CN110229081A - 2,4- dinitrobenzene hydazone derivative and the preparation method and application thereof - Google Patents

2,4- dinitrobenzene hydazone derivative and the preparation method and application thereof Download PDF

Info

Publication number
CN110229081A
CN110229081A CN201910585002.4A CN201910585002A CN110229081A CN 110229081 A CN110229081 A CN 110229081A CN 201910585002 A CN201910585002 A CN 201910585002A CN 110229081 A CN110229081 A CN 110229081A
Authority
CN
China
Prior art keywords
hydroxyl
ethyoxyl
methoxyl group
dihydroxy
hydroxy
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
Application number
CN201910585002.4A
Other languages
Chinese (zh)
Other versions
CN110229081B (en
Inventor
陈平
陈爱羽
胡艾希
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Changsha University of Science and Technology
Original Assignee
Changsha University of Science and Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Changsha University of Science and Technology filed Critical Changsha University of Science and Technology
Priority to CN201910585002.4A priority Critical patent/CN110229081B/en
Publication of CN110229081A publication Critical patent/CN110229081A/en
Application granted granted Critical
Publication of CN110229081B publication Critical patent/CN110229081B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings

Abstract

The present invention relates to 2,4- dinitrobenzene hydazone derivative and its pharmaceutically acceptable salt shown in chemical structural formula I, pharmaceutical composition and its preparing the application in influenza virus neuraminidase inhibitor:

