CN109912566A - The synthesis of the novel fluorescence parent nucleus of one kind ring containing quinoline - Google Patents
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 230000015572 biosynthetic process Effects 0.000 title description 8
- 238000003786 synthesis reaction Methods 0.000 title description 8
- 239000000523 sample Substances 0.000 claims abstract description 10
- 238000010189 synthetic method Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000001514 detection method Methods 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 9
- 238000010898 silica gel chromatography Methods 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 229910018162 SeO2 Inorganic materials 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 3
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 3
- 150000002012 dioxanes Chemical class 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- 239000002024 ethyl acetate extract Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000003480 eluent Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 229960001866 silicon dioxide Drugs 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 6- (pyrrolidin-1-yl) quinoline -2- formaldehyde Chemical compound 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- QFDISQIDKZUABE-UHFFFAOYSA-N 1,1'-bipiperidine Chemical compound C1CCCCN1N1CCCCC1 QFDISQIDKZUABE-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The fluorescence parent nucleus of one kind ring containing quinoline, it has structure shown in following general formula I.The invention discloses the synthetic method of the fluorescence parent nucleus of a kind of novel ring containing quinoline and its applications in fluorescence probe design.
Description
Technical field
The invention belongs to biochemical field, more particularly to a kind of ring containing quinoline fluorescence parent nucleus synthesis and its in fluorescence
Application in probe design synthesis.
Background technique
Due to the needs of biology and clinic study, the exploitation of small-molecule fluorescent probe increasingly becomes the heat of research
Point.Fluorescence probe because have simple operations, high sensitivity and it is highly selective and be applied to detection metal ion and
Other small molecules.
Fluorescence probe is mainly made of recognition group, connector and fluorescence parent nucleus.Existing fluorescence probe exists glimmering mostly
Luminous intensity is weaker, excitation wavelength is smaller, light resistance is poor, the disadvantages of being difficult to apply in biological tissue.Therefore, it rationally designs, sieve
Select a kind of novel fluorogen for small-molecule fluorescent probe should being used to say that for biology, clinical medicine and Other subjects must
It wants.
Influence many because being known as of fluorescence probe intensity, such as suction, the electron supplying capacity of pH, concentration, substituent group.In phase
Under same environment, the present invention is transformed designed fluorescence parent nucleus by connecting different substituent groups, therefrom screens optimal
Structure provides theoretical foundation for the synthesis of subsequent probes.
Summary of the invention
The present invention relates to the synthesis of the fluorescence parent nucleus of one kind ring containing quinoline and the application in fluorescence probe design synthesis.
Technical scheme is as follows:
The derivative of one kind ring containing quinoline, chemical structural formula are as follows:
Wherein, R is selected from:
The synthetic method of the derivative of one kind ring containing quinoline, it is characterized in that it is made of the following steps:
Step 1 Weigh Compound II (5000mg, 29.07mmol) is added in 500mL round-bottomed flask, 6M hydrochloric acid (300mL)
Compound II is dissolved, 1h is stirred at room temperature, crotonaldehyde (7.2mL, 87.20mmol, 3eq) is added into bottle in 100 DEG C of oil baths
It is heated to reflux 2h, the reaction of TLC tracing detection is until compound II fully reacting.With the NaOH solution of saturation adjust reaction solution PH to
Neutrality, ethyl acetate extract three times, take organic phase, and anhydrous sodium sulfate is dry, and organic phase liquid is steamed using vacuum rotary evaporator
It is dry, using 200-300 mesh silica gel column chromatography separating purification crude product, finally obtain the solid of shape containing pale yellow powder i.e. compound
III (3685mg, yield 73.7%).
Step 2 weighs SeO2(400mg, 3.6mmol) is added in 100mL round-bottomed flask, with dioxanes: water (25mL:
It 2.5mL) is dissolved, 80 DEG C of stirring 30min, is added compound III (500mg, 2.25mmol), 80 DEG C of stirring 4h, TLC tracking
Detection reaction is until raw material, that is, compound III fully reacting.It is cooled to room temperature, diatomite filtering, methylene chloride repeatedly drenches on a small quantity
It washes, filtrate is evaporated with vacuum rotary evaporator, using 200-300 mesh silica gel column chromatography separating purification crude product, finally obtain
Yellow pellet-like solids, that is, compound IV (378mg, 75.6%).
