the present invention is the novel pyridines hydrazone compounds of composite structure.
Summary of the invention
The present invention provides a kind of novel pyridines hydrazone compound of composite structure.
Technical solution of the invention:
The present invention provides a kind of pyridines hydrazone compound, it is characterised in that structure are as follows:
R is halogen.
The present invention provides a kind of pyridines hydrazone compound monocrystalline, monoclinic system, Cc space group, the length difference of crystallographic axis
ForInterplanar angle is respectively α=90.00 °,
β=93.842 (5) °, γ=90.00 °, cell volumeMolecular number Z=4 in elementary cell, unit
Electron number F (000)=600 in lattice, density Dc=1.476 gcm-3, structure are as follows:
The present invention provides a kind of pyridines hydrazone compound monocrystalline, monoclinic system, Cc space group, the length difference of crystallographic axis
ForInterplanar angle is respectively α=90.00 °, β
=93.814 (5) °, γ=90.00 °, cell volumeMolecular number Z=4 in elementary cell, unit
Electron number F (000)=672 in lattice, density Dc=1.677 gcm-3, structure are as follows:
The present invention provides a kind of pyridines hydrazone compound monocrystalline, monoclinic system, Cc space group, the length difference of crystallographic axis
ForInterplanar angle be respectively α=
90.00 °, β=93.956 (3) °, γ=90.00 °, cell volumeMolecular number Z=in elementary cell
4, electron number F (000)=744, density D in elementary cellc=1.852gcm-3, structure are as follows:
The present invention also provides a kind of synthetic methods of pyridines hydrazone compound, it is characterised in that the following steps are included:
1) 4- chloropyridine -2- formylhydrazine is synthesized:
2) 4- chloropyridine -2- formylhydrazine is dissolved in organic solvent, obtains solution 1；
3) p- halobenzene formaldehyde is dissolved in organic solvent, obtains solution 2；
4) solution 2 is added in solution 1, after a few houres of flowing back under 60 DEG C of -80 DEG C of stirrings, filtering, after filtrate stands
Generate white crystalline pyridines hydrazone compound.
Further, step 1) specifically:
It weighs after 4- chloropyridine -2- methyl formate is dissolved in organic solvent and obtains solution A, hydrazine hydrate is added into solution A,
After 65 DEG C of constant temperature stir lower water-baths reflux 4h, stop heating, after be cooled to room temperature, have crystal precipitation after standing, tied again with methanol
Crystalline substance, decompression are dried after filtering, and obtain the 4- chloropyridine -2- formylhydrazine of white；
Step 2) specifically: 4- chloropyridine -2- formylhydrazine is dissolved in methanol or ethyl alcohol, obtains solution 1.
Further, step 3) specifically: p- chlorobenzaldehyde is dissolved in glacial acetic acid, obtains solution 2；
Step 4) specifically: solution 2 is added in solution 1, after 60 DEG C are stirred lower water-bath reflux 4h, filters, filters while hot
Liquid generates the rhabdolith of a large amount of p- chlorobenzaldehyde -4- chloropyridine -2- formyl hydrazones of white after standing under room temperature one day.
Further, step 3) specifically: p- bromobenzaldehyde is dissolved in ethyl alcohol, obtains solution 2；
Step 4) specifically: solution 2 is added in solution 1, after 80 DEG C are stirred lower water-bath reflux 4h, filters, filters while hot
Liquid stands the rhabdolith for generating a large amount of p- bromobenzaldehyde -4- chloropyridine -2- formyl hydrazones of white two days later under room temperature.
Further, step 3) specifically: p- benzaldehyde iodine is dissolved in glacial acetic acid, obtains solution 2；
Step 4) specifically: solution 2 is added in solution 1, after 80 DEG C are stirred lower water-bath reflux 4h, filters, filters while hot
Liquid is stood under room temperature generates the rodlike of a large amount of p- benzaldehyde iodine benzaldehyde -4- chloropyridine -2- formyl hydrazones of white two days later
Crystal.
There are certain interactions by pyridines hydrazone compound and DNA, BSA, to Escherichia coli, Staphylococcus aureus
Bacterium, bacillus subtilis and pseudomonas aeruginosa have inhibitory effect.