Description

2,4- dinitrobenzene hydazone derivative and the preparation method and application thereof
Technical field
The present invention relates to a kind of noval chemical compound, preparation method and application, specifically 2,4- dinitrobenzene hydazone derivative, its Preparation method and its in the application for preparing influenza virus neuraminidase inhibitor.
Background technique
Hydrazone (Hydrazone) class compound is to be obtained by aldehydes or ketones class compound and hydrazine class compound by dehydrating condensation Schiff base compound contains imino group and time amino groups [Asian Journal of Pharmacy and Pharmacology,2018,4(2):116-122].Fragrant hydrazone compounds have extensive bioactivity, such as antiviral, anti- The bioactivity such as depressed, antitumor, antibacterial, anti-inflammatory, anti-malarial, analgesia, anti-platelet aggregation and blood vessel dilatation.
2003, Jarikote etc. [Ultrasonics Sonochemistry, 2003,10 (1): 45-48] was not being added In the case where catalyst, by reacting phenylhydrazine under ultrasonic radiation with carbonyls, aryl hydrazone compounds have been synthesized:
2010, Ajani etc. [Bioorganic&Medicinal Chemistry, 2010,18 (1): 214-221] description The cyclohexanone of -2 (1H) -one of 3- diazanyl quinoxaline and 2 substitutions, by microwave irradiation technology have synthesized 2- quinokysalines -3- Hydazone derivative, and have rated its antibacterial activity:
2014, Oliveira etc. [RSC Advances, 2014,4 (100): 56736-56742] describe organic hydrazine and Benzaldehyde derivative has synthesized a series of hydrazone compounds by no catalyst and solvent-free mechanochemistry approach:
2015, Parveen etc. [New Journal of Chemistry, 2015,39 (1): 469-481] described water Hydrazine and substituted aromatic aldehyde are closed, in ionic liquid [Et3NH][HSO4] fragrant double hydazone derivatives have been synthesized under catalyst:
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of 2,4- dinitrobenzene hydazone derivatives, preparation method, medicine group Close object and purposes.
To solve technical problem of the invention, the invention provides the following technical scheme:
There is provided a kind of 2,4- dinitrobenzene hydazone derivatives as shown in structural formula I for the first aspect of technical solution of the present invention And its pharmaceutically acceptable salt:
Wherein, Y is selected from: 2- hydroxyl, 3- hydroxyl, 4- hydroxyl, 2,4- dihydroxy, 3,4- dihydroxy, 2,5- dihydroxy, 3,5- Dihydroxy, 2,6- dihydroxy, 2- hydroxy-3-methoxy, 2- hydroxyl -4- methoxyl group, 2- hydroxy-5-methyl oxygroup, 2- hydroxyl -6- first Oxygroup, 3- hydroxyl -2- methoxyl group, 3- hydroxyl -4- methoxyl group, 3- hydroxy-5-methyl oxygroup, 3- hydroxyl -6- methoxyl group, 4- hydroxyl - 2- methoxyl group, 4- hydroxy-3-methoxy, 4- hydroxyl -3,5- dimethoxy, 2- hydroxyl -3- ethyoxyl, 2- hydroxyl -4- ethyoxyl, 2- hydroxyl -5- ethyoxyl, 2- hydroxyl -6- ethyoxyl, 3- hydroxyl -2- ethyoxyl, 3- hydroxyl -4- ethyoxyl, 3- hydroxyl -5- ethoxy Base, 3- hydroxyl -6- ethyoxyl, 4- hydroxyl -2- ethyoxyl, 4- hydroxyl -3- ethyoxyl, 4- hydroxyl -3,5- diethoxy, 2,3,4- Trihydroxy or 4- hydroxyl -3,5- dimethyl.
Further, preferred compound is selected from: 4- hydroxy benzaldehyde -2,4- dinitrophenylhydrazone, 3- methoxyl group -4- hydroxyl Benzaldehyde -2,4- dinitrophenylhydrazone, 3,4- 4-dihydroxy benzaldehyde -2,4- dinitrophenylhydrazone or 2,4- 4-dihydroxy benzaldehyde -2,4- Dinitrophenylhydrazone.
There is provided the preparation method of 2,4- dinitrobenzene hydazone derivative, features for the second aspect of technical solution of the present invention It is that its preparation reaction is as follows:
Wherein, Y is selected from: 2- hydroxyl, 3- hydroxyl, 4- hydroxyl, 2,4- dihydroxy, 3,4- dihydroxy, 2,5- dihydroxy, 3,5- Dihydroxy, 2,6- dihydroxy, 2- hydroxy-3-methoxy, 2- hydroxyl -4- methoxyl group, 2- hydroxy-5-methyl oxygroup, 2- hydroxyl -6- first Oxygroup, 3- hydroxyl -2- methoxyl group, 3- hydroxyl -4- methoxyl group, 3- hydroxy-5-methyl oxygroup, 3- hydroxyl -6- methoxyl group, 4- hydroxyl - 2- methoxyl group, 4- hydroxy-3-methoxy, 4- hydroxyl -3,5- dimethoxy, 2- hydroxyl -3- ethyoxyl, 2- hydroxyl -4- ethyoxyl, 2- hydroxyl -5- ethyoxyl, 2- hydroxyl -6- ethyoxyl, 3- hydroxyl -2- ethyoxyl, 3- hydroxyl -4- ethyoxyl, 3- hydroxyl -5- ethoxy Base, 3- hydroxyl -6- ethyoxyl, 4- hydroxyl -2- ethyoxyl, 4- hydroxyl -3- ethyoxyl, 4- hydroxyl -3,5- diethoxy, 2,3,4- Trihydroxy or 4- hydroxyl -3,5- dimethyl.
The third aspect of technical solution of the present invention, which is to provide, contains compound described in first aspect and its pharmaceutically acceptable Salt pharmaceutical composition, the pharmaceutical composition contain therapeutically effective amount 2,4- dinitrobenzene hydazone derivative of the invention and its Pharmaceutically acceptable salt, and optional contain pharmaceutical carrier.Wherein the pharmaceutical carrier refers to the common medicine of pharmaceutical field Use carrier；The pharmaceutical composition can be prepared according to method well known in the art.It can be by by the compounds of this invention and its pharmaceutically Acceptable salt is combined with one or more pharmaceutically acceptable solids or liquid excipient and/or adjuvant, is made suitable for people Or any dosage form that animal uses.The content of the compounds of this invention and its pharmaceutically acceptable salt in its pharmaceutical composition is logical It is often 0.1%~95% weight percent.
