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Preparation and application of aggregation-induced light emitting compound based on naphthalimide

A technology of aggregation-induced luminescence and naphthalimide, which is applied in the field of fluorescence imaging to achieve the effect of shortening the reaction time, reducing the generation of by-products, and having good solubility

Active Publication Date: 2020-06-09
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Dyes with AIE properties In addition to polytetraphenylethylene and its analogs developed by Tang Benzhong's team, some polyalkane chain-modified naphthalimide dyes have also been gradually reported to have AIE, but the common point of AIE naphthalimides currently reported is the use of long The 9-N is modified by the alkane chain or substituted alkane chain, and the commonly used modification site of naphthalimide is the 4-position, while the 4-position modified AIE naphthalimide is rarely reported

Method used

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  • Preparation and application of aggregation-induced light emitting compound based on naphthalimide
  • Preparation and application of aggregation-induced light emitting compound based on naphthalimide
  • Preparation and application of aggregation-induced light emitting compound based on naphthalimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of DiNMeQ: N 2 Under atmosphere, 4-bromo-1,8-naphthalic anhydride (2.77g, 10mmol) and 40% aqueous methylamine solution (5.2ml, 50mmol) were added to DMSO, stirred at 80°C for 3 hours and then cooled to room temperature. The reaction solution was then poured into ice water, and the precipitated precipitate was filtered and dried. Finally, the crude product was purified by column chromatography (eluent, petroleum ether: ethyl acetate = 5:1) to obtain DiNMeQ as a yellow solid with a yield of 72%.

[0037] 1 H NMR (600MHz, (CD 3 ) 2 SO) δ8.61(d, J=9.0Hz, 1H), δ8.43(d, J=7.2Hz, 1H), δ8.29(d, J=8.4Hz, 1H), δ7.92(m, 1H), δ7.68 (t, J = 7.8Hz, 1H), δ3.35 (s, 3H), δ2.99 (d, J = 4.8Hz, 3H).

[0038] 13 C NMR (600MHz, (CD 3 ) 2 SO) δ164.54, 163.46, 151.87, 134.86, 131.13, 129.33, 128.81, 124.52, 122.20, 120.77, 108.07, 103.78, 29.99, 26.59;

[0039] HRMS(MALDI-TOF):m / z calcd.for[C 14 h 13 N 2 o 2 + ][M+H] + :241.0977, found241.0980.

Embodiment 2

[0041] Preparation of 6BrNMeQ: N 2 Under the atmosphere, NaH (60% dispersed in kerosene, 3mmol) was slowly added to the dry DiNMeQ (0.24g, 1mmol) THF suspension under the condition of ice bath, stirred continuously and refluxed for 2h, then added 1,6 - Dibromohexane (438uL, 3mmol) and continue to reflux overnight. After most of the raw materials are converted, the solvent in the reaction solution is evaporated by rotary evaporation, and the solid crude product is directly separated and purified by column chromatography (eluent: petroleum ether: ethyl acetate = 10:1), and the obtained 6BrNMeQ is a bright yellow solid with a yield of 39%.

[0042] 1 H NMR (600MHz, CDCl 3 ), δ8.50(d, J=8.0Hz, 1H), δ8.60(d, 8.0Hz, J=8.0Hz, 1H), δ8.47(d, J=8.0Hz, 1H), δ7.69 (t,J=8.0Hz,1H),δ7.19(d,J=8.0Hz,1H),δ3.55(s,3H),δ3.36(m,4H),δ3.06(s,3H ), δ1.84(m, 2H), δ1.75(m, 2H), δ1.40(m, 2H), δ1.35(m, 2H);

[0043] 13 C NMR (600MHz, (CD 3 ) 2 SO), δ164.38, 163.74, 156.83, 132.57, 131.51, 130.96,...

Embodiment 3

[0046] Preparation of 6ANMeQ: N 2 Under atmosphere, compound 6BrNMeQ (0.403g, 1mmol), 4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-alcohol (0.32g, 1mmol), and Cs 2 CO 3 (0.650g, 2mmol) was dissolved in dry DMF. After reacting at room temperature for 3h, the solvent was removed by rotary evaporation, and column chromatography (eluent: dichloromethane:methanol=40:1) gave compound 6ANMeQ with a yield of 64%. .

[0047] 1 H NMR (400M, CDCl 3 )δ8.64(s,1H),δ8.55(d,J=7.2Hz,1H),δ8.45 (d,J=8.0Hz,1H),δ8.37(d,J=8.4Hz,1H ),δ7.87(m,1H),δ7.74(s,1H),δ7.62 (t,J=8.0Hz,1H),δ7.56(m,1H),δ7.23(s,1H ),δ7.12(t,J=8.8Hz,3H),δ3.95(m,5H),δ3.53(s,3H),δ3.35(t,J=7.2Hz,2H),δ3. 04(s,3H),δ1.75(m,4H), δ1.34(m,4H);

[0048] 13 C NMR (400M, CDCl 3 )δ164.98,164.42,156.97,156.22,155.22, 153.26,149.18,147.29,132.54,131.16,131.02,130.02,125.72,124.98, 124.17,122.91,121.78,121.71,121.08,120.90,116.54,116.39,114.82, 114.44,108.87 ,107.70,69.32,56.78,56.06,41.42,28.96,27.22,26.94,26.61,25.61.

[0049]...

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Abstract

The invention relates to a preparation method of two 4-substituted naphthalimide derivatives, and application of the 4-substituted naphthalimide derivatives in fluorescence imaging, wherein the structures of the two compounds are respectively represented by 6BrNMeQ and 6ANMeQ. At present, most of reported naphthalimide compounds with aggregation-induced emission properties are derivatives with 9-position N- substituted by long-chain alkane; 6BrNMeQ and 6ANMeQ are two new compounds of which the 6-position of naphthalimide is modified by a hexane chain, wherein the 6ANMeQ is obtained by carryingout a nucleophilic substitution reaction on the 6BrNMeQ and 4-(3-chloro-4-fluorophenylamino)-7-methoxyquinazoline-6-alcohol, and the two compounds have obvious aggregation-induced emission properties, can emit green fluorescence in an aqueous solution or a solid state, and are sensitive to environmental polarity. According to the spectral properties, 6ANMeQ with high aggregation state quantum yield is applied to cancer cell lipid droplet imaging.

Description

technical field [0001] The present invention relates to the field of fluorescence imaging in the field of organic synthesis and biotechnology, specifically, the preparation method of two 4-substituted methylamino-1,8 naphthalimide compounds and the imaging analysis of cancer cells. Background technique [0002] The fluorescence method can reflect the signal of the system in a highly sensitive and non-invasive manner in real time, and has significant advantages in sample analysis. The development of fluorescent probes and biomarker imaging technologies has broadened the application of fluorescence methods in the fields of biology, environment, and medicine. Fluorescent probes include on-off and off-on types. In the actual detection process, there are many environmental factors that can cause fluorescence quenching. In comparison, fluorescent off-on probes or dyes can more accurately react Quantity or process change of the measurement system. Most of the commonly used commerc...

Claims

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Application Information

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IPC IPC(8): C07D221/20C07D401/12C09K11/06G01N21/64
CPCC07D221/20C07D401/12C09K11/06G01N21/6428C09K2211/1029C09K2211/1044C09K2211/1007G01N2021/6432
Inventor 韩克利王艳妮李鹏
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI