CN118373839A - Preparation of seven-membered bopyin heterocyclic compound and application of seven-membered bopyin heterocyclic compound in detection of viscosity in organic solution - Google Patents
Preparation of seven-membered bopyin heterocyclic compound and application of seven-membered bopyin heterocyclic compound in detection of viscosity in organic solution Download PDFInfo
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 16
- 238000001514 detection method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title abstract description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical compound COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 84
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229940125904 compound 1 Drugs 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 7
- 229940125782 compound 2 Drugs 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000002390 rotary evaporation Methods 0.000 claims description 2
- 238000010898 silica gel chromatography Methods 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- RUKJCCIJLIMGEP-ONEGZZNKSA-N 4-dimethylaminocinnamaldehyde Chemical compound CN(C)C1=CC=C(\C=C\C=O)C=C1 RUKJCCIJLIMGEP-ONEGZZNKSA-N 0.000 abstract description 7
- 239000000243 solution Substances 0.000 abstract description 7
- 238000000746 purification Methods 0.000 abstract description 6
- 239000011259 mixed solution Substances 0.000 abstract description 3
- 238000012544 monitoring process Methods 0.000 abstract description 3
- 230000008859 change Effects 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- ULUNQYODBKLBOE-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)-1h-pyrrole Chemical compound C1=CNC(C=2NC=CC=2)=C1 ULUNQYODBKLBOE-UHFFFAOYSA-N 0.000 abstract 1
- 238000000862 absorption spectrum Methods 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000000295 emission spectrum Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 20
- 239000000203 mixture Substances 0.000 description 8
- 239000012452 mother liquor Substances 0.000 description 8
- 238000002189 fluorescence spectrum Methods 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- MCGROFKAAXXTBN-VIZOYTHASA-N 3,5-dihydroxy-N-[(E)-(4-hydroxy-3-nitrophenyl)methylideneamino]benzamide Chemical compound C1=CC(=C(C=C1/C=N/NC(=O)C2=CC(=CC(=C2)O)O)[N+](=O)[O-])O MCGROFKAAXXTBN-VIZOYTHASA-N 0.000 description 5
- -1 boron dipyrrole compound Chemical class 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011897 real-time detection Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses a preparation method of a seven-membered bopyin heterocyclic compound and application thereof in detecting viscosity in an organic solution, wherein the heterocyclic compound has the following structural formula: . Wherein, the substituent R 1 is any one selected from hydrogen, methoxy, bromine and cyano. The dye is prepared from para-substituted derivative of hepta-fluoro-boron dipyrrole and p-dimethylamino cinnamaldehyde serving as raw materials through catalysis and condensation of piperidine, acetic acid and phosphorus oxychloride, and has the advantages of simple synthesis method, convenient separation and purification and high yield. The introduction of different substituents can lead the absorption and emission spectrum of the molecule to be red-shifted, and the structure of the molecule can be used for monitoring the change condition of viscosity in the mixed solution.
Description
Technical Field
The invention relates to a seven-membered bopyin heterocyclic compound, in particular to a seven-membered bopyin heterocyclic compound and viscosity application thereof.
Background
Viscosity is a key parameter of the microenvironment and plays an important role in the organism. However, high viscosity values are often associated with cardiovascular disease, diabetes, and tumor-like serious diseases, and therefore, accurate detection of viscosity is of great importance for better understanding of the pathology of the associated disease.
Methods and instruments for detecting viscosity that are currently being developed and utilized are capillary viscometers, falling ball viscometers, rotational viscometers, and the like. The capillary viscometer has simple principle, low working efficiency and larger detection error. The rotary viscometer has the advantages of quick, convenient and high accuracy in measurement, but the method has the advantages of more hardware equipment, complex structure and high price, and limits practical application. In summary, the above methods are not suitable for real-time detection of small samples or local viscosity, but the method using fluorescent probes can effectively avoid these defects, and can perform tissue or intracellular imaging due to their higher spatial resolution and temporal resolution. Therefore, the development of novel and efficient viscosity detection means for diagnosis and pathology screening of related diseases is of great value.
In view of the above problems, the invention provides a fluorescent probe of a seven-membered bopyin heterocyclic compound, which can be used for viscosity detection in mixed solution, viscosity change monitoring in polymerization process, viscosity measurement in cells or mitochondria, and the like due to long wavelength emission in the near infrared range. And has the advantages of easy detection, sensitive reaction, wide detection range, etc.
