CN110759871B - Camphor synthesized quinazoline compound used as fluorescent probe for hypochlorous acid detection - Google Patents
Camphor synthesized quinazoline compound used as fluorescent probe for hypochlorous acid detection Download PDFInfo
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Abstract
The invention discloses a quinazoline compound synthesized by camphor and used as a fluorescent probe for hypochlorous acid detection. The method utilizes natural renewable resources camphor as raw materials, and the raw materials are condensed with salicylaldehyde to generate 3- (2' -hydroxybenzene methylene) camphor; and carrying out condensation cyclization on the 3- (2 '-hydroxybenzylidene) camphor and guanidine hydrochloride to obtain the 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline. The compound can be specifically oxidized by hypochlorous acid and generates green fluorescence under the irradiation of 365nm ultraviolet light, so that the compound can be used as a fluorescent probe for detecting the hypochlorous acid and has good application prospect.
Description
Technical Field
The invention belongs to the technical field of fine organic synthesis, and relates to a method for synthesizing quinazoline compounds by using camphor as a raw material and using the quinazoline compounds as fluorescent probes for hypochlorous acid detection.
The invention discloses a quinazoline compound synthesized by camphor and used as a fluorescent probe for hypochlorous acid detection. The method utilizes natural renewable resources camphor as raw materials, and the raw materials are condensed with salicylaldehyde to generate 3- (2' -hydroxybenzene methylene) camphor; and carrying out condensation cyclization on the 3- (2 '-hydroxybenzylidene) camphor and guanidine hydrochloride to obtain the 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline. The compound can be specifically oxidized by hypochlorous acid and generates green fluorescence under the irradiation of 365nm ultraviolet light, so that the compound can be used as a fluorescent probe for detecting the hypochlorous acid and has good application prospect.
Background
Hypochlorous acid (HClO) is a commonly used disinfectant and bleaching agent in our lives and plays a very critical role in the human immune system. However, in humans, hypochlorous acid levels above normal levels can induce a number of inflammation-related disorders, such as arteriosclerosis, rheumatoid arthritis, pneumonia, cardiovascular and renal diseases. Therefore, the development of an analysis method for detecting hypochlorous acid has a positive significance for clinical diagnosis and treatment of the diseases.
Compared with the traditional analysis method, the small-molecule fluorescent probe attracts more and more researchers with the advantages of high selectivity, high sensitivity, simplicity and the like. The natural renewable resource camphor is used as a raw material to synthesize a novel fluorescent probe for detecting hypochlorous acid.
Disclosure of Invention
The purpose of the invention is as follows: aiming at the defects in the prior art, the invention aims to provide a quinazoline compound fluorescent probe which is synthesized by taking camphor as a raw material and is used for detecting hypochlorous acid.
The technical scheme is as follows: in order to achieve the purpose, the invention adopts the technical scheme that:
the quinazoline compound is 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline, and the structural formula is as follows:
the synthetic method of the quinazoline compound comprises the following steps:
1) and performing aldol condensation on the camphor and salicylaldehyde to obtain the 3- (2' -hydroxybenzylidene) camphor.
2)3- (2 '-hydroxybenzylidene) camphor and guanidine hydrochloride are subjected to condensation reaction to obtain 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline.
In the step 1), camphor and salicylaldehyde are subjected to aldol condensation to obtain 3- (2' -hydroxybenzylidene) camphor, and the specific preparation method comprises the following steps:
(1) 0.1mol of camphor, 0.1-0.15 mol of salicylaldehyde, 0.2-0.3 mol of potassium tert-butoxide and 0.1-0.3L of tert-butanol are sequentially added into a three-neck flask provided with a stirrer, a thermometer and a reflux condenser, and the reaction is carried out at the temperature of 0-100 ℃ under the protection of nitrogen.
(2) Extracting the reaction solution with 0.3-0.5L ethyl acetate for 3 times, combining organic phases, washing with saturated saline solution to be neutral, drying the organic phase with anhydrous sodium sulfate, filtering, concentrating and recovering the solvent to obtain a crude product of the 3- (2' -hydroxybenzylidene) camphor.
(3) Recrystallizing the crude product of the 3- (2 '-hydroxybenzylidene) camphor with methanol-ethyl acetate to obtain a pure product of the 3- (2' -hydroxybenzylidene) camphor.
In the step 2), 3- (2 '-hydroxybenzylidene) camphor reacts with guanidine hydrochloride under the action of potassium tert-butoxide to obtain 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline, and the specific preparation method comprises the following steps:
(1) sequentially adding 0.1mol of 3- (2 '-hydroxybenzylidene) camphor, 0.4-0.6 mol of guanidine hydrochloride, 0.4-1.0 mol of potassium tert-butoxide and 0.2-0.4L of tert-butanol into a three-neck flask provided with a stirrer, a thermometer and a reflux condenser, heating and refluxing for 18 hours under the protection of nitrogen, and terminating the reaction until the conversion rate of the 3- (2' -hydroxybenzylidene) camphor reaches 95% by GC tracking detection.
