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Heptamethine nitroindole cyanine dye, preparation method and application thereof

A technology of nitroindole cyanine and heptamethine, applied in the field of polymethine indole cyanine dye and its preparation, can solve the problems of high price, low purity, and large consumption of organic solvents

Active 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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  • Heptamethine nitroindole cyanine dye, preparation method and application thereof
  • Heptamethine nitroindole cyanine dye, preparation method and application thereof
  • Heptamethine nitroindole cyanine dye, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0155] Example 1 Synthesis of 2,3,3-trimethyl-4-nitroindole

[0156] Dissolve p-nitrophenylhydrazine, 3-methyl-2-butanone, and anhydrous sodium acetate at a molar ratio of 1:1.1:1.5 in acetic acid, and react under reflux and stirring for 8 hours. The reaction solvent was removed by rotary evaporation, and then a mixed solution of water and methanol with a volume ratio of 9:1 was added to dissolve the remaining substances. The resultant was filtered, and then exposed to crystallization at room temperature for 48 hours to obtain crystal 2,3,3-trimethyl-4-nitroindole.

Embodiment 2

[0157] Embodiment 2 synthetic compound 53

[0158] Compound 53 was synthesized according to the following route:

[0159]

[0160] 1) Synthesis of 2,3,3-trimethyl-1-(butane)-nitroindole

[0161] The 2,3,3-trimethyl-nitroindole and 4-bromobutane obtained in Example 1 were added into the reactor at a molar ratio of 1:1.5, and the reactor was sealed and then evacuated to 10 Pa. 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.

[0162] 2) Synthesis and purification of compound 53

[0163] 2-Chloro-1-formyl-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...

Embodiment 3

[0165] Embodiment 3 synthetic compound 26

[0166] Compound 26 was synthesized according to the following route:

[0167]

[0168] 1) Synthesis of 2,3,3-trimethyl-1-(p-methylbenzoic acid)-nitroindole

[0169] In the reactor, add the 2,3,3-trimethyl-nitroindole and p-bromomethylbenzoic acid obtained in Example 1 with a molar ratio of 1:1.5, and vacuumize the reactor to 20Pa after sealing . 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.

[0170] 2) Synthesis and purification of compound 26

[0171] Add 2,3,3-trimethyl-1-(p-methylbenzoic acid)-nitroindole molar ratio of 1:2.5 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. Petro...

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Abstract

The invention discloses a heptamethine nitro indocyanine dye, a preparation method and application thereof, and belongs to the field of polymethine indocyanine dyes and preparation thereof, wherein the structural formula of the heptamethine nitro indocyanine dye is represented by a formula (I). The preparation method comprises the following steps: 1) carrying out a heating reaction on raw materials containing a 2,3,3-trimethyl-nitroindole 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. The dye has near-infrared light absorption and fluorescence development properties, and can be used as a probe auxiliary agent; and the preparation method has the advantages of short synthesis route, environment-friendly solvent, simple process, avoidance of noble metal catalysis, high yield, high 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 heptamethine nitroindole cyanine dye and the preparation method and application of the dye, belonging to the field of polymethine indole 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 ...

Claims

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Application Information

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IPC IPC(8): C09B23/08C07D209/10C09K11/06G01N21/64A61K49/00
CPCA61K49/0032C07D209/10C09B23/0066C09B23/08C09K11/06C09K2211/1007C09K2211/1029G01N21/643
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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