Disclosure of Invention
The invention mainly aims to provide a seven-membered bopyin heterocyclic compound and viscosity application thereof. The technical scheme of the invention is as follows:
a seven-membered bopyin heterocyclic compound and viscosity application thereof, wherein the chemical structural formula of the compound is as follows:
；
The substituent R is any one selected from hydrogen, methoxy, bromine and cyano. The chemical structural formula of the compound is as follows:
any one of the following.
A synthetic method for synthesizing the seven-membered bopyin heterocyclic compound, which comprises the following synthetic routes:
；
The method comprises the following steps:
(1) Adding a compound 1, a compound 2 and toluene into a reaction bottle at room temperature, performing ultrasonic dissolution, adding piperidine, and heating to obtain a reaction solution;
(2) And (3) performing rotary evaporation on the reaction liquid in the step (1), and separating by silica gel column chromatography to obtain a product Y. Compound 1 is a hepta-fluoro-boron dipyrrole derivative, and compound 2 is p-dimethylamino-cinnamic aldehyde; the feeding molar ratio of the compound 1 to the compound 2 is 1:1-2.
(3) The feeding sequence of the step (1) is compound 1, compound 2, toluene and piperidine; the feeding ratio of the compound 1 to the piperidine is 1:0.3-1.
The heating temperature in the step (1) is 20-100 ℃, and the heating time is 2-5 hours.
The invention has the following beneficial effects:
(1) The compound has certain response to the viscosity, the fluorescence of the compound is weak, but with the increase of the viscosity, the fluorescence is gradually enhanced, the maximum fluorescence of the viscosity is enhanced by 0.2-2.5 times, and the imaging contrast of viscosity monitoring is improved.
(2) The seven-membered bopyin heterocyclic compound viscosity probe disclosed by the invention is simple in preparation method, and the synthesized viscosity probe is sensitive to viscosity response in a DMF and glycerol mixed solution.
(3) Compared with other viscosity probes, the viscosity probe has the maximum fluorescence emission of one compound of about 820 nm.
(4) The method has the advantages of simpler synthesis steps, milder reaction temperature, small operation difficulty, quick reaction time which is not more than 5 hours at most, relatively higher yield and simple and convenient post-treatment and purification.
Drawings
FIG. 1 is a hydrogen spectrum of compound Y-1 obtained in example 1.
FIG. 2 is a hydrogen spectrum of the compound Y-2 obtained in example 3.
FIG. 3 is a hydrogen spectrum of compound Y-3 obtained in example 4.
FIG. 4 is a hydrogen spectrum of compound Y-4 obtained in example 5.
FIG. 5 is a graph showing fluorescence spectra of the compound Y-1 obtained in example 1 in DMF-glycerol mixtures of different proportions.
FIG. 6 is a linear relationship between the fluorescence intensity log I 807nm and log eta of the compound Y-1 obtained in example 1.
FIG. 7 is a graph showing fluorescence spectra of the compound Y-2 obtained in example 2 in DMF-glycerol mixtures of different proportions.
FIG. 8 is a linear relationship between the fluorescence intensity log I 800nm and log eta of the compound Y-2 obtained in example 2.
FIG. 9 is a graph showing fluorescence spectra of the compound Y-3 obtained in example 3 in DMF-glycerol mixtures of different proportions.
FIG. 10 is a linear relationship between the fluorescence intensity log I 815nm and log eta of the compound Y-3 obtained in example 3.
FIG. 11 is a graph showing fluorescence spectra of the compound Y-4 obtained in example 4 in DMF-glycerol mixtures of different proportions.
FIG. 12 is a linear relationship between the fluorescence intensity log I 820nm and log eta of the compound Y-4 obtained in example 4.
Detailed Description
The present invention will be further illustrated by the following examples, but the scope of the invention is not limited to the examples.
Example 1
Seven-membered boron dipyrrole compound (298 mg,1 mmol) of compound 1, 4-dimethylamino cinnamaldehyde (175 mg,1 mmol) was weighed, dissolved in 20mL toluene, piperidine (59. Mu.L, 0.3 mmol) was added thereto, heated and stirred for 5 hours at 100℃for complete reaction, the reaction was distilled off in a rotary manner, and after purification by column chromatography, purplish black solid Y-1 (218.4 mg) was obtained in 48% yield.