(2) Extracting the reaction solution for 3 times by using 0.4-0.8L ethyl acetate, combining organic phases, washing the organic phases to be neutral by using saturated saline solution, drying the organic phases by using anhydrous sodium sulfate, filtering, concentrating and recovering a solvent to obtain a crude product of the 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline.
(3) Recrystallizing the crude product of the 2-amino-4- (2 '-hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline with ethanol-ethyl acetate to obtain white blocky crystals of the 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline.
The 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline is used as a fluorescent probe for detecting hypochlorous acid.
The invention uses natural renewable resources camphor as raw materials, and the natural renewable resources camphor and salicylaldehyde are condensed to generate 3- (2' -hydroxybenzene methylene) camphor; condensing and cyclizing 3- (2 '-hydroxybenzylidene) camphor and guanidine hydrochloride to obtain 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline; the compound can specifically recognize hypochlorous acid and can be used as a fluorescent probe for detecting hypochlorous acid.
Has the advantages that: compared with the prior art, the quinazoline compound prepared by using natural renewable resource camphor as a raw material can specifically identify hypochlorous acid, can be specifically oxidized by the hypochlorous acid to generate green fluorescence, and therefore, the compound can be used as a fluorescent probe for detecting the hypochlorous acid and has good practical value.
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FIG. 1 is a graph showing the effect of hypochlorous acid concentration on the fluorescence spectrum of 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline;
FIG. 2 is a graph showing the effect of different ions on the fluorescence spectrum of 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline;
Detailed Description
The present invention will be further described with reference to the following specific examples.
Example 1
The synthetic method of the quinazoline compound comprises the following steps:
the method comprises the following specific steps:
1) preparation of 3- (2' -hydroxybenzylidene) camphor:
heating 2mmol of camphor, 3mmol of salicylaldehyde, 4mmol of sodium ethoxide and 20mL of ethanol in a three-neck flask with a stirrer, a thermometer and a reflux condenser in sequence at 80-90 ℃ until the reflux is carried out for reaction for about 6 hours until the camphor conversion rate reaches more than 95% (GC tracking detection). Extracting the reaction solution with 25mL ethyl acetate for 3 times, combining organic phases, washing with saturated saline solution to be neutral, drying the organic phase with anhydrous sodium sulfate, filtering, concentrating and recovering the solvent to obtain the 3- (2' -hydroxybenzylidene) camphorRecrystallizing the crude brain product by using ethanol-ethyl acetate to obtain yellow and transparent 3- (2' -hydroxybenzylidene) camphor, wherein the yield is 87.0%, the purity is 98.7%, and the melting point is 224.1-224.3 ℃;1H NMR(400MHz，CDCl3)δ：7.39(d，J＝8Hz，2H)，7.19(s，1H)，6.88(d，J＝8Hz，2H)，3.09(d，J＝4Hz，1H)，2.13-2.21(m，1H)，1.75-1.81(m，1H)，1.48-1.60(m，2H)，1.03(s，3H)，1.00(s，3H)，0.81(s，3H)；13C NMR(100MHz，CDCl3)δ：208.99，156.59，139.84，131.66，128.15，127.77，115.74，57.15，49.20，46.90，30.87，25.88，20.56，18.40，9.32；EIMS m/z(％)：256(M+，46)，213(51)，172(100)，157(40)，144(31)，115(64)，107(39)，91(39)，77(39)，55(38)。
2) preparation of 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline:
adding 1mmol of 3- (2 '-hydroxybenzylidene) camphor, 4mmol of guanidine hydrochloride, 6mmol of potassium tert-butoxide and 30mL of tert-butanol into a three-neck flask with a stirrer, a thermometer and a reflux condenser in sequence, heating to reflux at 80-90 ℃ for reaction for about 18 hours until the conversion rate of the 3- (2' -hydroxybenzylidene) camphor reaches more than 95% (GC tracking detection). Extracting the reaction liquid for 3 times by using ethyl acetate, combining organic phases, washing the organic phases to be neutral by using saturated saline solution, drying the organic phases by using anhydrous sodium sulfate, filtering, concentrating and recovering a solvent to obtain a crude product of 2-amino-4- (2 '-hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline, and recrystallizing the crude product by using methanol-ethyl acetate to obtain a white blocky crystal of the 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline, wherein the yield is 89.0%, the purity is 98.6%, and the melting point is 167.9-168.3 ℃;1H NMR(400MHz，CDCl3)δ：7.65(d，J＝8Hz，1H)，7.31(t，J＝8Hz，1H)，7.0(d，J＝8Hz，1H)，6.9(d，J＝16Hz，1H)，5.21(s，2H)，3.27(d，J＝4Hz，1H)，2.21-2.29(m，1H)，1.90-1.96(m，1H)，1.31-1.43(m，2H)，1.24(s，3H)，1.00(s，3H)，0.63(s，3H)；13C NMR(100MHz，CDCl3)δ：183.33，159.85，159.01，155.66，131.66，129.11，123.93，119.21，118.64，118.22，55.72，54.22，50.86，31.88，25.35，19.94，18.99，10.03；HRMS(m/z)：[M+H]+calcd for C18H21N3O，296.1763；found，296.1758。
example 2
Preparing a certain amount of 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline into 1 x 10-5M PBS buffer solution, hypochlorous acid is dissolved in PBS buffer solution to prepare solution with concentration of 0, 5, 10, 15, 20, 25, 30, 35, 40, 45 and 50 μ M. The fluorescence emission spectra of hypochlorous acid at various concentrations on 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline were measured, as shown in FIG. 1. The results show that the blue fluorescence of the solution is gradually weakened and the green fluorescence is gradually strengthened along with the continuous increase of the concentration of the hypochlorous acid in the system, thereby indicating that the compound can be used as a fluorescent probe for sensitively detecting the hypochlorous acid.
