CN101519375A - Antifungal pyrazoline-substituting compound and preparation method and application thereof - Google Patents
Antifungal pyrazoline-substituting compound and preparation method and application thereof Download PDFInfo
- Publication number
- CN101519375A CN101519375A CN200910103388A CN200910103388A CN101519375A CN 101519375 A CN101519375 A CN 101519375A CN 200910103388 A CN200910103388 A CN 200910103388A CN 200910103388 A CN200910103388 A CN 200910103388A CN 101519375 A CN101519375 A CN 101519375A
- Authority
- CN
- China
- Prior art keywords
- pyrazoline
- antifungal
- substituting compound
- general formula
- ethanoyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses an antifungal pyrazoline-substituting compound with a general formula (I), wherein all substitutional groups have the following definitions: R1 is (II); R2 and R4 are mutually independent as hydrogen, halogen, nitryl, methyl or methoxyl group; and R3 is phenyl, acetyl or benzoyl. The invention also discloses a preparation method of the pyrazoline-substituting compound and the application in the preparation of antifungal drugs.
Description
Technical field
The present invention relates to a kind of compound, particularly a kind of antifungal pyrazoline-substituting compound also relates to the preparation method and the application of this compound.
Background technology
Pyrazoline is very important nitrogenous five member ring heterocyclic compound, has stronger fluorescence property, in field widespread uses such as organic chemistry, photoelectricity, can be used as hole transport media in white dyes, photoelectric material and the electroluminescent system of organic synthesis raw material, yarn fabric and paper stock thing etc.In addition, bibliographical information pyrazoline and derivative thereof have desinsection, kill biological activitys such as mite, fungicidal, can also prevent and/or treat cell breeding disease, cardiovascular and cerebrovascular diseases, cancer etc.Pyrazoline-substituting, 5-hydroxypyrazoles quinoline, dicyclo 5-hydroxypyrazoles quinoline, the N-benzoyl-5-hydroxyl-5-phenylpyrrazolin of control plant pathogenic fungi have been disclosed among CN1066069A, CN 101184736A, CN 101184393A, the CN 101184392A; but the relevant report of preventing and treating the pyrazoline-substituting that causes the human disease fungi is few; and it is active and unsatisfactory; people still are devoted to it is carried out structure of modification, to seek more efficient, safe compound.
Summary of the invention
In view of this, for overcoming the deficiencies in the prior art, one of purpose of the present invention is to provide a kind of antifungal pyrazoline-substituting compound, can suppress to cause human disease's fungi growth and breeding, is used for the treatment of human fungal disease.
For reaching this purpose, the invention provides a kind of antifungal pyrazoline-substituting compound, it is characterized in that: have general formula (I):
Wherein each substituting group has following definition: R
1For
Or
R
2And R
4Be hydrogen, halogen, nitro, methyl or methoxy independently of each other; R
3Be phenyl, acetyl or benzoyl base.
Further, R
2Be halogen, nitro or methyl; R
4Be halogen, methyl or methoxy;
Further, be selected from the following compounds any:
1,3,5-triphenyl pyrazoline,
1-ethanoyl-3-p-methylphenyl-5-is to the fluorophenyl pyrazoline,
1-ethanoyl-3-rubigan-5-is to the fluorophenyl pyrazoline,
1-ethanoyl-3-rubigan-5-p-methylphenyl pyrazoline,
1-ethanoyl-3-furyl-5-p-nitrophenyl pyrazoline,
1-ethanoyl-3-furyl-5-is to the fluorophenyl pyrazoline,
1-benzoyl-3-p-methoxyphenyl-5-is to the bromophenyl pyrazoline,
1-benzoyl-3-p-methoxyphenyl-5-rubigan pyrazoline.
The term of Shi Yonging " halogen " has the common implication in present technique field in the present invention, promptly comprises fluorine, chlorine, bromine and iodine.
Two of purpose of the present invention is to provide the preparation method of described antifungal pyrazoline-substituting compound.