Advantage for present invention:
The hydrazone compound structure of synthesis contains pyridine ring and halogen atom, and compound can be improved in N heterocycle and halogen
Bioactivity, therefore according to active principle of stacking, synthesis obtains the pyridine hydrazone compound of three kinds of halogen atom-containings.Tentatively
Bioactivity inquire into, the interaction using three kinds of compounds and ct-DNA, BSA and the inhibitory activity to 4 kinds of bacteriums carry out
Study explanation.
Detailed description of the invention
Fig. 1 is the crystal unit cell figure of chemical compounds I；
Fig. 2 is the crystal unit cell figure of compound ii；
Fig. 3 is the crystal unit cell figure of compound III；
Fig. 4 be chemical compounds I and ct-DNA effect ultraviolet spectrogram (: [DNA]/(εa-εf) and [DNA] relational graph)；
Ultraviolet spectrogram (the illustration: [DNA]/(ε of Fig. 5 compound ii and ct-DNA effecta-εf) and [DNA] relational graph)；
Ultraviolet spectrogram (the illustration: [DNA]/(ε of Fig. 6 compound III and ct-DNA effecta-εf) and [DNA] relational graph)；
Fluorescence spectra (the illustration: F of Fig. 7 chemical compounds I and BSA effect0The relational graph of/F and Q)；
Fluorescence spectra (the illustration: F of Fig. 8 compound ii and BSA effect0The relational graph of/F and Q)；
Fig. 9 is the fluorescence spectra (illustration: F of compound III and BSA effect0The relational graph of/F and Q)；
Figure 10 is the lg [(F of chemical compounds I~III0- F)/F] and lg [Q] relational graph；
The inhibitory effect of Figure 11 is concentration when being 500 μ g/mL chemical compounds I~III couple test organisms.
Specific embodiment
Embodiment 1: a kind of pyridines hydrazone compound, reaction equation and structural formula are as follows:
Structure 1 is p- chlorobenzaldehyde -4- chloropyridine -2- formyl hydrazone, molecular formula C13H9Cl2N3O, specific preparation method
Are as follows:
1) 4- chloropyridine -2- formylhydrazine is prepared；
2) 0.0686g (0.4mmol) 4- chloropyridine -2- formylhydrazine is dissolved in 10.0mL methanol, obtains solution 1；
3) it weighs 0.0562g (0.4mmol) p- chlorobenzaldehyde to be dissolved in 5mL glacial acetic acid, obtains solution after being completely dissolved
2；
4) solution 2 is slowly added in solution 1, after 60 DEG C are stirred lower water-bath reflux 4h, solution is colorless and transparent, while hot
Filtering, filtrate generate the p- chlorobenzaldehyde -4- chloropyridine -2- formyl of a large amount of white rhabdoliths after standing one day under room temperature
Hydrazone (yield 56%, 227.84~228.74 DEG C of melting range).It is p- chlorobenzaldehyde -4- chloropyridine -2- formyl hydrazone as shown in Fig. 1
Unit cell figure.
Embodiment 2: a kind of pyridines hydrazone compound, reaction equation and structural formula are as follows:
Structure II is p- bromobenzaldehyde -4- chloropyridine -2- formyl hydrazone, molecular formula C13H9BrClN3O, specific preparation side
Method are as follows:
1) 4- chloropyridine -2- formylhydrazine is prepared；
2) 0.0343g (0.2mmol) 4- chloropyridine -2- formylhydrazine is dissolved in 10.0mL ethyl alcohol, obtains solution 1；
3) it weighs 0.0370g (0.2mmol) p- bromobenzaldehyde to be dissolved in 5mL ethyl alcohol, solution 2 is obtained after being completely dissolved；
4) solution 2 is slowly added in solution 1, after 80 DEG C are stirred lower water-bath reflux 4h, solution is colorless and transparent, while hot
Filtering, filtrate stands under room temperature generates the p- bromobenzaldehyde -4- chloropyridine -2- formyl of a large amount of white rhabdoliths two days later
Hydrazone (yield 62%, 247.23-247.78 DEG C of melting range).
It is illustrated in figure 2 the crystal unit cell figure of p- bromobenzaldehyde -4- chloropyridine -2- formyl hydrazone.