Y1
Example 2
Weighing compound 1 seven-membered boron dipyrrole fluoride compound (298 mg,1 mmol), dissolving 4-dimethylamino cinnamaldehyde (175 mg,1 mmol) in 20mL toluene, adding piperidine (59 mu L,0.6 mmol), heating at 100deg.C, stirring for 5 hr to react completely, rotary steaming the reactant, purifying by column chromatography to obtain purple-black solid Y-1 (273.1 mg), and increasing yield by 1 time relative to example 1 by 60%, and increasing yield by 12%
Y-1
Example 3
Seven-membered boron dipyrrole compound (328 mg,1 mmol), 4-dimethylamino cinnamaldehyde (210 mg,1.2 mmol), piperidine (99. Mu.L, 1 mmol) were weighed out, heated and stirred at 100℃for 3 hours to complete the reaction, the reaction was distilled off in a rotary manner, and after purification by column chromatography, purple-black solid Y-1 (203.7 mg) was obtained in 42% yield.
Y-2
Example 4
Seven-membered boron dipyrrole compound (377 mg,1 mmol), 4-dimethylamino cinnamaldehyde (210 mg,1.2 mmol), piperidine (59. Mu.L, 0.6 mmol) were weighed out, heated and stirred at 100deg.C for 3 hours to complete the reaction, the reaction was distilled off in a rotary manner, and after column chromatography purification, purple black solid Y-1 (224.3 mg) was obtained in 42% yield.
Y-3
Example 5
Seven-membered boron dipyrrole compound (323 mg,1 mmol), 4-dimethylamino cinnamaldehyde (210 mg,1.2 mmol), piperidine (99. Mu.L, 1 mmol) were weighed out, heated and stirred at 100℃for 3 hours to complete the reaction, the reaction was distilled off in a rotary manner, and after purification by column chromatography, purple-black solid Y-1 (190 mg) was obtained in 40% yield.
Y-4
Example 6 response of Compound Y-1 to viscosity
Weighing a compound Y-1 (4.55 mg,0.01 mmol), dissolving 1mL of DMF to prepare 0.01mol/L mother liquor, dissolving 10 mu L of mother liquor into 3mL of a mixture of DMF and glycerin with different viscosities respectively to prepare 33.3 mu mol/L to-be-measured solution, wherein (DMF: glycerin=7:3=2.1 mL:0.9mL, viscosity is 4.22 mPas), (DMF: glycerin=6:4=1.8 mL:1.2mL, viscosity is 7.36 mPas) (DMF: glycerin=5:5=1.5 mL:1.5mL, viscosity is 14.2 mPas), (DMF: glycerin=4:6=1.2 mL:1.8mL, viscosity is 19.9 mPas), (DMF: glycerin=3:7=0.9 mL:2.1mL, viscosity is 64.6 mPas), (DMF: glycerin=2:8=0.6:2.127:4=1.8 mL, and (DMF: 5:5=1.5 mL:1.5mL, 37 mL) and obtaining a linear relation between the fluorescent intensities and the fluorescent intensities obtained by respectively, and performing linear measurement in the figure, wherein the linear relation is that the linear relation is shown in fig. 25.25 mL, wherein the fluorescent intensities are obtained. Y-1 itself is weak in fluorescence, but as the viscosity increases, the fluorescence intensity gradually increases. The viscosity coefficient was 4.73 and the maximum fluorescence enhancement to viscosity was 1.2 times.
Example 7 response of Compound Y-2 to viscosity
Weighing compound Y-2 (4.85 mg,0.01 mmol), dissolving 1mL of DMF to prepare 0.01mol/L mother liquor, then dissolving 10 mu L of mother liquor into 3mL of a mixture of DMF and glycerin with different viscosities respectively to prepare 33.3 mu mol/L of to-be-measured solution, wherein (DMF: glycerin=7:3=2.1 mL:0.9mL, viscosity is 4.22 mPas), (DMF: glycerin=6:4=1.8 mL:1.2mL, viscosity is 7.36 mPas) (DMF: glycerin=5:5=1.5 mL:1.5mL, viscosity is 14.2 mPas), (DMF: glycerin=4:6=1.2 mL:1.8mL, viscosity is 19.9 mPas), (DMF: glycerin=3:7=0.9 mL:2.1mL, viscosity is 64.6 mPas), (DMF=2:8=0.6:2.127:4:4=1.5 mL, and (DMF: 5:5=1.5:1.5 mL:1.8mL, 37 mL) of fluorescent light is obtained by linear measurement, and the linear relation between the fluorescent light emission and the fluorescent light emission is shown in fig. 25 g, wherein the fluorescent light emission is obtained in the linear relation of the fluorescent light emission of each of the fluorescent light emission device. Y-1 itself is weak in fluorescence, but as the viscosity increases, the fluorescence intensity gradually increases. The viscosity coefficient was 3.83 and the maximum fluorescence enhancement to viscosity was 2.4 times.