For reaching this purpose, the invention provides the preparation method of described antifungal pyrazoline-substituting compound: compound and phenylhydrazine with general formula (II) react in solvent, promptly make R in the general formula (I)
3Be the antifungal pyrazoline-substituting compound (IA) of phenyl, chemical equation is as follows:
(II) (IA)
Perhaps, have compound and the hydrazine hydrate and acetate (acetate is simultaneously as the solvent) reaction of general formula (II), promptly make R in the general formula (I)
3Be the antifungal pyrazoline-substituting compound (IB) of ethanoyl, chemical equation is as follows:
(II) (IB)
Perhaps, compound and hydrazine hydrate with general formula (II) react in solvent, make the have general formula compound of (III) earlier, with the Benzoyl chloride reaction, promptly make R in the general formula (I) again
3Be the antifungal pyrazoline-substituting compound (IC) of benzoyl, chemical equation is as follows:
(II) (III) (IC)
R in the above-mentioned general formula
1And R
2Has the aforementioned definition of giving.In the above-mentioned chemical equation, Ph represents phenyl, and Ac represents ethanoyl, and Et represents ethyl.
Further, to be selected from concentration expressed in percentage by volume be 90%～100% methanol aqueous solution, aqueous ethanolic solution or isopropanol water solution to described solvent;
Further, to be selected from concentration expressed in percentage by volume be 90%～100% aqueous ethanolic solution to described solvent.
Compound with general formula (II) is by known (the Organic Syntheses.Conard CR et al.2 of document, 167,1943.), perhaps can be prepared according to the document of being quoted, usually make R in the general formula by ketone with general formula (IV) and substituted benzoyl aldehyde reaction with logical formula V
1And R
2Has the aforementioned definition of giving.
(IV) (V) (II)
Three of purpose of the present invention is to provide the application of described antifungal pyrazoline-substituting compound.
For reaching this purpose, the invention provides the application of described antifungal pyrazoline-substituting compound in the preparation antifungal drug.
Further, described fungi is the Candida albicans bacterium.
Four of purpose of the present invention is to provide a kind of pharmaceutical composition.
For reaching this purpose, the invention provides a kind of pharmaceutical composition, contain described antifungal pyrazoline-substituting compound and pharmaceutically acceptable carrier.
Pyrazoline-substituting compound with anti-mycotic activity can be used as active constituents of medicine, become pharmaceutical composition with pharmaceutically acceptable vehicle group, can also have anti-mycotic activity or other active Chinese medical extract and/or chemical synthetic drug and pharmaceutically acceptable vehicle group with other and become pharmaceutical composition.Those of ordinary skills can determine the formulation of aforementioned pharmaceutical compositions at an easy rate, and are prepared according to the ordinary method of pharmaceutical field, and the gained pharmaceutical preparation can be used by the feasible approach of any facility.
Beneficial effect of the present invention is: the invention provides a kind of antifungal pyrazoline-substituting compound, can be prepared by simple and easy to do method, external antimycotic experimental result shows, it can suppress to cause human disease's fungi growth and breeding, the potential development and application values is arranged, can make antifungal drug, be used for the treatment of human fungal disease.
Embodiment
In order to make the purpose, technical solutions and advantages of the present invention clearer, below the preferred embodiments of the present invention are described in detail.
Embodiment 1,1,3, the preparation of 5-triphenyl pyrazoline
In the 50mL flask, adding methyl phenyl ketone 3g (0.025mol) and concentration expressed in percentage by volume are 95% ethanol 10mL, stir, the adding mass percentage concentration is 10% sodium hydroxide solution 12mL, under agitation condition, drip phenyl aldehyde 2.65g (0.025mol) again, dropwise stirring reaction under the room temperature of back, with thin-layer chromatography (TLC) method monitoring reaction process, afterreaction finished in 2 hours, suction filtration, and filter cake is washed with distilled water to neutrality, get thick product, with concentration expressed in percentage by volume is 95% ethyl alcohol recrystallization, the pure product 4.5g of benzylidene acetophenone, yield 86%;
In the 50mL flask, add benzylidene acetophenone 0.516g (0.002mol), dehydrated alcohol 25mL and phenylhydrazine 0.216g (0.002mol), heating reflux reaction, with TLC method monitoring reaction process, 2.5 hour afterreaction finishes, cooling gets thick product, use the dehydrated alcohol recrystallization, get white needle-like crystals 0.4g, yield 67.1% is 1 through fusing point (mp) and nucleus magnetic resonance (NMR) conclusive evidence, 3,5-triphenyl pyrazoline: mp142.9～143.5 ℃;
1H NMR (CDCl
3) δ: 3.15 (1H, q), 3.85 (1H, q), 5.28 (1H, q), 6.80 (1H, s), 6.09 (2H, d, J=7.83), 7.19 (2H, t, J=8.42), 7.36 (8H, m), 7.74 (2H, d, J=7.03);
13C NMR (CDCl
3) δ: 43.40,64.59,105.08,113.39,119.32,125.38,125.82,126.87,127.16,127.66,127.82,129.00,131.26,134.25,142.33,144.57,145.52.