The compounds of this invention and its pharmaceutically acceptable salt can be in a unit containing its pharmaceutical composition Administration, administration route can be enteron aisle or non-bowel, and such as oral, intravenous injection, intramuscular injection, subcutaneous injection, nasal cavity, oral cavity are viscous Film, eye, lung and respiratory tract, skin, vagina, rectum etc..
Form of administration can be liquid dosage form, solid dosage forms or semisolid dosage form.Liquid dosage form can be solution (including True solution and colloidal solution), emulsion (including o/w type, w/o type and emulsion), suspension, injection (including liquid drugs injection, powder-injection And infusion), eye drops, nasal drop, lotion and liniment etc.；Solid dosage forms can be tablet (including ordinary tablet, enteric coatel tablets, lozenge, Dispersible tablet, chewable tablets, effervescent tablet, oral disnitegration tablet), capsule (including hard capsule, soft capsule, capsulae enterosolubilis), granule, dissipate Agent, pellet, dripping pill, suppository, film, patch, the agent of gas (powder) mist, spray etc.；Semisolid dosage form can be ointment, gel Agent, paste etc..
It is sustained release preparation, control that the compounds of this invention and its pharmaceutically acceptable salt, which can be made ordinary preparation, also be made, Release formulation, targeting preparation and various particulate delivery systems.
In order to which tablet is made in the compounds of this invention and its pharmaceutically acceptable salt, can be widely used known in this field Various excipient, including diluent, binder, wetting agent, disintegrating agent, lubricant, glidant.Diluent can be starch, Dextrin, sucrose, glucose, lactose, mannitol, sorbierite, xylitol, microcrystalline cellulose, calcium sulfate, calcium monohydrogen phosphate, calcium carbonate Deng；Wetting agent can be water, ethyl alcohol, isopropanol etc.；Adhesive can be starch slurry, dextrin, syrup, honey, glucose solution, Microcrystalline cellulose, mucialga of arabic gummy, gelatine size, sodium carboxymethylcellulose, methylcellulose, hydroxypropyl methyl cellulose, ethyl Cellulose, acrylic resin, carbomer, polyvinylpyrrolidone, polyethylene glycol etc.；It is fine that disintegrating agent can be dried starch, crystallite Tie up element, low-substituted hydroxypropyl cellulose, crosslinked polyvinylpyrrolidone, croscarmellose sodium, sodium carboxymethyl starch, carbon Sour hydrogen sodium and citric acid, polyoxyethylene sorbitol aliphatic ester, dodecyl sodium sulfate etc.；Lubricant and glidant can be Talcum powder, silica, stearate, tartaric acid, atoleine, polyethylene glycol etc..
Tablet can also be further made to coating tablet, such as sugar coated tablet, thin membrane coated tablet, enteric coated tablets or double Synusia and multilayer tablet.
It, can be by effective component the compounds of this invention and its pharmaceutically acceptable in order to which capsule is made in administration unit Salt is mixed with diluent, glidant, and mixture is placed directly in hard capsule or soft capsule.It can also be by the effective component present inventionization Close object and its pharmaceutically acceptable salt and particle or pellet first be made with diluent, binder, disintegrating agent, then be placed in hard capsule or In soft capsule.It is used to prepare the compounds of this invention and its each diluent of pharmaceutically acceptable salt tablet, binder, wetting Agent, disintegrating agent, glidant kind can also be used for preparing the capsule of the compounds of this invention and its pharmaceutically acceptable salt.
For injection is made in the compounds of this invention and its pharmaceutically acceptable salt, can with water, ethyl alcohol, isopropanol, Simultaneously appropriate solubilizer commonly used in the art, cosolvent, pH adjustment agent, osmotic pressure is added in propylene glycol or their mixture as solvent Regulator.Solubilizer or cosolvent can be poloxamer, lecithin, hydroxypropyl-β-cyclodextrin etc.；PH adjustment agent can be phosphorus Hydrochlorate, acetate, hydrochloric acid, sodium hydroxide etc.；Osmotic pressure regulator can be sodium chloride, mannitol, glucose, phosphate, vinegar Hydrochlorate etc..Freeze drying powder injection is such as prepared, mannitol, glucose etc. can also be added as proppant.
In addition, if desired, colorant, preservative, fragrance, corrigent or other additions can also be added into pharmaceutical preparation Agent.
To reach medication purpose, enhance therapeutic effect, drug of the invention or pharmaceutical composition well known can be given with any The administration of prescription method.
The fourth aspect of technical solution of the present invention is to provide 2,4- dinitrobenzene hydazone derivative of the present invention and its pharmacy Upper acceptable salt and third aspect described pharmaceutical composition answering in terms of preparing influenza virus neuraminidase inhibitor With.