Step 3 Weigh Compound IV (165mg, 0.699mmol) is added in 50mL round-bottomed flask, and 10mL toluene is by chemical combination
Object C dissolution, weighs palladium acetate (9.4mg, 0.042mmol, 0.06eq), cesium carbonate (273mg, 0.84mmol, 1.2eq), BINAP
(26.12mg, 0.042mmol, 0.06eq), different azacyclo-s are proportionally added into reaction solution, are heated to reflux 8h, TLC in 100 DEG C
Tracing detection reaction, entire reaction process are protected with argon gas.Reaction solution is used into suction filtered through kieselguhr, retains filtrate and is revolved again with vacuum
Turn evaporimeter to be evaporated, using 200-300 mesh silica gel column chromatography separating purification crude product, finally obtaining one kind has green glimmering to yellow
The faint yellow solid of light, i.e., the derivative of a kind of ring containing quinoline.
A kind of derivative containing quinoline that the present invention designs synthesis has stronger fluorescence, is being designed synthesized micromolecule
Fluorescence probe direction has very big potentiality.
Specific embodiment
The preparation of embodiment one: 6- (azetidine -1- base) quinoline -2- formaldehyde
Weigh Compound II (5000mg, 29.07mmol) is added in 500mL round-bottomed flask, and 6M hydrochloric acid (300mL) is by chemical combination
Object II dissolution, is stirred at room temperature 1h, and crotonaldehyde (7.2mL, 87.20mmol, 3eq) is added into bottle and heats back in 100 DEG C of oil baths
2h is flowed, the reaction of TLC tracing detection is until compound II fully reacting.Reaction solution PH is adjusted to neutrality with the NaOH solution of saturation,
Ethyl acetate extracts three times, takes organic phase, and anhydrous sodium sulfate is dry, and organic phase liquid is evaporated using vacuum rotary evaporator, is made
With 200-300 mesh silica gel column chromatography separating purification crude product, the solid of shape containing pale yellow powder i.e. compound III is finally obtained
(3685mg, yield 73.7%).
Weigh SeO2(400mg, 3.6mmol) is added in 100mL round-bottomed flask, will with dioxanes: water (25mL: 2.5mL)
It is dissolved, 80 DEG C of stirring 30min, is added compound III (500mg, 2.25mmol), 80 DEG C of stirring 4h, the reaction of TLC tracing detection
Until raw material, that is, compound III fully reacting.It is cooled to room temperature, diatomite filtering, methylene chloride repeatedly elutes on a small quantity, by filtrate
It is evaporated with vacuum rotary evaporator, using 200-300 mesh silica gel column chromatography separating purification crude product, it is solid to finally obtain yellow sheet
Body, that is, compound IV (378mg, 75.6%).
Weigh Compound IV (165mg, 0.699mmol) is added in 50mL round-bottomed flask, and 10mL toluene is molten by compound C
Solution, weighs palladium acetate (9.4mg, 0.042mmol, 0.06eq), cesium carbonate (273mg, 0.84mmol, 1.2eq), BINAP
(26.12mg, 0.042mmol, 0.06eq), azetidine (47.85 μ L, 0.961mmol, 1.375eq) are proportionally added into instead
It answers in liquid, 8h, the reaction of TLC tracing detection is heated to reflux in 100 DEG C, entire reaction process is protected with argon gas.Reaction solution is used
Suction filtered through kieselguhr is retained filtrate and is evaporated again with vacuum rotary evaporator, slightly produced using 200-300 mesh silica gel column chromatography separating purification
Object finally obtains the yellow solid of the fluorescence containing glassy yellow, i.e. 6- (azetidine -1- base) quinoline -2- formaldehyde (20.68mg).