Embodiment 2,1-ethanoyl-3-p-methylphenyl-5-is to the preparation of fluorophenyl pyrazoline
In the 50mL flask, adding p-methyl aceto phenone 3.35g (0.025mol) and concentration expressed in percentage by volume are 95% ethanol 10mL, stir, the adding mass percentage concentration is 10% sodium hydroxide solution 12mL, under agitation condition, drip p-Fluorobenzenecarboxaldehyde 3g (0.025mol) again, dropwise stirring reaction under the room temperature of back, with TLC method monitoring reaction process, 2.5 hour afterreaction finishes, suction filtration, and filter cake is washed with distilled water to neutrality, get thick product, with concentration expressed in percentage by volume is 95% ethyl alcohol recrystallization, must be to the fluorobenzene methylene radical to the pure product 5.40g of toluene ethyl ketone, yield 90%;
In the 50mL flask; adding to the fluorobenzene methylene radical to toluene ethyl ketone 1.20g (0.005mol) and glacial acetic acid 20mL; stirring makes dissolving; under ice bath, drip hydrazine hydrate 3mL again; dropwise the post-heating back flow reaction; with TLC method monitoring reaction process; afterreaction finished in 5 hours, was cooled to room temperature, regulated pH to neutral with saturated sodium bicarbonate solution; leave standstill under 0～5 ℃ of condition of temperature; separating out solid, is 95% ethyl alcohol recrystallization with concentration expressed in percentage by volume, white needle-like crystals 1.03g; yield 70%, through NMR conclusive evidence for 1-ethanoyl-3-p-methylphenyl-5-to the fluorophenyl pyrazoline:
1H NMR (CDCl
3) δ: 2.41 (6H, m), 3.12 (1H, q), 3.73 (1H, q), 5.55 (1H, q), 6.99 (2H, t, J=8.53), 7.23 (4H, m), 7.78 (2H, d, J=7.78);
13C NMR (CDCl
3) δ: 21.45,21.90,42.30,59.15,115.68,126.51,127.54,128.45,129.44,137.73,140.76,153.83,160.45,163.71,168.77.
The preparation of embodiment 3,1-ethanoyl-3-furyl-5-p-nitrophenyl pyrazoline
In the 50mL flask, adding 2-acetyl furan 2.75g (0.025mol) and concentration expressed in percentage by volume are 95% ethanol 10mL, stir, the adding mass percentage concentration is 10% sodium hydroxide solution 12mL, under agitation condition, drip paranitrobenzaldehyde 3.78g (0.025mol) again, dropwise stirring reaction under the room temperature of back, with TLC method monitoring reaction process, 2.5 hour afterreaction finishes, suction filtration, and filter cake is washed with distilled water to neutrality, get thick product, with concentration expressed in percentage by volume is 95% ethyl alcohol recrystallization, the pure product 5.10g of p-nitrophenyl methylene radical furyl ethyl ketone, yield 84%;
In the 50mL flask; add p-nitrophenyl methylene radical furyl ethyl ketone 1.22g (0.005mol) and glacial acetic acid 20mL; stirring makes dissolving; under ice bath, drip hydrazine hydrate 3mL again; dropwise the post-heating back flow reaction; with TLC method monitoring reaction process; afterreaction finished in 6 hours, was cooled to room temperature, regulated pH to neutral with saturated sodium bicarbonate solution; leave standstill under the temperature 0-5 ℃ of condition; separating out solid, is 95% ethyl alcohol recrystallization with concentration expressed in percentage by volume, white needle-like crystals 1.12g; yield 75%, through NMR conclusive evidence for 1-ethanoyl-3-p-methylphenyl-5-to the fluorophenyl pyrazoline:
1H NMR (CDCl
3) δ: 2.42 (3H, s), 3.11 (1H, q), 3.78 (1H, q), 5.63 (1H, q), 6.54 (1H, s), 6.78 (2H, d), 7.40 (2H, d), 7.58 (1H, s), 8.18 (2H, d).
13C NMR (CDCl
3) δ: 21.78,41.68,58.89,112.03,112.97,124.25,126.59,144.98,145.34,146.25,147.30,148.43,168.91.