Advantageous effects:
2,4- dinitrobenzene hydazone derivative of the invention is a kind of change with influenza neuraminidase inhibitory activity Close object.
Specific embodiment
Following embodiment is intended to illustrate invention rather than limitation of the invention further.
Embodiment 1
The preparation of 4- hydroxy benzaldehyde -2,4- dinitrophenylhydrazone (A1)
1.0mmol2,4- dinitrophenylhydrazine and 1.05mmol4- hydroxy benzaldehyde are dissolved in 10mL ethyl alcohol, are stirred at room temperature 6h, TLC monitoring reaction.Reaction mixture is filtered, washs filter cake with petroleum ether and ethyl acetate mixtures (1:1), dry 4- hydroxy benzaldehyde -2,4- dinitrophenylhydrazone (A1), red solid, m.p.263~264 DEG C, yield 89.7%；1H NMR (400MHz, DMSO-d6) δ: 11.82 (s, 1H, NH), 9.94 (s, 1H, OH), 8.98 (d, J=2.5 Hz, 1H, C6H3), 8.34 (dd, J=9.3,2.5 Hz, 1H, C6H3), 8.12 (s, 1H, CH), 7.57 (d, J=8.4 Hz, 2H, C6H4), 7.26 (d, J= 9.3 Hz, 1H, C6H3), 6.83 (d, J=8.4 Hz, 2H, C6H4)；13C NMR (100 MHz, DMSO-d6) δ: 160.04, 150.08,144.61,136.89,130.06,129.71,125.12,123.78,123.40,116.90,116.11.
Embodiment 2
The preparation of Vanillin -2,4- dinitrophenylhydrazone (A2)
It prepares according to the method for embodiment 1,1.0mmol2,4- dinitrophenylhydrazine and 1.05mmol3- methoxyl group -4- hydroxyl Benzaldehyde reacts 6h, obtains Vanillin -2,4- dinitrophenylhydrazone (A2), red solid, m.p.266~267 DEG C, yield 96.1%；1H NMR (400 MHz, DMSO-d6) δ: 11.55 (s, 1H, NH), 9.69 (s, 1H, OH), 8.83 (s, 1H, CH), 8.54 (d, J=4.2 Hz, 1H, C6H3), 8.32 (d, J=9.6 Hz, 1H, C6H3), 8.06 (dd, J=9.6,4.2 Hz, 1H, C6H3), 7.36 (s, 1H, C6H3), 7.15 (d, J=8.1 Hz, 1H, C6H3), 6.86 (d, J=8.1 Hz, 1H, C6H3), 3.86 (s, 3H, CH3O)；13C NMR (100 MHz, DMSO-d6) δ: 150.16,149.65,148.11,144.40,136.53, 129.66,128.93,125.10,123.08,122.61,116.71,115.59,109.56,55.65.
Embodiment 3
The preparation of 3,4- 4-dihydroxy benzaldehyde -2,4- dinitrophenylhydrazone (A3)
It prepares according to the method for embodiment 1,1.0mmol2,4- dinitrophenylhydrazine and 1.05mmol3,4- 4-dihydroxy benzaldehyde 6h is reacted, 3,4- 4-dihydroxy benzaldehyde -2,4- dinitrophenylhydrazone (A3), red solid, m.p.272~273 DEG C, yield are obtained 91.2%；1H NMR (400 MHz, DMSO-d6) δ: 11.52 (s, 1H, NH), 9.58 (s, 1H, OH), 9.28 (s, 1H, OH), 8.85 (s, 1H, CH), 8.51 (d, J=3.0 Hz, 1H, C6H3), 8.36 (d, J=9.6 Hz, 1H, C6H3), 7.98 (dd, J= 9.6,3.0 Hz, 1H, C6H3), 7.24 (s, 1H, C6H3), 7.03 (d, J=8.1 Hz, 1H, C6H3), 6.82 (d, J=8.1 Hz, 1H, C6H3)；13C NMR (100 MHz, DMSO-d6) δ: 150.43,148.64,145.79,144.41,136.48,129.74, 128.87,125.12,123.15,120.94,116.41,115.74,113.31.
Embodiment 4
The preparation of 2,4- 4-dihydroxy benzaldehyde -2,4- dinitrophenylhydrazone (A4)
It prepares according to the method for embodiment 1,1.0mmol2,4- dinitrophenylhydrazine and 1.05mmol2,4- 4-dihydroxy benzaldehyde 6h is reacted, 2,4- 4-dihydroxy benzaldehyde -2,4- dinitrophenylhydrazone (A4), red solid, m.p. > 280 DEG C, yield 91.2% are obtained；1H NMR (400 MHz, DMSO-d6) δ: 11.57 (s, 1H, NH), 10.11 (s, 1H, OH), 9.94 (s, 1H, OH), 8.84 (s, 1H, C6H3), 8.79 (s, 1H, CH), 8.31 (d, J=9.6 Hz, 1H, C6H3), 7.93 (d, J=9.6 Hz, 1H, C6H3), 7.63 (d, J=9.2 Hz, 1H, C6H3), 6.35 (s, 1H, C6H3), 6.34 (d, J=9.2Hz, 1H, C6H3)；13C NMR (100 MHz, DMSO-d6) δ: 161.33,158.69,147.69,144.16,136.24,129.65,128.71,128.26,123.14, 116.38,111.51,108.19,102.39.
Embodiment 5
The resisiting influenza virus neuraminidase activity of 2,4- dinitrobenzene hydazone derivative
1. experimental principle
Compound MUNANA is the specific substrate of neuraminidase, the metabolite generated under neuraminic acid enzyme effect Under 360nm irradiation excitation, 450nm fluorescence can produce, the variation of fluorescence intensity can delicately react neuraminic acid enzyme activity Property.Enzyme both is from A/PR/8/34 (H1N1) virus stain.
2. experimental method
In enzyme reaction system, a certain concentration sample and influenza virus mind NA are suspended in reaction buffer (pH6.5), add Enter fluorogenic substrate MUNANA starting reaction system, 37 DEG C are incubated for after forty minutes, and reaction terminating liquid is added to terminate reaction.In excitation wavelength Under the Parameter Conditions that 360nm and launch wavelength are 450nm, fluorescence intensity level is measured.The fluorescence intensity of reaction system can reflect The activity of enzyme.Compound can be calculated to the active inhibiting rate of NA according to the reduction amount of fluorescence intensity.
3. test sample: embodiment compound
4. Activity Results
Compound is in reaction system to the inhibiting rate and IC of neuraminidase when 40.0 μ g/mL of detectable concentration50Value is included in Table 1.
Inhibitory activity and IC of the 1 2,4- dinitrobenzene hydazone derivative of table to neuraminidase H1N150
Compound Y Inhibiting rate (%) IC50(μg/mL)
A1 4-OH 73.08±8.21 18.39±2.91
A2 4-OH-3-OCH3 76.88±4.60 17.40±1.49
A3 3,4-(OH)2 41.53±2.60 -
A4 2,4-(OH)2 80.48±2.22 13.81±0.80
2,4- dinitrobenzene hydazone derivatives have resisiting influenza virus neuraminidase activity, can be used for preparing influenza virus mind Through propylhomoserin enzyme inhibitor.

