CN110256467A - A kind of tracer specially fluorescence probe of azoles amine antibiotic and application - Google Patents
A kind of tracer specially fluorescence probe of azoles amine antibiotic and application Download PDFInfo
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- CN110256467A CN110256467A CN201910642890.9A CN201910642890A CN110256467A CN 110256467 A CN110256467 A CN 110256467A CN 201910642890 A CN201910642890 A CN 201910642890A CN 110256467 A CN110256467 A CN 110256467A
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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Abstract
The present invention relates to a kind of tracers specially fluorescence probe of azoles amine antibiotic and application, belong to field of fine chemical.The dehydration under O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester effect of the fluorescence probe of this kind of tracer specially azoles amine antibiotic forms ester bond and connect fluorescent chromophore with specially azoles amine, being capable of tracer specially mechanism of the azoles amine in human body cell by fluorescent microscopic imaging.Microenvironment locating for research specially metabolic process and its target point protein of the azoles amine in human body cell has great importance for the research and development of subsequent new drug.
Description
Technical field
The present invention relates to a kind of tracers specially fluorescence probe of azoles amine antibiotic and application, belong to field of fine chemical.
Background technique
Oxazolidinones antimicrobial is the fully synthetic antimicrobial of a kind of new chemical.Such drug has one in chemical structure
Oxazolidinedione parent nucleus has completely new antibacterial mechanisms, to the Grain-positive ball of gram-positive cocci, especially multidrug resistant
Bacterium has stronger antibacterial activity, and crossing drug resistant phenomenon is not present with other drugs.Linezolid and specially azoles amine are two kinds of masters
The oxazolidinones antimicrobial wanted, compared with Linezolid, specially 1) azoles amine has the advantage that specially azoles amine half-life period is benefit
How twice of azoles amine, can reduce the generation of drug resistance, reduce drug side-effect, and improve the compliance of patient.2) preferably
Internal bactericidal activity.3) lower drug resistance.4) the plasma concentration individual difference of specially azoles amine is small, therefore it is to different patients'
Validity and safety are more consistent.5) drug drug interaction is less.Specially azoles amine will not in the presence of tyrasamine and pseudoephedrine
Cause heart rate very fast or blood pressure increases, and Linezolid then has this effect.6) long-term administration safety is more preferable.Specially azoles amine is bad
It reacts incidence and thrombopenia incidence is low compared with Linezolid.
Specially azoles amine is second generation oxazolidinones antimicrobial, is a kind of protein inhibitor, by inhibiting bacterioprotein
The synthesis of matter is to play antibacterial action.Specially azoles amine shows excellent performance in antibiosis, while generating bad anti-
Should be very low, therefore, the research specially Antibacterial Mechanism of azoles amine is to its metabolic process in human body cell for subsequent related new drug
Research and development have great importance.
Summary of the invention
To solve problems of the prior art, the present invention provides the fluorescence probe of a kind of tracer specially azoles amine antibiotic
And fluorescent chromophore is connect by application, the compound by ester bond with specially azoles amine, it being capable of tracer spy by fluorescent microscopic imaging
Mechanism of the ground azoles amine in human body cell, to study the specially Antibacterial Mechanism of azoles amine and its metabolism in human body cell
Journey provides a kind of fluorescent visual tool.
The technical solution adopted by the present invention are as follows: a kind of tracer specially fluorescence probe of azoles amine antibiotic and, the knot of the probe
Structure general formula is as follows:
In general formula, R1And R2It can be different groups；
R3WithR3And R4It can be different groups；
Wherein:The integer of n=0-18, m=0-18's is whole
Number, n1The integer of=0-11, n2The integer of=1-8, the integer of e=0-18, n3The integer of=0-18, n4The integer of=1-18；X-
For anion, the anion is BF4 -、Cl-、Br-、I-、NO3 -、SO4 2-、ClO4 -、CH3COO-、CH3SO3 -Or CF3SO3 -；It is describedThe positively charged sum of institute is equal to anion X-The negatively charged sum of institute, R5And R6It can be different groups.
A kind of tracer specially fluorescence probe of azoles amine antibiotic and the preparation method of application, which is characterized in that compound A
Dehydration forms ester bond synthesis compound C under O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester effect with compound B.
Wherein, R1、R2、R3、R4Definition with Y is the same as the definition in general structure.
One kind tracer specially application of the fluorescence probe of azoles amine antibiotic and application, the fluorescence probe are applied to tracer
Specially azoles amine antibiotic.