Embodiment 4,1-benzoyl-3-p-methoxyphenyl-5-is to the preparation of bromophenyl pyrazoline
In the 50mL flask, adding p-methoxy-acetophenone 3.75g (0.025mol) and concentration expressed in percentage by volume are 95% ethanol 10mL, stir, the adding mass percentage concentration is 10% sodium hydroxide solution 12mL, under agitation condition, drip p-bromobenzaldehyde 4.63g (0.025mol) again, dropwise stirring reaction under the room temperature of back, with TLC method monitoring reaction process, afterreaction finished in 3 hours, suction filtration, and filter cake is washed with distilled water to neutrality, get thick product, with concentration expressed in percentage by volume is 95% ethyl alcohol recrystallization, must be to the pure product 4.61g of bromobenzene methylene radical p-methoxy-acetophenone, yield 85%;
In the 50mL flask, adding bromobenzene methylene radical p-methoxy-acetophenone 1.58g (0.005mol), concentration expressed in percentage by volume is that 90% ethanol 20mL and concentration expressed in percentage by volume are 80% hydrazine hydrate 5mL, heating reflux reaction, with TLC method monitoring reaction process, afterreaction finished in 1.5 hours, cooling, remove ethanol, add ether, washing, anhydrous magnesium sulfate drying, suction filtration, the filtrate decompression distillation removes desolvates, and gets 3-p-methoxyphenyl-5-to the bromophenyl pyrazoline, is directly used in the next step;
Gained 3-p-methoxyphenyl-5-to the bromophenyl pyrazoline in; add Benzoyl chloride 3mL (excessive); 50 ℃ of reactions of temperature 30 minutes, cooling adds methyl alcohol 10mL; cooling; separate out solid, use recrystallizing methanol, get white crystal 1.2g; yield 55.3%, through NMR conclusive evidence for 1-benzoyl-3-p-methoxyphenyl-5-to the bromophenyl pyrazoline:
1H NMR (CDCl
3) δ: 3.13 (1H, q), 3.84 (3H, s), 5.75 (1H, q), 6.92 (2H, d, J=8.61), 7.23 (2H, d, J=8.43), 7.46 (5H, m), 7.64 (2H, d, J=8.64), 8.02 (2H, d, J=7.02);
13C NMR (CDCl
3) δ: 41.44,55.39,60.65,114.19,121.52,123.79,127.58,128.38,130.10,130.95,132.04,134.21,141.00,154.28,161.50,166.15.
With reference to the foregoing description 1 to 4, can synthesize other pyrazoline-substituting compound of the present invention, and, making in the reaction of pyrazoline-substituting compound of the present invention by general formula (II) compound, it is 90%～100% methanol aqueous solution, aqueous ethanolic solution or isopropanol water solution that solvent can be selected from concentration expressed in percentage by volume, can reach the object of the invention.
The extracorporeal antifungal activity of part pyrazoline-substituting compound of the present invention
The Candida albicans bacterium (Candidaalbicans) claim Candida albicans again, it is a kind of modal condition pathogenic fungus, usually be present in human oral, gi tract and the reproductive tract, when normal microflora imbalance or resistibility reduction, the many positions of human body be can invade, mucocutaneous infections (common white mouth, vaginitis), visceralization (pneumonia, sacroiliitis, urocystitis, pyelonephritis), nervus centralis infection (meningitis, encephalitis, cerebral abscess) etc. caused.The present invention is representative with the Candida albicans bacterium, has investigated the extracorporeal antifungal activity of part pyrazoline-substituting compound.
The Candida albicans bacterium is inoculated in husky fort agar slant, after 37 ℃ of temperature are cultivated 24 hours, the physiological saline washing, being mixed with cell density with turbidimetry is 10
5The bacterium liquid of cfu/mL; With the fluconazole acetone solution, make the solution that concentration is 500 μ g/mL, in contrast product solution; Part pyrazoline-substituting compound of the present invention (compound 1～6) is used acetone solution, make the solution that concentration is 500 μ g/mL, as sample solution; Cut-off directly is the filter paper of 6.35mm, soaks certain hour in reference substance solution or sample solution 10 μ L, makes the pastille scraps of paper; With cell density is 10
5The bacterium liquid of cfu/mL evenly is applied on the husky fort agar plate, treat that bacterium liquid is done after, 3 on the overlapping thereon placement pastille scraps of paper, temperature was cultivated 48 hours for 37 ℃, measured antibacterial ring.The results are shown in subordinate list, by subordinate list as can be known, compound 1～6 dialogue candidiasis is all inhibited.