Yield: 13.60%.1H NMR (600MHz, DMSO-d6) δ 9.99 (d, J=0.8Hz, 1H), 8.18 (d, J=8.5Hz, 1H),
7.99 (d, J=9.1Hz, 1H), 7.81 (d, J=8.5Hz, 1H), 7.16 (dd, J=9.1,2.6Hz, 1H), 6.69 (d, J=
2.5Hz, 1H), 4.04 (t, J=7.3Hz, 4H), 2.43-2.38 (m, 2H)
The preparation of embodiment two: 6- (pyrrolidin-1-yl) quinoline -2- formaldehyde
Preparation method reference implementation example one.Obtain yellow powder, yield: 28.19%.1H NMR (600MHz, DMSO-d6) δ
9.97 (s, 1H), 8.16 (d, J=8.5Hz, 1H), 7.99 (d, J=9.2Hz, 1H), 7.79 (d, J=8.5Hz, 1H), 7.40
(dd, J=9.3,2.7Hz, 1H), 6.82 (d, J=2.7Hz, 1H), 3.45-3.42 (m, 4H), 2.05-2.01 (m, 4H)
The preparation of embodiment three: 6- (piperidin-1-yl) quinoline -2- formaldehyde
Preparation method reference implementation example one.Obtain yellow powder, yield: 35.61%.1H NMR (600MHz, DMSO-d6) δ
10.01 (s, 1H), 8.23 (d, J=8.5Hz, 1H), 7.98 (d, J=9.4Hz, 1H), 7.83 (d, J=8.5Hz, 1H), 7.73
(dd, J=9.4,2.8Hz, 1H), 7.24 (d, J=2.8Hz, 1H), 3.44 (t, J=5.0Hz, 4H), 1.67-1.60 (m, J=
4.8Hz, 6H)
Example IV: the preparation of 6- (azepan -1- base) quinoline -2- formaldehyde
Preparation method reference implementation example one.Obtain pale yellow powder, yield: 23.65%.1H NMR (600MHz, DMSO-d6)
δ 9.97 (s, 1H), 8.15 (d, J=8.6Hz, 1H), 7.97 (d, J=9.4Hz, 1H), 7.78 (d, J=8.5Hz, 1H), 7.55
(dd, J=9.5,2.9Hz, 1H), 7.01 (d, J=2.9Hz, 1H), 3.65 (t, J=6.1Hz, 4H), 1.83-1.78 (m, 4H),
1.49 (p, J=2.7Hz, 4H)
The preparation of embodiment five: 6- (morpholine -1- base) quinoline -2- formaldehyde
Preparation method reference implementation example one.Obtain yellow powder, yield: 25.78%.1H NMR (600MHz, DMSO-d6) δ
10.03 (d, J=0.8Hz, 1H), 8.30-8.28 (m, 1H), 8.05-8.03 (m, 1H), 7.87 (d, J=8.5Hz, 1H), 7.78
(dd, J=9.4,2.8Hz, 1H), 7.30 (d, J=2.8Hz, 1H), 3.81-3.79 (m, 4H), 3.40-3.37 (m, 4H)
The preparation of embodiment six: 6- (piperidinyl piperidine -1- base) quinoline -2- formaldehyde
Preparation method reference implementation example one.Yellow powder is obtained, yield: 16.27%.1H NMR (600MHz,
Chloroform-d) δ 10.05 (s, 1H), 7.96 (dd, J=12.3,8.9Hz, 2H), 7.83 (dd, J=8.4,1.6Hz, 1H),
7.47 (dd, J=9.4,2.7Hz, 1H), 6.93 (d, J=2.6Hz, 1H), 3.94 (d, J=12.7Hz, 2H), 2.89-2.82
(m, 2H), 2.64 (s, 5H), 2.03 (d, J=12.0Hz, 2H), 1.70 (d, J=27.4Hz, 6H), 1.43 (s, 2H)
Claims (4)
1. the fluorescence parent nucleus of a kind of ring containing quinoline, it is characterised in that have structure shown in general formula I:
Wherein, R is selected from:
2. the preparation method of the novel fluorescence parent nucleus of one kind ring containing quinoline described in claim 1, it is characterized in that it is by following step
Rapid composition:
Step 1 Weigh Compound II (5000mg, 29.07mmol) is added in 500mL round-bottomed flask, and 6M hydrochloric acid (300mL) will be changed
Object II dissolution is closed, 1h is stirred at room temperature, crotonaldehyde (7.2mL, 87.20mmol, 3eq) is added into bottle and is heated in 100 DEG C of oil baths
Flow back 2h, and the reaction of TLC tracing detection is until compound II fully reacting.Reaction solution PH is adjusted into the NaOH solution of saturation
Property, ethyl acetate extracts three times, takes organic phase, and anhydrous sodium sulfate is dry, organic phase liquid is evaporated using vacuum rotary evaporator,
Using 200-300 mesh silica gel column chromatography separating purification crude product, the solid of shape containing pale yellow powder i.e. compound III is finally obtained
(3685mg, yield 73.7%).