Claims (5)

1. 2,4- dinitrobenzene hydazone derivative and its pharmaceutically acceptable salt shown in a kind of chemical structural formula I or II:
Wherein, Y is selected from: 2- hydroxyl, 3- hydroxyl, 4- hydroxyl, 2,4- dihydroxy, 3,4- dihydroxy, 2,5- dihydroxy, 3,5- dihydroxy Base, 2,6- dihydroxy, 2- hydroxy-3-methoxy, 2- hydroxyl -4- methoxyl group, 2- hydroxy-5-methyl oxygroup, 2- hydroxyl -6- methoxy Base, 3- hydroxyl -2- methoxyl group, 3- hydroxyl -4- methoxyl group, 3- hydroxy-5-methyl oxygroup, 3- hydroxyl -6- methoxyl group, 4- hydroxyl -2- Methoxyl group, 4- hydroxy-3-methoxy, 4- hydroxyl -3,5- dimethoxy, 2- hydroxyl -3- ethyoxyl, 2- hydroxyl -4- ethyoxyl, 2- Hydroxyl -5- ethyoxyl, 2- hydroxyl -6- ethyoxyl, 3- hydroxyl -2- ethyoxyl, 3- hydroxyl -4- ethyoxyl, 3- hydroxyl -5- ethoxy Base, 3- hydroxyl -6- ethyoxyl, 4- hydroxyl -2- ethyoxyl, 4- hydroxyl -3- ethyoxyl, 4- hydroxyl -3,5- diethoxy, 2,3,4- Trihydroxy or 4- hydroxyl -3,5- dimethyl.
2. one kind 2,4- dinitrobenzene hydazone derivative and its pharmaceutically acceptable salt are selected from following compounds:
4- hydroxy benzaldehyde -2,4- dinitrophenylhydrazone,
Vanillin -2,4- dinitrophenylhydrazone,
3,4- 4-dihydroxy benzaldehyde -2,4- dinitrophenylhydrazone or
2,4- 4-dihydroxy benzaldehyde -2,4- dinitrophenylhydrazone.
3. the preparation method of 2,4- dinitrobenzene hydazone derivative described in claim 1, which is characterized in that its preparation reaction is such as Under:
In formula, the definition of Y is as described in claim 1.
4. 2,4- dinitrobenzene hydazone derivative of any of claims 1 or 2 and its pharmaceutically acceptable salt are in preparation influenza Application in neuraminidase inhibitor.
5. available carrier at least one of a kind of pharmaceutical composition, including claims 1 or 2 compound and pharmaceutics.
CN201910585002.4A 2019-07-01 2019-07-01 2, 4-dinitrophenylhydrazone derivative and preparation method and application thereof Active CN110229081B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910585002.4A CN110229081B (en) 2019-07-01 2019-07-01 2, 4-dinitrophenylhydrazone derivative and preparation method and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910585002.4A CN110229081B (en) 2019-07-01 2019-07-01 2, 4-dinitrophenylhydrazone derivative and preparation method and application thereof