Embodiment 3: a kind of pyridines hydrazone compound, reaction equation and structural formula are as follows:
Structure III is p- benzaldehyde iodine -4- chloropyridine -2- formyl hydrazone, molecular formula C13H9ClIN3O, specific preparation side
Method are as follows:
1) 4- chloropyridine -2- formylhydrazine is prepared；
2) 0.0686g (0.4mmol) 4- chloropyridine -2- formylhydrazine is dissolved in 10.0mL methanol, obtains solution 1；
3) it weighs 0.0928g (0.4mmol) p- benzaldehyde iodine to be dissolved in 5.0mL glacial acetic acid, be obtained after being completely dissolved molten
Liquid 2；
4) solution 2 is slowly added in solution 1, after 80 DEG C are stirred lower water-bath reflux 4h, solution is colorless and transparent, while hot
Filtering, filtrate generate the p- benzaldehyde iodine -4- chloropyridine -2- formyl of a large amount of white rhabdoliths after standing one day under room temperature
Hydrazone (yield 79%, 259.10~259.90 DEG C of melting range).As Fig. 3 show p- benzaldehyde iodine -4- chloropyridine -2- formyl hydrazone
Crystal unit cell figure.
Table 1 is the crystal unit cell graph parameter list of structure 1, structure II, structure III
Drug and DNA are combined with both of which: covalent bond and non-covalent bond.By noncovalent interaction, small molecule with
The combination of DNA is related to the insertion between electrostatic interaction, base-pair and the combination phase interaction of secondary and main DNA groove
With.In order to determine the Interactions Mode of acylhydrazone and ct-DNA, monitored using titration is absorbed as ct-DNA is dense
The variation of the increase absorbance of degree.
(1) preparation of Tris-HCl buffer
The trishydroxymethylaminomethane for weighing 0.3028g is dissolved with distilled water (< 250mL) and adjusts solution with dilute HCl
PH value is 7.9, is transferred to 250mL volumetric flask constant volume, matches to obtain 0.01molL-1Tris-HCl buffer.
(2) preparation of ct-DNA solution
The ct-DNA of 0.0050g is added in the Tris-HCl buffer of 40mL, it is fixed to be transferred in 50mL volumetric flask
Hold, refrigeration is stand-by.
(3) preparation of sample solution
Sample preparation 1 × 10-5mol·L-1Sample solution.It weighs after suitable sample is dissolved in the DMF of 2mL, is transferred to
In the volumetric flask of 25mL, with Tris-HCl buffer constant volume, it is stand-by to obtain sample solution.
(4) ultra-violet absorption spectrum is tested
The Tris-HCl buffer of 3.0mL is added into micro- reference cuvette, 3.0mL sample is added into article colorimetric ware
Isometric (50 μ L) 100mg almost while is respectively added with liquid-transfering gun into reference cuvette and article colorimetric ware for product solution
L-1Ct-DNA solution, be continuously added to 5 times, every minor tick 5min, make solution be uniformly mixed.Its ultra-violet absorption spectrum is measured, is swept
Retouching wave-length coverage is 250~500nm.
The binding constant K of sample and ct-DNAbBy absorbance and the utilization of collecting the dropwise addition curve under specified wavelength
EquationIt acquires, wherein εa, εfAnd εbIt respectively indicates under any ct-DNA concentration
The molar extinction coefficient of Tris-HCl buffer solution, the molar extinction coefficient of compound and compound are bonded completely with ct-DNA
Molar extinction coefficient afterwards.With Cct-DNA/(εa-εf) to Cct-DNAThe ratio of mapping, slope and intercept is compound and ct-
The binding constant K of DNAb, binding constant shows that more greatly the binding ability of compound and ct-DNA are stronger.
Embodiment 4: the p- chlorobenzaldehyde -4- chloropyridine -2- formyl hydrazone of sample I and ct-DNA are acted on, according to aforesaid operations,
As a result such as Fig. 4, the binding constant that sample I and ct-DNA can be calculated from Fig. 4 illustration is 1.45 × 104L·mol-1, say
Bright sample I and ct-DNA has stronger binding ability.
