CN110183349A - Oxalyl hydazone derivative and the preparation method and application thereof - Google Patents
Oxalyl hydazone derivative and the preparation method and application thereof Download PDFInfo
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- CN110183349A CN110183349A CN201910499606.7A CN201910499606A CN110183349A CN 110183349 A CN110183349 A CN 110183349A CN 201910499606 A CN201910499606 A CN 201910499606A CN 110183349 A CN110183349 A CN 110183349A
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A61P31/14—Antivirals for RNA viruses
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- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/16—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of hydrazones
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- 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
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Abstract
The present invention relates to oxalyl 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
Technical field
The present invention relates to a kind of noval chemical compound, preparation method and applications, specifically oxalyl hydazone derivative, its preparation side
Method and its in the application for preparing influenza virus neuraminidase inhibitor.
Background technique
2007, Li et al. [Brazilian Journal of Chemical Engineering, 2007,24 (4): 471-
475] it describes and adipyl hydazone derivative is prepared for by solvent-free microwave auxiliary law with adipic dihydrazide and aromatic aldehyde.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of oxalyl hydazone derivative, preparation method, pharmaceutical composition and
Purposes.
To solve technical problem of the invention, the invention provides the following technical scheme:
There is provided a kind of oxalyl hydazone derivative and its medicines as shown in structural formula I for the first aspect of technical solution of the present invention
Acceptable salt on:
Wherein, R 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: two (4- hydroxy benzaldehyde) oxalyl hydrazones, two (3- methoxyl group -4- hydroxyls
Benzaldehyde) oxalyl hydrazone, two (3,4- 4-dihydroxy benzaldehyde) oxalyl hydrazones or two (2,4- 4-dihydroxy benzaldehyde) oxalyl hydrazones.
There is provided the preparation methods of oxalyl hydazone derivative for the second aspect of technical solution of the present invention, it is characterised in that it
Preparation reaction it is as follows:
Wherein, R 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, which contains the oxalyl hydazone derivative of the invention and its pharmaceutically of therapeutically effective amount
Acceptable salt, and optional contain pharmaceutical carrier.Wherein the pharmaceutical carrier refers to the common pharmaceutical carrier of pharmaceutical field；
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, and being made makes suitable for human or animal
Any dosage form.The content of the compounds of this invention and its pharmaceutically acceptable salt in its pharmaceutical composition is usually
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 oxalyl hydazone derivative of the present invention and its can pharmaceutically connect
Application of the salt and third aspect described pharmaceutical composition received in terms of preparing influenza virus neuraminidase inhibitor.
Advantageous effects:
Oxalyl hydazone derivative of the invention is a kind of compound with influenza neuraminidase inhibitory activity.
Specific embodiment
Following embodiment is intended to illustrate invention rather than limitation of the invention further.
Embodiment 1
The preparation of two (4- hydroxy benzaldehyde) oxalyl hydrazones (I a)
(1) preparation of oxalyl dihydrazide
6.0mmol diethyl oxalate and 80% hydrazine hydrate of 24.0mmol are placed in 16mL ethyl alcohol, are reacted 3h, will be reacted
Mixture is cooled to room temperature, then is filtered, and filter cake passes through petroleum ether and ethanol washing, dry oxalyl dihydrazide, white solid,
M.p.240~241 DEG C, yield 90.5%.
The preparation of (2) two (4- hydroxy benzaldehyde) oxalyl hydrazones (I a)
1.0mmol oxalyl dihydrazide, 2.1mmol 4- hydroxy benzaldehyde and 2 drop acetic acid are suspended in 16mL ethyl alcohol, and flow back 4h,
TLC monitoring reaction.Reaction solution is cooled to room temperature, and is filtered, with petroleum ether and ethanol washing filter cake, dry two (4- hydroxy benzenes first
Aldehyde) oxalyl hydrazone (I a), faint yellow solid, m.p. > 280 DEG C, yield 96.9%；1H NMR (400MHz, DMSO-d6) δ: 12.07
(s, 2H, 2 × NH), 10.00 (s, 2H, 2 × OH), 8.49 (s, 2H, 2 × CH), 7.54 (d, J=8.0Hz, 4H, C6H4), 6.84
(d, J=8.0Hz, 4H, C6H4)；13C NMR (100MHz, DMSO-d6) δ: 159.86,155.99,151.25,129.26,
124.84,115.77.
Embodiment 2
The preparation of two (2,4- 4-dihydroxy benzaldehyde) oxalyl hydrazones (I b)
According to the method preparation of (2) in embodiment 1,1.0mmol oxalyl dihydrazide and 2.1mmol 2,4- 4-dihydroxy benzaldehyde
4h is reacted, two (2,4- 4-dihydroxy benzaldehyde) oxalyl hydrazones (I b), yellow solid, m.p. > 280 DEG C, yield 94.7% are obtained；1HNMR (400MHz, DMSO-d6) δ: 12.42 (s, 2H, 2 × OH), 11.21 (s, 2H, 2 × NH), 10.04 (s, 2H, 2 × OH),
8.65 (s, 2H, CH), 7.30 (d, J=8.5Hz, 2H, C6H3), 6.36 (d, J=8.5Hz, 2H, C6H3), 6.31 (s, 2H,
C6H3)；13C NMR (100MHz, DMSO-d6) δ: 161.26,159.70,155.54,151.92,131.47,110.40,
107.97,102.64.
Embodiment 3
The preparation of two (Vanillin) oxalyl hydrazones (I c)
According to the method preparation of (2) in embodiment 1,1.0mmol oxalyl dihydrazide and 2.1mmol 3- methoxyl group -4- hydroxy benzenes
Formaldehyde reacts 4h, obtains two (Vanillin) oxalyl hydrazones (I c), white solid, m.p. > 280 DEG C, yield
95.8%；1H NMR (400MHz, DMSO-d6) δ: 12.08 (s, 2H, 2 × NH), 9.64 (s, 2H, 2 × OH), 8.49 (s, 2H, 2
× CH), 7.28 (s, 2H, C6H3), 7.09 (d, J=8.2Hz, 2H, C6H3), 6.85 (d, J=8.2Hz, 2H, C6H3), 3.83 (s,
6H, CH3)；13C NMR (100MHz, DMSO-d6) δ: 156.01,151.62,149.51,148.05,125.23,122.61,
115.53 109.39,55.62.
Embodiment 4
The preparation of two (3,4- 4-dihydroxy benzaldehyde) oxalyl hydrazones (I d)
According to the method preparation of (2) in embodiment 1,1.0mmol oxalyl dihydrazide and 2.1mmol 3,4- 4-dihydroxy benzaldehyde
4h is reacted, two (3,4- 4-dihydroxy benzaldehyde) oxalyl hydrazones (I d), gray solid, m.p. > 280 DEG C, yield 95.7% are obtained；1H
NMR (400MHz, DMSO-d6) δ: 12.03 (s, 2H, 2 × NH), 9.47 (s, 2H, 2 × OH), 9.30 (s, 2H, 2 × OH), 8.40
(s, 2H, 2 × CH), 7.23 (s, 2H, C6H3), 6.92 (d, J=8.1Hz, 2H, C6H3), 6.79 (d, J=8.1Hz, 2H, C6H3)
；13C NMR (100MHz, DMSO-d6) δ: 155.98,151.46,148.48,145.76,125.31,121.10,115.64,
112.91。
Embodiment 5
The resisiting influenza virus neuraminidase activity of oxalyl 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 (pH 6.5),
Fluorogenic substrate MUNANA is added and starts reaction system, 37 DEG C are incubated for after forty minutes, and reaction terminating liquid is added to terminate reaction.In excitation wave
Under the Parameter Conditions that long 360nm and launch wavelength are 450nm, fluorescence intensity level is measured.The fluorescence intensity of reaction system can be anti-
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 oxalyl hydazone derivative of table to neuraminidase H1N150
| Compound | R | Inhibiting rate (%) | IC50(μg/mL) |
| Ⅰa | 4-OH | 89.77±1.64 | 6.79±0.98 |
| Ⅰb | 2,4-(OH)2 | 81.10±1.02 | 13.84±1.43 |
| Ⅰc | 4-OH-3-OCH3 | 88.53±0.90 | 8.46±0.36 |
| Ⅰd | 3,4-(OH)2 | 34.27±0.36 | - |
Oxalyl hydazone derivative has resisiting influenza virus neuraminidase activity, can be used for preparing influenza virus neuraminidase
Enzyme inhibitor.
Claims (5)
1. oxalyl hydazone derivative and its pharmaceutically acceptable salt shown in a kind of chemical structural formula I:
Wherein, R 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. a kind of oxalyl hydazone derivative and its pharmaceutically acceptable salt, are selected from following compounds:
Two (4- hydroxy benzaldehyde) oxalyl hydrazones,
Two (Vanillin) oxalyl hydrazones,
Two (3,4- 4-dihydroxy benzaldehyde) oxalyl hydrazones or
Two (2,4- 4-dihydroxy benzaldehyde) oxalyl hydrazones.
3. the preparation method of oxalyl hydazone derivative described in claim 1, which is characterized in that its preparation reaction is as follows:
In formula, the definition of R is as described in claim 1.
4. oxalyl hydazone derivative of any of claims 1 or 2 and its pharmaceutically acceptable salt are in preparation influenza virus mind
Through the application in propylhomoserin enzyme inhibitor.
5. available carrier at least one of a kind of pharmaceutical composition, including claims 1 or 2 compound and pharmaceutics.
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