Publications (2)

Publication Number Publication Date
CN110229081A true CN110229081A (en) 2019-09-13
CN110229081B CN110229081B (en) 2022-02-08

Family

ID=67857913

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910585002.4A Active CN110229081B (en) 2019-07-01 2019-07-01 2, 4-dinitrophenylhydrazone derivative and preparation method and application thereof

Country Status (1)

Country Link
CN (1) CN110229081B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115160180A (en) * 2022-06-22 2022-10-11 广东海洋大学 Green synthesis method of vanillin shrinkage 2, 4-dinitrophenylhydrazone

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4670437A (en) * 1985-09-11 1987-06-02 Eli Lilly And Company Antiviral pyridazine hydrazones
UA6147A1 (en) * 1986-06-09 1994-12-29 Львівський Державний Медичний Інститут 2-(2',7'-diacetoxy-fluorenylidene-9'-hydrazono)-5-heptylidene-thiazolidone-4 exhibiting anti-influenza action against the influenza a and a-2 virus
UA6149A1 (en) * 1986-06-10 1994-12-29 Львівський Державний Медичний Інститут 2-(2',7'-diacetoxy-fluorenylidene-9'-hydrazono)-5-(n-nitrobenzylidene)-thiazolidone-4 exhibiting antiviral action against the influenza a and a-2 virus and vaccinia virus
US7341720B2 (en) * 2005-04-06 2008-03-11 Genzyme Corporation Targeting of glycoprotein therapeutics
CN101830854A (en) * 2009-03-09 2010-09-15 中国科学院上海药物研究所 Substituted phenylhydrazones compounds, preparation method and application thereof
WO2011113060A2 (en) * 2010-03-12 2011-09-15 Trana Discovery, Inc. Antiviral compounds and methods of use thereof
EP2004649B1 (en) * 2006-03-24 2012-07-04 The Feinstein Institute for Medical Research Phenolic hydrazone macrophage migration inhibitory factor inhibitors
CN104024849A (en) * 2011-08-12 2014-09-03 生命科技公司 Apparatuses, methods, computer program products, and kits for hi-throughput glycan analysis
CN105796545A (en) * 2016-05-25 2016-07-27 华中师范大学 Applications of hydrazone compound in preparing antifungal medicine
CN107987033A (en) * 2018-01-05 2018-05-04 湖南大学 The application of vanillic aldehyde and its isomers in NA inhibitor is prepared