Example 8 response of Compound Y-3 to viscosity
Weighing compound Y-3 (5.33 mg,0.01 mmol), dissolving 1mL of DMF to prepare 0.01mol/L mother liquor, and then dissolving 10. Mu.L of each mother liquor into 3mL of mixture of DMF and glycerol with different viscosities to prepare 33.3. Mu.mol/L of solution to be tested (DMF: glycerol=7:3=2.1 ml:0.9mL, viscosity 4.22 mpa.s), (DMF: glycerol=6:4=1.8 ml:1.2mL, viscosity 7.36 mpa.s) (DMF: glycerol=5:5=1.5 ml:1.5mL, viscosity 14.2 mpa.s), (DMF: glycerol=4:6=1.2 ml:1.8mL, viscosity 19.9 mpa.s), (DMF: glycerol=3:7=0.9 ml:2.1mL, viscosity 64.6 mpa.s), (DMF: glycerol=2:8=0.6 ml:2.4mL, viscosity 127.5 mpa.s), (DMF: glycerol=1:9=0.3 ml:2.7mL, viscosity 258.7 mpa.s) to obtain the fluorescence spectra of these, respectively, to obtain fig. 9, and fitting the linear relationship of fluorescence intensity logI 807nm to log η to obtain the maximum fluorescence enhancement of fig. 10, viscosity coefficient of 4.70, viscosity to 1.4.4 times.
Example 9 response of Compound Y-4 to viscosity
Weighing compound Y-4 (5.05 mg,0.01 mmol), dissolving 1mL of DMF to prepare 0.01mol/L mother liquor, and then dissolving 10. Mu.L of each mother liquor into 3mL of mixture of DMF and glycerol with different viscosities to prepare 33.3. Mu.mol/L of solution to be tested (DMF: glycerol=7:3=2.1 ml:0.9mL, viscosity 4.22 mpa.s), (DMF: glycerol=6:4=1.8 ml:1.2mL, viscosity 7.36 mpa.s) (DMF: glycerol=5:5=1.5 ml:1.5mL, viscosity 14.2 mpa.s), (DMF: glycerol=4:6=1.2 ml:1.8mL, viscosity 19.9 mpa.s), (DMF: glycerol=3:7=0.9 ml:2.1mL, viscosity 64.6 mpa.s), (DMF: glycerol=2:8=0.6 ml:2.4mL, viscosity 127.5 mpa.s), (DMF: glycerol=1:9=0.3 ml:2.7mL, viscosity 258.7 mpa.s) to obtain the fluorescence spectra of fig. 11, and fitting the linear relationship of fluorescence intensity log i 807nm to η to obtain the maximum fluorescence enhancement of fig. 12, viscosity coefficient of 4.20 to 2.3.20 times.
The above embodiments are merely preferred embodiments of the present application, and should not be construed as limiting the present application, and the embodiments and features of the embodiments of the present application may be arbitrarily combined with each other without collision. The protection scope of the present application is defined by the claims, and the protection scope includes equivalent alternatives to the technical features of the claims. I.e., equivalent replacement modifications within the scope of this application are also within the scope of the application.
Claims (8)
1. A seven-membered bopyin-based heterocyclic compound, which is characterized by having the chemical structural formula:
；
Wherein, the substituent R is any one selected from hydrogen, methoxy, bromine and cyano.
2. The method of synthesizing a heterocyclic compound of claim 1, comprising the following synthetic pathways:
；
Wherein the substituent R is any one selected from hydrogen, methoxy, bromine and cyano
(1) Adding a compound 1, a compound 2 and toluene into a reaction bottle at room temperature, performing ultrasonic dissolution, adding piperidine, and heating to obtain a reaction solution;
(2) And (3) performing rotary evaporation on the reaction liquid in the step (1), and separating by silica gel column chromatography to obtain a product Y.
3. The method of claim 2, wherein in the step (1), the feeding molar ratio of the compound 1, the compound 2 and the piperidine is 1:1-2: 0.3 to 1.
4. The method of claim 2, wherein the heating temperature in step (1) is 20-100 ℃ and the heating time is 2-5 hours.
5. The method of claim 2, wherein compound 1 in step (1) is a para derivative of seven membered heterocyclic ring bopyin.
6. Use of the seven-membered bopyin heterocyclic compound as described in claim 1 for detecting viscosity in an organic solution.
7. The use according to claim 6, wherein the organic solution comprises DMF, glycerol.
8. The use according to claim 6, wherein the viscosity detection range is 0.3-300 mpa.s.
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