The external antimycotic experimental result of subordinate list, part pyrazoline-substituting compound of the present invention
Explanation is at last, above embodiment is only unrestricted in order to technical scheme of the present invention to be described, although by invention has been described with reference to the preferred embodiments of the present invention, but those of ordinary skill in the art is to be understood that, can make various changes to it in the form and details, and the spirit and scope of the present invention that do not depart from appended claims and limited.
Claims (9)
1, antifungal pyrazoline-substituting compound is characterized in that: have general formula (I):
Wherein each substituting group has following definition: R
1For
R
2And R
4Be hydrogen, halogen, nitro, methyl or methoxy independently of each other; R
3Be phenyl, acetyl or benzoyl base.
2, antifungal pyrazoline-substituting compound according to claim 1 is characterized in that: R
2Be halogen, nitro or methyl; R
4Be halogen, methyl or methoxy.
3, antifungal pyrazoline-substituting compound according to claim 2 is characterized in that: be selected from the following compounds any:
1,3,5-triphenyl pyrazoline,
1-ethanoyl-3-p-methylphenyl-5-is to the fluorophenyl pyrazoline,
1-ethanoyl-3-rubigan-5-is to the fluorophenyl pyrazoline,
1-ethanoyl-3-rubigan-5-p-methylphenyl pyrazoline,
1-ethanoyl-3-furyl-5-p-nitrophenyl pyrazoline,
1-ethanoyl-3-furyl-5-is to the fluorophenyl pyrazoline,
1-benzoyl-3-p-methoxyphenyl-5-is to the bromophenyl pyrazoline,
1-benzoyl-3-p-methoxyphenyl-5-rubigan pyrazoline.
4, the preparation method of the described antifungal pyrazoline-substituting compound of claim 1 is characterized in that: compound and phenylhydrazine with general formula (II) react in solvent, promptly make R in the general formula (I)
3Be the antifungal pyrazoline-substituting compound (IA) of phenyl, chemical equation is as follows:
Perhaps, have compound and the hydrazine hydrate and the acetic acidreaction of general formula (II), promptly make R in the general formula (I)
3Be the antifungal pyrazoline-substituting compound (IB) of ethanoyl, chemical equation is as follows:
Perhaps, compound and hydrazine hydrate with general formula (II) react in solvent, make the have general formula compound of (III) earlier, with the Benzoyl chloride reaction, promptly make R in the general formula (I) again
3Be the antifungal pyrazoline-substituting compound (IC) of benzoyl, chemical equation is as follows:
R in the above-mentioned general formula
1And R
2Have and give definition in the claim 1.
5, the preparation method of antifungal pyrazoline-substituting compound according to claim 4 is characterized in that: it is 90%～100% methanol aqueous solution, aqueous ethanolic solution or isopropanol water solution that described solvent is selected from concentration expressed in percentage by volume.
6, the preparation method of antifungal pyrazoline-substituting compound according to claim 5 is characterized in that: it is 90%～100% aqueous ethanolic solution that described solvent is selected from concentration expressed in percentage by volume.
7, the application of the described antifungal pyrazoline-substituting compound of claim 1 in the preparation antifungal drug.
8, the application of antifungal pyrazoline-substituting compound according to claim 7 is characterized in that: described fungi is the Candida albicans bacterium.