Embodiment 5: the p- bromobenzaldehyde -4- chloropyridine -2- formyl hydrazone of sample II and ct-DNA are acted on, according to above-mentioned behaviour
Make, as a result such as Fig. 5, the binding constant that compound ii and ct-DNA can be calculated from Fig. 5 illustration is 2.41 × 104L·
mol-1, illustrate that compound ii and ct-DNA have stronger binding ability.
Embodiment 6: the p- benzaldehyde iodine -4- chloropyridine -2- formyl hydrazone of sample III and ct-DNA are acted on, according to above-mentioned behaviour
Make, as a result such as Fig. 6, the binding constant that compound III and ct-DNA can be calculated from Fig. 6 illustration is 4.12 × 104L·
mol-1, illustrate that compound III and ct-DNA have stronger binding ability.
It is all that insertion is made by the mode of action of sample I, II and III and ct-DNA known to the analysis of 4,5,6 or more embodiment
With compound is partially embedded between the adjacent base pair of DNA, this Insertion action is one of drug molecule in conjunction with DNA
Important model.
7: three kinds of compounds of embodiment and bovine serum albumin interact
(1) preparation of Tris-NaCl-HCl buffer
Weigh 0.3028g trishydroxymethylaminomethane, 0.1461gNaCl is dissolved in about 250mL distilled water, stir evenly,
Make whole dissolutions, adjusts pH to 7.2 with dilute HCl, be transferred to constant volume in 250mL volumetric flask, match to obtain 0.01molL-1Tris-
NaCl-HCl buffer, for use.
(2) preparation of BSA solution
0.0033g bovine serum albumin (BSA) is weighed to be dissolved in about 50mL Tris-NaCl-HCl buffer, it is to be dissolved complete
Be transferred to constant volume in 50mL volumetric flask after complete, with 1 × 10-7mol·L-1BSA solution, refrigeration are stand-by.
(3) preparation of sample solution
Target prepares 1 × 10-5mol·L-1Sample solution.The DMF that a certain amount of sample is dissolved in 2mL is weighed, is transferred to
In the volumetric flask of 25mL, with Tris-NaCl-HCl buffer constant volume, for use.
(4) fluorescence spectrum is tested
Set measurement parameter: slit width 10nm, excitation wavelength 280nm, launch wavelength is from 300 to 540nm.?
3mLBSA solution is added in cuvette, then adds 30 μ L sample solution after 1min, is continuously added to 10 times, measures fluorescence spectrum.
Assuming that three kinds of compounds and BSA interaction are dynamic quenching, Ying Fuhe Stern-Volmer equation lg [(F0-
F)/F]=lgKA+nlg[Q].In formula, F0It is respectively the fluorescence intensity of the BSA solution system before and after compound is added with F；KqFor
Bimolecular collision quenches rate constant；τ0Fluorescence for the average life span of BSA in the presence of no quencher, large biological molecule is average
Service life is about 10-8s-1；[Q] is the concentration of compound in system；KsvFor Stern-Volmer dynamic quenching constant.With F0/ F is
Ordinate, [Q] are abscissa, and linear fit obtains respective illustration in Fig. 7,8 and 9, acquired according to the slope of fitting a straight line
KqAnd Ksv.The K of three kinds of compounds and BSA interactionqThe order of magnitude reach 1013, it is much larger than all kinds of fluorescence quenchers pair
Large biological molecule maximally diffuses collisional quenching rate constant 2.0 × 1010.It is therefore assumed that invalid.
Three kinds of compounds and BSA interaction are static quenching, and static quenching process should follow Scatchard equation: lg
[(F0- F)/F]=lgKA+nlg[Q].Wherein, F0The fluorescence for being respectively the BSA solution system before and after compound is added with F is strong
Degree；KqFor binding constant；[Q] is the concentration of compound in system；N is binding site number.Three kinds of compounds are with lg [(F0-
F)/F] it is ordinate, with lg [Q] for abscissa, Figure 10 that linear fit comes out can according to the slope of fitting a straight line and intercept
K is calculatedAWith the value of n.Calculated result is K of three kinds of compounds in conjunction with BSAARespectively 1.92 × 104、 8.06×
104With 1.76 × 105L·mol-1, binding site is respectively 0.78,0.89 and 0.95, all close to 1, illustrate compound with
The combination ratio of BSA is close to 1:1.The result shows that three kinds of compounds are shown and the good binding affinity of BSA.