Example 3
Preparing a certain amount of 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline into 1 x 10-5M in PBS buffer, various ions were similarly dissolved in PBS buffer to make the concentration 1X 10-4A solution of M. Fluorescence emission spectra of different ion pairs of 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline were measured, as shown in fig. 2. The results show that the addition of hypochlorous acid causes a significant change in the fluorescence intensity of the system, while other ions, such as H, are added2O2，ONOO-，O2 -，t-BuOOH，NO2 -，Na+，K+，Zn2+，Cu2+，Al3+，Ni+，Ca2+，F-，Cl-，CO3 2-，SO4 2-，HS-，ClO4 -The fluorescence spectrum of the solution is not changed significantly by iso-reference observationThus, the compound can be used as a fluorescent probe for specifically recognizing hypochlorous acid.
Claims (3)
1. A synthetic method of quinazoline compounds, which is characterized in that 1) camphor and salicylaldehyde are subjected to aldol condensation to obtain 3- (2' -hydroxybenzylidene) camphor; 2) carrying out condensation reaction on 3- (2 '-hydroxybenzylidene) camphor and guanidine hydrochloride to obtain 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline;
the specific preparation method of the step 1) comprises the following steps:
(1) sequentially adding 0.1mol of camphor, 0.1-0.15 mol of salicylaldehyde, 0.2-0.3 mol of potassium tert-butoxide and 0.1-0.3L of tert-butyl alcohol into a three-neck flask provided with a stirrer, a thermometer and a reflux condenser, and reacting at 0-100 ℃ under the protection of nitrogen;
(2) extracting the reactant with 0.3-0.5L ethyl acetate for 3 times, combining organic phases, then washing with saturated saline solution to neutrality, drying the organic phase with anhydrous sodium sulfate, filtering, concentrating and recovering the solvent to obtain a crude product of the 3- (2' -hydroxybenzylidene) camphor;
(3) recrystallizing the crude product of the 3- (2 '-hydroxybenzylidene) camphor with methanol-ethyl acetate to obtain 3- (2' -hydroxybenzylidene) camphor;
the 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline structure is
2. The method for synthesizing quinazoline compounds according to claim 1, wherein in the step 2), 3- (2 '-hydroxybenzylidene) camphor reacts with guanidine hydrochloride under the action of potassium tert-butoxide to obtain 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline, and the specific preparation method comprises the following steps:
(1) sequentially adding 0.1mol of 3- (2' -hydroxybenzylidene) camphor, 0.4-0.6 mol of guanidine hydrochloride, 0.4-1.0 mol of potassium tert-butoxide and 0.2-0.4L of tert-butanol into a three-neck flask provided with a stirrer, a thermometer and a reflux condenser, heating and carrying out reflux reaction for 18h under the protection of nitrogen, and tracking and detecting the reaction by using GC;
(2) extracting the reaction solution for 3 times by using 0.4-0.8L ethyl acetate, combining organic phases, washing the organic phases to be neutral by using saturated saline solution, drying the organic phases by using anhydrous sodium sulfate, filtering, concentrating and recovering a solvent to obtain a crude product of 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methanoquinazoline;
(3) recrystallizing the crude product of the 2-amino-4- (2 '-hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline by methanol-ethyl acetate to obtain white blocky crystals of the 2-amino-4- (2' -hydroxyphenyl) -8, 9, 9-trimethyl-5, 6, 7, 8-tetrahydro-5, 8-methano quinazoline.
3. The application of a quinazoline compound as a fluorescent probe for hypochlorous acid detection is provided, and the quinazoline compound has a structure
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| CN111607007B (en) * | 2020-06-19 | 2022-03-25 | 南京林业大学 | Cellulose-based Schiff base fluorescent material and preparation method and application thereof |
| CN111808109B (en) * | 2020-06-29 | 2022-03-25 | 南京林业大学 | Pyridazine quinoxaline diamine Schiff base cobalt ion fluorescent probe and preparation method thereof |
| CN111747898B (en) * | 2020-07-08 | 2021-11-02 | 南京林业大学 | 2, 3-pindione imidazole type fluorescent probe for detecting hypochlorous acid and preparation method and application thereof |
| CN113603593B (en) * | 2021-09-22 | 2022-06-10 | 南京林业大学 | Camphor-based fluorescent probe for detecting cysteine, and preparation method and application thereof |
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