9, pharmaceutical composition is characterized in that: contain described antifungal pyrazoline-substituting compound of claim 1 and pharmaceutically acceptable carrier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101033887A CN101519375B (en) | 2009-03-16 | 2009-03-16 | Antifungal pyrazoline-substituting compound and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009101033887A CN101519375B (en) | 2009-03-16 | 2009-03-16 | Antifungal pyrazoline-substituting compound and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101519375A true CN101519375A (en) | 2009-09-02 |
| CN101519375B CN101519375B (en) | 2011-12-07 |
Family
ID=41080198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009101033887A Expired - Fee Related CN101519375B (en) | 2009-03-16 | 2009-03-16 | Antifungal pyrazoline-substituting compound and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101519375B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102863951A (en) * | 2012-10-23 | 2013-01-09 | 新疆大学 | Preparation method of pyrazolone/fluorescent dye self-assembling heterostructure material |
| CN104292164A (en) * | 2014-09-22 | 2015-01-21 | 华中师范大学 | Dihydropyrazole compounds, and preparation method and application thereof |
| CN113264949A (en) * | 2021-05-31 | 2021-08-17 | 西南大学 | Design synthesis and application of spirobenzoxazine piperidine alpha, beta-unsaturated ketone derivatives |
-
2009
- 2009-03-16 CN CN2009101033887A patent/CN101519375B/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102863951A (en) * | 2012-10-23 | 2013-01-09 | 新疆大学 | Preparation method of pyrazolone/fluorescent dye self-assembling heterostructure material |
| CN104292164A (en) * | 2014-09-22 | 2015-01-21 | 华中师范大学 | Dihydropyrazole compounds, and preparation method and application thereof |
| CN104292164B (en) * | 2014-09-22 | 2017-03-22 | 华中师范大学 | Dihydropyrazole compounds, and preparation method and application thereof |
| CN113264949A (en) * | 2021-05-31 | 2021-08-17 | 西南大学 | Design synthesis and application of spirobenzoxazine piperidine alpha, beta-unsaturated ketone derivatives |
| CN113264949B (en) * | 2021-05-31 | 2022-04-05 | 西南大学 | Design synthesis and application of spirobenzoxazine piperidine alpha, beta-unsaturated ketone derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101519375B (en) | 2011-12-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102796052B (en) | Paeonol-1,2,3-triazole compound having antifungal activity and preparation method thereof | |
| Salih et al. | Synthesis and antimicrobial activities of 9H-carbazole derivatives | |
| CN106588911B (en) | A kind of novel thiazole class compound XQH-3-6 of Streptococcus mutans and its application | |
| CN104829608B (en) | A kind of cumarin thiazole indolone type compound and its preparation method and purposes | |
| CN103059006B (en) | Chrysin-1,2,3-triazole compound with anti-microbial activity and preparation method thereof | |
| CN105481706A (en) | 2-hydroxyl chalcone compound as well as preparation method and purpose thereof | |
| CN101519375B (en) | Antifungal pyrazoline-substituting compound and preparation method and application thereof | |
| CN104059027A (en) | (E)-methyl 2-methoxyiminobenzeneacetate compound containing 1, 2, 4-triazole and preparation method and application thereof | |
| CN105859537B (en) | Open loop hill gooseberry's keto analog and preparation method thereof and the application in antibacterials | |
| CN108530435B (en) | Quinoxaline-containing 1, 4-pentadiene-3-ketone derivative, preparation method and application | |
| DE1598092A1 (en) | Methods and diagnostic means for the detection of bacteria | |
| CN104860909A (en) | Griseofulvin derivative, griseofulvin, and application of griseofulvin derivative in antibacterial activity | |
| CN110526910B (en) | Thiazole orange benzyl quaternary ammonium salt derivative and preparation method and application thereof | |
| CN105924397B (en) | A kind of formic acid esters pyrazole compound of 1,5 diaryl 3, Preparation method and use | |
| CN102796080B (en) | A kind of novel azole antifungal compound and its preparation method and application | |
| CN101367800A (en) | Synthesis of tubercle bacillus resistant medicament 3-alkoxyl-8-alkyl -12-R3-jatrorrhizine salt and uses thereof | |
| CN105541853B (en) | The γ pyrans pyrrolizine assimilation compound and preparation method and purposes of multi-substituent type | |
| JPS5815937A (en) | Phlorophenone derivative, manufacture, use and pharmaceutical composition of phlorophenone compound | |
| CN104003924B (en) | N-replaces-3-[3-(substituted-phenyl)-2-alkene-1-ketone]-4-hydroxypyrrole quinoline-2-ketone compounds and preparation method and application | |
| CN109111397B (en) | Quinoline aromatic ethylene derivative and preparation method and application thereof | |
| CN109111396B (en) | Quinoline aromatic vinyl derivative and preparation method and application thereof | |
| CN102993115B (en) | A kind of 3,5 – bis-substituted isoxazoles quinoline derivants and synthetic method thereof and application | |
| CN108456157B (en) | 1-substituted benzoyl-4-fatty acyl semicarbazide derivatives, preparation method and application as antibacterial drugs | |
| CN114957238B (en) | 3-hydroxy-pyrrole-2-ketone compound containing 1,3, 4-thiadiazole and synthetic method and application thereof | |
| CN115784848B (en) | Nor-Aronia melanocarpa derivatives, and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20111207 Termination date: 20140316 |