The bacteriostatic activity test of 7: three kinds of compounds of embodiment
Use the antibacterial activity of cylinder plate method test target compound.4 kinds of pathogens, i.e. Escherichia coli are chosen in experiment
(E.coli), staphylococcus aureus (S.aureus), bacillus subtilis (B.subtilis) and pseudomonas aeruginosa
(P.aeruginosa).The concentration for testing primary election compound is 500 μ g/mL, is then measured using doubling dilution minimum antibacterial
Concentration.Carry disease germs the production of plate: lower layer uses agar medium, and upper layer is using the nutrient agar for being mixed into test organisms.?
Media surface vertically puts Oxford cup, is added 200 μ L of measuring samples in cup, 37 DEG C culture 16-18 hours, measurement inhibition zone
Size.If diameter is greater than 8mm, determine that there is bacteriostatic activity.In triplicate, antibacterial result takes its average value for experiment.Experiment
In positive control use gentamicin sulphate, negative control use 20%DMF (VDMF:VWater=1:4).
The origin of the antibacterial activity and inhibition zone of testing compound be attributable to they bactericidal effect (kill bacterium) or
Bacteriostasis (inhibits bacterial reproduction by blocking bacterial cell surface or intracellular active site).500 μ g/mL concentration
Under, three kinds of compounds are as shown in figure 11 to the extracorporeal extracorporeal suppression of 4 kinds of test organisms, and the lower three kinds of compounds of 5 concentration are to test organisms
Antibacterial circle diameter data be shown in Table 2.The experimental results showed that three kinds of compounds have a degree of inhibition to imitate 4 kinds of test organisms
Fruit takes second place to staphylococcus aureus wherein the inhibitory effect of III pair of bacillus subtilis is optimal, when concentration is 500 μ g/mL
When, inhibition zone respectively reaches 16.9mm and 15.6mm.According to table 2, III pair of bacillus subtilis and staphylococcus aureus
Minimal inhibitory concentration (MIC) be 62.5 μ g/mL, and others MIC it is equal >=125 μ g/mL.
Table 2 be structure 1, structure II, III 3 kinds of compounds of structure antibacterial circle diameter
"-"=no activity
Claims (10)
1. a kind of pyridines hydrazone compound, it is characterised in that structure are as follows:
R is halogen.
2. a kind of pyridines hydrazone compound monocrystalline, it is characterised in that: the length of monoclinic system, Cc space group, crystallographic axis is respectivelyInterplanar angle is respectively α=90.00 °, and β=
93.842 (5) °, γ=90.00 °, cell volumeMolecular number Z=4 in elementary cell, elementary cell
In electron number F (000)=600, density Dc=1.476gcm-3, structure are as follows:
3. a kind of pyridines hydrazone compound monocrystalline, it is characterised in that: the length of monoclinic system, Cc space group, crystallographic axis is respectivelyInterplanar angle is respectively α=90.00 °, and β=
93.814 (5) °, γ=90.00 °, cell volumeMolecular number Z=4 in elementary cell, elementary cell
In electron number F (000)=672, density Dc=1.677gcm-3, structure are as follows:
4. a kind of pyridines hydrazone compound monocrystalline, it is characterised in that: the length of monoclinic system, Cc space group, crystallographic axis is respectivelyInterplanar angle be respectively α=
90.00 °, β=93.956 (3) °, γ=90.00 °, cell volumeMolecular number Z=in elementary cell
4, electron number F (000)=744, density D in elementary cellc=1.852gcm-3, structure are as follows:
5. the synthetic method of pyridines hydrazone compound described in a kind of claim 1, it is characterised in that the following steps are included:
1) 4- chloropyridine -2- formylhydrazine is synthesized:
2) 4- chloropyridine -2- formylhydrazine is dissolved in organic solvent, obtains solution 1；
3) p- halobenzene formaldehyde is dissolved in organic solvent, obtains solution 2；
4) solution 2 is added in solution 1, is flowed back after a few houres under 60 DEG C of -80 DEG C of stirrings, filtering, filtrate generates after standing
White crystalline pyridines hydrazone compound.
