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Preparation method and application of heptamethine benzo indole cyanine dye

A technology of benzoindole cyanine and benzindole derivatives, which is applied in the field of polymethylindole cyanine dyes and its preparation, can solve the problems of large consumption of organic solvents, low purity and high price, and avoid precious metals Catalysis, a large amount of single reaction, and the effect of improving the production efficiency

Pending Publication Date: 2020-09-15
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the heptamethine indole cyanine sold in the market is only a new indocyanine green (IR-820), and the purity is low (80%), and the price is high (1324 yuan / g)
At the same time, the production and purification process of its different derivatives requires a lot of condition screening and consumes a lot of organic solvents, and most of the selected solvents are highly toxic solvents, such as o-dichlorobenzene, toluene, benzene, etc.

Method used

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  • Preparation method and application of heptamethine benzo indole cyanine dye
  • Preparation method and application of heptamethine benzo indole cyanine dye

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preparation example Construction

[0138] As mentioned above, the present application relates to a preparation method of heptamethylbenzindole cyanine dye, comprising the following steps: combining 2,3,3-trimethyl-4,5-benzindole derivatives with Reacting the nuclear substitution compound to obtain an organic ammonium salt; mixing the organic ammonium salt and cycloalkene derivatives in an environment-friendly organic solvent for reaction, adding an organic precipitating agent to the product after cooling and standing overnight to obtain the heptamethylbenzindol Indocyanine dyes. The method has the advantages of short synthesis route, simple process, no catalyst, high yield, simple purification method, high atom utilization rate and less consumption of organic solvents, can greatly improve the preparation efficiency of such dyes, and realize low-cost mass production , which is of great significance in the production and application research of heptamethine benzindole cyanine dyes.

[0139] In addition, the prep...

Embodiment 1

[0146] Embodiment 1 synthetic compound 53

[0147] Compound 53 was synthesized according to the following route:

[0148]

[0149] 1) Synthesis of 2,3,3-trimethyl-1-(butane)-4,5-benzindole

[0150] Add 2,3,3-trimethyl-4,5-benzindole and 4-bromobutane at a molar ratio of 1:1.5 into the reactor, close the reactor and then evacuate to 10Pa. The reaction system was heated to 110° C. and stirred for 8 hours, then cooled to room temperature. The obtained product was filtered with suction and used directly for the next reaction.

[0151] 2) Synthesis and purification of compound 53

[0152] 2-chloro-1- Formyl-3-hydroxymethylenecyclopentene. After completely dissolving with methanol, the reaction system was heated to 75° C. for 24 hours under closed conditions, then cooled to room temperature, and placed in a 4° C. refrigerator for 24 hours. Petroleum ether was added, then allowed to stand and filtered with suction. The resulting solid was dried in vacuo to give the product ...

Embodiment 2

[0154] Embodiment 2 synthetic compound 26

[0155] Compound 26 was synthesized according to the following route:

[0156]

[0157] 1) Synthesis of 2,3,3-trimethyl-1-(p-toluic acid)-4,5-benzindole

[0158] Add 2,3,3-trimethyl-4,5-benzindole and p-bromomethylbenzoic acid at a molar ratio of 1:1.5 into the reactor, and seal the reactor and then evacuate it to 15Pa. The reaction system was heated to 110° C. and stirred for 12 hours, then cooled to room temperature. The obtained product was filtered with suction and used directly for the next reaction.

[0159] 2) Synthesis and purification of compound 26

[0160] Add 2-chloro- 1-Formyl-3-hydroxymethylenecyclohexene. After completely dissolving with methanol, the reaction system was heated to 75° C. for 24 hours under closed conditions, then cooled to room temperature, and placed in a 4° C. refrigerator for 24 hours. Petroleum ether was added, then allowed to stand and filtered with suction. The resulting solid was dried ...

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Abstract

The invention discloses a preparation method and application of a heptamethine benzo indole cyanine dye, and belongs to the field of polymethine indole cyanine dyes and preparation thereof. The methodcomprises the following steps: 1) carrying out a heating reaction on raw materials containing a 2,3,3-trimethyl-4,5-benzoindole derivative and a nucleophilic substituted compound under a vacuum condition to obtain an organic ammonium salt; and 2) carrying out a heating reaction on a solution containing the organic ammonium salt obtained in the step 1) and a cycloalkene derivative under a closed condition, wherein the structural formula of the heptamethine benzo indole cyanine dye is represented by a formula (I). According to the invention, the dye has near-infrared light absorption and fluorescence development performances and can be used as a probe auxiliary agent; and the method has the advantages of short synthesis route, environment-friendly solvent, simple process, avoidance of noblemetal catalysis, high yield, high product purity and the like, is high in applicability, and can be used for synthesizing products of various structure types.

Description

technical field [0001] The application relates to a preparation method and application of heptamethinebenzindole cyanine dye, and belongs to the field of polymethylbenzindole cyanine dye and its preparation. Background technique [0002] The indocyanine green in the heptamethine cyanine dye is the only near-infrared dye approved by the US Food and Drug Administration for clinical photothermal therapy, and its derivative new indocyanine green belongs to the heptamethine indocyanine dye kind of. This type of dye has a strong absorption effect in the near-infrared region around 808nm, which can be used as a complement to other medical diagnosis and treatment methods (such as MRI, PET, SPECT, ultrasound echo scanning technology, radiography and tomography) Imaging technology, also used as a photosensitizer for photothermal therapy, has important research and application value in life science and biomedical research. [0003] Heptamethine indole cyanine dyes have multiple modif...

Claims

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Application Information

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IPC IPC(8): C09B23/08C07D209/60C09K11/06G01N21/64A61K49/00
CPCA61K49/0032C07D209/60C09B23/0066C09B23/08C09K11/06C09K2211/1007C09K2211/1029G01N21/643A61K49/00G01N21/64
Inventor 吴爱国蒋振奇袁博李娟
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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