Step 2 weighs SeO2(400mg, 3.6mmol) is added in 100mL round-bottomed flask, will with dioxanes: water (25mL: 2.5mL)
It is dissolved, 80 DEG C of stirring 30min, is added compound III (500mg, 2.25mmol), 80 DEG C of stirring 4h, the reaction of TLC tracing detection
Until raw material, that is, compound III fully reacting.It is cooled to room temperature, diatomite filtering, methylene chloride repeatedly elutes on a small quantity, by filtrate
It is evaporated with vacuum rotary evaporator, using 200-300 mesh silica gel column chromatography separating purification crude product, it is solid to finally obtain yellow sheet
Body, that is, compound IV (378mg, 75.6%).
Step 3 Weigh Compound IV (165mg, 0.699mmol) is added in 50mL round-bottomed flask, and 10mL toluene is molten by compound C
Solution, weighs palladium acetate (9.4mg, 0.042mmol, 0.06eq), cesium carbonate (273mg, 0.84mmol, 1.2eq), BINAP
(26.12mg, 0.042mmol, 0.06eq), different azacyclo-s are proportionally added into reaction solution, are heated to reflux 8h, TLC in 100 DEG C
Tracing detection reaction, entire reaction process are protected with argon gas.Reaction solution is used into suction filtered through kieselguhr, retains filtrate and is revolved again with vacuum
Turn evaporimeter to be evaporated, using 200-300 mesh silica gel column chromatography separating purification crude product, finally obtaining one kind has green glimmering to yellow
The faint yellow solid of light, i.e., the derivative of a kind of ring containing quinoline.
It is using 200-300 mesh silicagel column, eluant, eluent 3. synthetic method according to claim 2 chromatographs described in step
For a certain proportion of anhydrous ethyl acetate and petroleum ether.
4. the synthetic method of the novel fluorescence parent nucleus of one kind ring containing quinoline described in claim 1 is closed with the design in fluorescence probe
Application in.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113880821A (en) * | 2021-10-29 | 2022-01-04 | 南京碳硅人工智能生物医药技术研究院有限公司 | Design and synthesis method of fluorescent probe for imaging epileptic intracerebral hypochlorous acid characteristics by two-photon fluorescent probe |
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|---|---|---|---|---|
| JP2007055956A (en) * | 2005-08-26 | 2007-03-08 | Tokyo Univ Of Pharmacy & Life Science | New quinoline compound as fluorescent labeling reagent and hydrophobic site-detecting reagent |
| EP3239143A2 (en) * | 2014-12-24 | 2017-11-01 | LG Chem, Ltd. | Biaryl derivative as gpr120 agonist |
| CN107417609A (en) * | 2017-06-23 | 2017-12-01 | 南京大学 | The synthesis of the fluorescence parent nucleus of a kind of new ring containing quinoline |
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- 2017-12-12 CN CN201711370139.5A patent/CN109912566A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007055956A (en) * | 2005-08-26 | 2007-03-08 | Tokyo Univ Of Pharmacy & Life Science | New quinoline compound as fluorescent labeling reagent and hydrophobic site-detecting reagent |
| EP3239143A2 (en) * | 2014-12-24 | 2017-11-01 | LG Chem, Ltd. | Biaryl derivative as gpr120 agonist |
| CN107417609A (en) * | 2017-06-23 | 2017-12-01 | 南京大学 | The synthesis of the fluorescence parent nucleus of a kind of new ring containing quinoline |
Non-Patent Citations (1)
| Title |
|---|
| CA: "1266846-72-3/RN OR 1266853-33-1/RN OR 1266870-87-4/RN", 《STN ON THE WEB》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113880821A (en) * | 2021-10-29 | 2022-01-04 | 南京碳硅人工智能生物医药技术研究院有限公司 | Design and synthesis method of fluorescent probe for imaging epileptic intracerebral hypochlorous acid characteristics by two-photon fluorescent probe |
| CN113880821B (en) * | 2021-10-29 | 2024-03-12 | 南京碳硅人工智能生物医药技术研究院有限公司 | Fluorescent probe design for epileptic intracerebral hypochlorous acid characteristic imaging by two-photon fluorescent probe and synthetic method thereof |
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Application publication date: 20190621 |