6. the synthetic method of pyridines hydrazone compound according to claim 5, it is characterised in that
Step 1) specifically:
It weighs after 4- chloropyridine -2- methyl formate is dissolved in organic solvent and obtains solution A, hydrazine hydrate, 65 DEG C of perseverances are added into solution A
After temperature stirs lower water-bath reflux 4h, stop heating, after be cooled to room temperature, have crystal precipitation after standing, with recrystallizing methanol, subtract
Pressure is dried after filtering, and obtains the 4- chloropyridine -2- formylhydrazine of white；
Step 2) specifically: 4- chloropyridine -2- formylhydrazine is dissolved in methanol or ethyl alcohol, obtains solution 1.
7. the synthetic method of pyridines hydrazone compound according to claim 6, it is characterised in that:
Step 3) specifically: p- chlorobenzaldehyde is dissolved in glacial acetic acid, obtains solution 2；
Step 4) specifically: solution 2 is added in solution 1, after 60 DEG C are stirred lower water-bath reflux 4h, is filtered while hot, filtrate chamber
The rhabdolith of a large amount of p- chlorobenzaldehyde -4- chloropyridine -2- formyl hydrazones of white is generated after standing one day under the conditions of temperature.
8. the synthetic method of pyridines hydrazone compound according to claim 6, it is characterised in that:
Step 3) specifically: p- bromobenzaldehyde is dissolved in ethyl alcohol, obtains solution 2；
Step 4) specifically: solution 2 is added in solution 1, after 80 DEG C are stirred lower water-bath reflux 4h, is filtered while hot, filtrate chamber
The rhabdolith for generating a large amount of p- bromobenzaldehyde -4- chloropyridine -2- formyl hydrazones of white two days later is stood under the conditions of temperature.
9. the synthetic method of pyridines hydrazone compound according to claim 6, it is characterised in that:
Step 3) specifically: p- benzaldehyde iodine is dissolved in glacial acetic acid, obtains solution 2；
Step 4) specifically: solution 2 is added in solution 1, after 80 DEG C are stirred lower water-bath reflux 4h, is filtered while hot, filtrate chamber
The rhabdolith for generating a large amount of p- benzaldehyde iodine benzaldehyde -4- chloropyridine -2- formyl hydrazones of white two days later is stood under the conditions of temperature.
10. any the pyridines hydrazone compound and DNA, BSA of claim 1-4 are there are certain interaction, right
Escherichia coli, staphylococcus aureus, bacillus subtilis and pseudomonas aeruginosa have inhibitory effect.
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| WO2010083316A2 (en) * | 2009-01-14 | 2010-07-22 | Dow Agrosciences Llc | Fungicidal compositions including hydrazone derivatives and copper |
| CN101874496A (en) * | 2010-06-30 | 2010-11-03 | 浙江工业大学 | Application of acyl hydrazone derivative as fungicide |
| CN103044284A (en) * | 2011-10-13 | 2013-04-17 | 南京大学 | Vanillic acid acylhydrazone derivatives, and preparation method and application thereof |
| CN103664690A (en) * | 2012-09-14 | 2014-03-26 | 南京大学 | Acylhydrazone derivatives of protocatechuic acid, and preparation method and antibacterial activity thereof |
| CN108840823A (en) * | 2018-06-06 | 2018-11-20 | 怀化学院 | A kind of synthetic method of icotinoylhydrazones Schiff bases compound and its application in fungicide |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010083316A2 (en) * | 2009-01-14 | 2010-07-22 | Dow Agrosciences Llc | Fungicidal compositions including hydrazone derivatives and copper |
| CN101874496A (en) * | 2010-06-30 | 2010-11-03 | 浙江工业大学 | Application of acyl hydrazone derivative as fungicide |
| CN103044284A (en) * | 2011-10-13 | 2013-04-17 | 南京大学 | Vanillic acid acylhydrazone derivatives, and preparation method and application thereof |
| CN103664690A (en) * | 2012-09-14 | 2014-03-26 | 南京大学 | Acylhydrazone derivatives of protocatechuic acid, and preparation method and antibacterial activity thereof |
| CN108840823A (en) * | 2018-06-06 | 2018-11-20 | 怀化学院 | A kind of synthetic method of icotinoylhydrazones Schiff bases compound and its application in fungicide |
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