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Near-infrared fluorescent dye containing 4-dicyanomethylbenzopyran unit and its preparation method and application

A cyanomethylbenzopyran and near-infrared dye technology, which can be used in methine/polymethine dyes, styryl dyes, luminescent materials, etc., can solve problems such as interference with fluorescent imaging effects, and achieve broad application prospects , The synthesis route is simple, and the effect of increasing the emission wavelength

Active Publication Date: 2022-06-14
武汉振豪生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Biological tissues have strong autofluorescence and severe light absorption in the range of <700nm, which will seriously interfere with the fluorescence imaging effect

Method used

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  • Near-infrared fluorescent dye containing 4-dicyanomethylbenzopyran unit and its preparation method and application
  • Near-infrared fluorescent dye containing 4-dicyanomethylbenzopyran unit and its preparation method and application
  • Near-infrared fluorescent dye containing 4-dicyanomethylbenzopyran unit and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of Compound 2

[0028] Under ice bath conditions, POCl 3 (7.83 mL, 10 eq) was dropped into DMF (7.77 mL, 11 eq), and the reaction was maintained at this temperature for 2 hours. Under ice bath conditions, compound 1 (3.5 g, 7.18 mmol) was dissolved in 2 mL of DMF, dropped into the reaction system, and reacted at room temperature overnight. After the reaction was completed, the reaction was directly poured into ice water, and the pH of the solution was adjusted to near neutrality with sodium carbonate, then extracted with EA, washed three times with water (50 mL×3), and washed three times with saturated saline (50 mL×3). The organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was spin-dried through a silica gel column (PE:EA=20:1) to obtain 3.5 g of compound 2. Yield: 94%.

[0029] The compound structure determination data are as follows:

[0030] 1 H NMR (400MHz, CDCl 3 )δ9.80(s, 1H), 7.68(d, J=8.6Hz, 2H), 7.34(t...

Embodiment 2

[0033] Example 2: Preparation of Compound 4

[0034] Take compound 2 (445 mg, 1 mmol) and compound 3 (208 mg, 1 mmol) into a 100 mL round-bottomed flask, add 45 mL of toluene to dissolve under argon protection, add 0.5 mL of piperidine, 0.5 mL of acetic acid, and under argon protection at 115 ° C The reaction was heated under reflux in an oil bath for 12 hours. After the reaction was completed, it was cooled to room temperature, toluene was removed by rotary evaporation, and 417 mg of compound 4 was obtained by separation and purification on a silica gel column (PE:EA=10:1). Yield: 65%.

[0035] The structural determination data of compound 4 are as follows:

[0036] 1 H NMR (400MHz, CDCl 3 )δ8.91(d,J=8.3Hz,1H),7.78-7.70(m,1H),7.62-7.54(m,2H),7.44(t,J=8.9Hz,3H),7.34(t,J =7.8Hz,2H),7.21–7.14(m,5H),7.07(dd,J=26.8,8.5Hz,4H),6.81(s,1H),6.64(d,J=15.8Hz,1H),4.30 –4.16(m,2H),2.97(t,J=7.8Hz,2H),2.65(t,J=7.8Hz,2H),1.08–0.96(m,2H),0.07(s,9H)

[0037] 13 C NMR (101MHz, CDCl 3)δ1...

Embodiment 3

[0039] Example 3: Preparation of Compound 5

[0040] Compound 4 (20 mg, 0.03145 mmol) was taken into a 5 mL round-bottomed flask, 1 mL of dichloromethane was added under argon protection, placed in an ice bath, and 0.5 mL of trifluoroacetic acid was added dropwise. The reaction solution was mechanically stirred for 6 hours at 25°C. After the reaction was completed, the solvent was directly evaporated by rotary evaporation, and separated and purified by silica gel column (DCM:MeOH=20:1) to obtain 15 mg of compound 5 with a yield of 89%.

[0041] The structural determination data of compound 5 are as follows:

[0042] 1 H NMR (400MHz, CDCl 3 )δ8.92(dd,J=8.4,1.0Hz,1H),7.78-7.71(m,1H),7.61-7.54(m,2H),7.49-7.41(m,3H),7.34(t,J= 7.8Hz, 2H), 7.17(dd, J=15.1, 6.4Hz, 5H), 7.07(dd, J=26.3, 8.5Hz, 4H), 6.83(s, 1H), 6.66(d, J=15.8Hz, 1H), 2.99(t, J=7.7Hz, 2H), 2.74(t, J=7.7Hz, 2H).

[0043] 13 C NMR (101MHz, CDCl 3 )δ177.84,158.22,152.87,152.38,150.24,146.60,144.91,138.77,136.45,13...

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Abstract

The invention discloses a near-infrared fluorescent imaging agent containing 4-dicyanomethylbenzopyran and triphenylamine and a preparation method thereof. A modifiable group is introduced on the triphenylamine of the fluorescent compound, and the increased modifiable sites can be used to connect different biologically active substances, thereby improving its water solubility and biocompatibility, and expanding its application range in the biomedical field. The fluorescent imaging agent of the invention has the advantages of high fluorescence intensity, non-toxicity, good biocompatibility, etc., and has excellent application prospects. The invention also discloses the application of the fluorescent imaging agent in the field of tumor imaging. In addition, the imaging agent has good modifiability and can also be used for in vitro detection of various disease markers.

Description

technical field [0001] The invention belongs to the field of tumor fluorescence imaging in the field of biomedical materials, and in particular relates to a class of modifiable near-infrared dyes containing 4-dicyanomethylbenzopyran units and a preparation method thereof, and in the field of biomedical fluorescence imaging Applications. Background technique [0002] Cancer (also known as malignant tumor) is a serious threat to human health. Due to the limitation of medical technology, there is currently no effective treatment for advanced cancer, so early diagnosis of cancer is particularly important for patients. If the tumor can be diagnosed early and treated in time, the survival rate of cancer patients can be significantly improved. The emergence of molecular imaging techniques such as non-invasive intravital fluorescence imaging has opened up a new development path for the early diagnosis of cancer. [0003] Biological tissues have strong autofluorescence and serious ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/04C07D335/06C07D345/00C07D409/12C09K11/06C09B23/14A61K49/00G01N21/64
CPCA61K49/0021A61P35/00G01N21/6428C09K11/06C07D311/04C07D335/06C07D345/00C07D409/12C09B23/145C09K2211/1088C09K2211/1092C09K2211/1096C09K2211/1029C09K2211/1007C09K2211/1014
Inventor 田间洪学传陈梓杨
Owner 武汉振豪生物科技有限公司
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