The beneficial effects of the present invention are: the present invention provides a kind of tracer specially fluorescence probe of azoles amine antibiotic and application,
Compound dehydration under the effect of O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester formed ester bond by fluorescent chromophore with specially
The connection of azoles amine, being capable of tracer specially effect of the azoles amine in human body cell by the fluorescence developing of sulfonic acid rhodamine fluorescent chromophore
Mechanism and process.A kind of fluorescent visual is provided to study the specially Antibacterial Mechanism of azoles amine and its metabolic process in human body cell
Chemical industry tool, has great importance for the research and development of subsequent dependency structure new drug, while being also specially azoles amine new drug development process
The adverse reaction of middle determining new drug provides a kind of new judgment method.
Specific embodiment
The present invention is illustrated with following instance but not limited to this, wherein unless otherwise indicated, all numbers and hundred
Score is by weight.
Specific embodiments of the present invention are described in detail below in conjunction with technical solution.
Embodiment 1
Weigh Compound A1Solvent 1 is added in reaction flask in (1.01g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 2
Weigh Compound A2Solvent 1 is added in reaction flask in (1.18g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 3
Weigh Compound A3Solvent 1 is added in reaction flask in (1.12g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 4
Weigh Compound A4Solvent 1 is added in reaction flask in (1.23g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 5
Weigh Compound A5Solvent 1 is added in reaction flask in (1.07g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 6
Weigh Compound A6Solvent 1 is added in reaction flask in (1.49g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 7
Synthetic method is referring to embodiment 6.
Embodiment 8
Weigh Compound A8Solvent 1 is added in reaction flask in (1.13g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 9
Weigh Compound A9Solvent 1 is added in reaction flask in (1.19g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 10
Weigh Compound A10Solvent 1 is added in reaction flask in (1.36g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 11
Synthetic method is referring to embodiment 11.
Embodiment 12
Weigh Compound A12Solvent 1 is added in reaction flask in (1.25g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 13
Weigh Compound A13Solvent 1 is added in reaction flask in (1.4g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 14
Synthetic method is referring to embodiment 13.
Embodiment 15
Weigh Compound A15Solvent 1 is added in reaction flask in (1.41g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 16
Weigh Compound A16Solvent 1 is added in reaction flask in (1.21g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 17
Synthetic method is the same as embodiment 16.
Embodiment 18
Weigh Compound A18Solvent 1 is added in reaction flask in (1.61g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Embodiment 19
Weigh Compound A19Solvent 1 is added in reaction flask in (1.72g, 2mmol), and 2- dichloroethanes is sufficiently stirred, will be warm
Degree is down to -5 DEG C hereinafter, O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester (1.14g, 3mmol) is added, and stirs under room temperature
40min, then reaction temperature is down to -5 DEG C hereinafter, being slowly added to the N of compound B (0.93g, 2.5mmol), N- into reaction solution
Dimethyl formamide solution adds the triethylamine of catalytic amount, and normal-temperature reaction 5 hours, silica gel plate monitored extent of reaction, had reacted
Quan Hou, cooling, decompression steam solvent, and crude product is purified through pillar layer separation.Product structure is identified by HRMS.
Claims (3)
1. the fluorescence probe of a kind of tracer specially azoles amine antibiotic, which is characterized in that the general structure of the probe is as follows:
In general formula, R1, R1And R2It can be different groups；
R3WithR3And R4It can be different groups；
Wherein: R5,The integer of n=0-18, the integer of m=0-18, n1
The integer of=0-11, n2The integer of=1-8, the integer of e=0-18, n3The integer of=0-18, n4The integer of=1-18；X-For yin
Ion, the anion are BF4 -、Cl-、Br-、I-、NO3 -、SO4 2-、ClO4 -、CH3COO-、CH3SO3 -Or CF3SO3 -；It is describedThe positively charged sum of institute is equal to anion X-The negatively charged sum of institute, R5And R6It can be different groups.
2. the preparation method of the tracer specially fluorescence probe of azoles amine antibiotic according to claim 1, which is characterized in that chemical combination
Object A and compound B dehydration under O- benzotriazole-tetramethylurea hexafluorophosphoric acid ester effect forms ester bond synthesis compound C；
Wherein, R1、R2、R3、R4Definition with Y is the same as the definition in general structure.
3. the application of the tracer specially fluorescence probe of azoles amine antibiotic according to claim 1, it is characterised in that: the fluorescence
Probe application is in tracer specially azoles amine antibiotic.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111458430A (en) * | 2020-04-11 | 2020-07-28 | 昆明和合医学检验所有限公司 | Liquid chromatography tandem mass spectrometry quantitative detection method for concentration of drug-resistant bacteria infection resisting drug |
| CN111533761A (en) * | 2020-05-24 | 2020-08-14 | 大连理工大学 | Ratio type pH probe with organelle or protein targeting function and application thereof |
| CN111533761B (en) * | 2020-05-24 | 2021-09-21 | 大连理工大学 | Ratio type pH probe with organelle or protein targeting function and application thereof |
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