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4670437A (en) * 1985-09-11 1987-06-02 Eli Lilly And Company Antiviral pyridazine hydrazones
UA6147A1 (en) * 1986-06-09 1994-12-29 Львівський Державний Медичний Інститут 2-(2',7'-diacetoxy-fluorenylidene-9'-hydrazono)-5-heptylidene-thiazolidone-4 exhibiting anti-influenza action against the influenza a and a-2 virus
UA6149A1 (en) * 1986-06-10 1994-12-29 Львівський Державний Медичний Інститут 2-(2',7'-diacetoxy-fluorenylidene-9'-hydrazono)-5-(n-nitrobenzylidene)-thiazolidone-4 exhibiting antiviral action against the influenza a and a-2 virus and vaccinia virus
US7341720B2 (en) * 2005-04-06 2008-03-11 Genzyme Corporation Targeting of glycoprotein therapeutics
EP2004649B1 (en) * 2006-03-24 2012-07-04 The Feinstein Institute for Medical Research Phenolic hydrazone macrophage migration inhibitory factor inhibitors
CN101830854A (en) * 2009-03-09 2010-09-15 中国科学院上海药物研究所 Substituted phenylhydrazones compounds, preparation method and application thereof
WO2011113060A2 (en) * 2010-03-12 2011-09-15 Trana Discovery, Inc. Antiviral compounds and methods of use thereof
CN104024849A (en) * 2011-08-12 2014-09-03 生命科技公司 Apparatuses, methods, computer program products, and kits for hi-throughput glycan analysis
CN105796545A (en) * 2016-05-25 2016-07-27 华中师范大学 Applications of hydrazone compound in preparing antifungal medicine
CN107987033A (en) * 2018-01-05 2018-05-04 湖南大学 The application of vanillic aldehyde and its isomers in NA inhibitor is prepared

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACT RN: "RN：1087696-44-3 等", 《STN ON THE WEB REGISTRY数据库》 *
DANIELLE CRISTINA ZIMMERMANN-FRANCO ETAL: "In vitro and in vivo anti-inflammatory properties of imine resveratrol analogues", 《BIOORGANIC & MEDICINAL CHEMISTRY (2018)》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115160180A (en) * 2022-06-22 2022-10-11 广东海洋大学 Green synthesis method of vanillin shrinkage 2, 4-dinitrophenylhydrazone

Also Published As

Publication number Publication date
CN110229081B (en) 2022-02-08

Similar Documents

Publication Publication Date Title
CN105622558B (en) Acyl hydrazone derivative of the ring containing benzofuran and preparation method and application
CN105693665B (en) Hydrazone derivative of the ring containing benzofuran and preparation method thereof and medical usage
CN108440468A (en) 2- (benzofuran -5- bases) phenol and its application as anticancer drug
CN105777664B (en) Carboxylate of 2 (2 benzyl hydrazono-) thiazole 5 and preparation method thereof and medical usage
CN108503604A (en) (4- alkyl -5- acyl group -2- thiazoles) hydazone derivative and its medical usage
CN107987033A (en) The application of vanillic aldehyde and its isomers in NA inhibitor is prepared
CN110229081A (en) 2,4- dinitrobenzene hydazone derivative and the preparation method and application thereof
CN105541859B (en) Dihydrofuran and chromanone derivatives and preparation method thereof and medical usage
CN107286133B (en) Application of -5 (the 4H)-thioketones imines of 3- aryl -1,2,4- triazole as NA inhibitor
CN108047160A (en) 2- (2- benzyls hydrazono-) -5- acyl groups thiazoles and its medical usage
CN105541591B (en) 1‑（The aryl phenyl of 4 hydroxyl 3）2 acetone and preparation method and application
CN108546254A (en) 5- (3- phenyl acryloyls) thiazole and the preparation method and application thereof
CN108530439A (en) Furoyl amine derivative and the preparation method and application thereof
CN105669589B (en) 2 (imino group of 5 acyl group thiazole 2) 4 thiazolinones and preparation method and application
CN110183349A (en) Oxalyl hydazone derivative and the preparation method and application thereof
CN109053607A (en) 4- (4- hydroxy phenyl methylene amino) -1,2,4- triazole -5- thioketones and its medical usage
CN107118176B (en) N-(5- benzyl thiazol-2-yl) morpholinyl amide and its medical usage
CN109053606A (en) 4- (4- hydroxy phenyl methylene amino) -1,2,4- triazole -5- thioketones and its application
CN107141267B (en) N- (5- acyl group thiazol-2-yl) amide and the preparation method and application thereof
CN111909082B (en) Pyridine hydrazone derivatives, and preparation method and application thereof
CN111100074B (en) Pyridazine hydrazone derivative and preparation method and application thereof
CN108863972A (en) Oxazole amide derivatives and the preparation method and application thereof
CN111909099B (en) Pyrimidine hydrazone derivatives, and preparation method and application thereof
CN109305979A (en) 4- dimethylaminobenzaldehyde is preparing the application in NA inhibitor
CN107011337B (en) N- [5- (1,2,4- triazol-1-yl) thiazol-2-yl] piperidyl amide and its medical usage

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant