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Method for preparing benzo-phenoselenazine photosensitizer

A photosensitizer, benzophene technology, applied in the field of preparation of new photosensitizer benzophene selenazine derivatives

Inactive Publication Date: 2013-08-14
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic route has harsh reaction conditions, high equipment requirements, cumbersome steps, low yield, and great potential safety hazards

Method used

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  • Method for preparing benzo-phenoselenazine photosensitizer
  • Method for preparing benzo-phenoselenazine photosensitizer
  • Method for preparing benzo-phenoselenazine photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation of nano-copper oxide

[0035] CuSO 4 +NaOH+NaCO 3 → Cu 2 (OH) 2 CO 3 →CuO+H 2 O+CO 2

[0036] Prepare 1mol·L -1 CuSO 4 Aqueous solution, 1mol L -1 NaOH aqueous solution, 0.5mol L -1 NaCO 3 aqueous solution, add CuSO in a beaker 4 100mL each of aqueous solution and NaOH aqueous solution. At this time, a blue flocculent precipitate is formed, and then Na 2 CO 3 Aqueous solution 260mL, the reaction produces Cu 2 (OH) 2 CO 3Precipitation, vacuum filtration, the obtained precipitation was washed several times with deionized water, until there was no SO in the filtrate with barium chloride solution. 4 2- , the precipitate was dried in an oven at 90°C for 3h, then ground, and calcined in a muffle furnace at 350°C for 4h to obtain black CuO powder.

Embodiment 2

[0037] Embodiment 2: the preparation of two-(3-N, N-diethylaminophenyl) diselenium

[0038]

[0039] In a 100mL round bottom flask, mix 2g (7.2mmol) of 3-iodo-N, N-diethylaniline, 1.2g (15mmol) of copper oxide powder, 1.15g (14.5mmol) of selenium powder, 0.81g (14.5mmol) of potassium hydroxide ) and dimethyl sulfoxide 20mL, the solid was completely dissolved and reacted overnight at 110°C under the protection of argon, cooled to room temperature, adding 30mL of mixed solvent of water and ethyl acetate (volume ratio: 1:1) to the reaction flask, and using Separate the organic phase and the aqueous phase with a 250mL separatory funnel, extract the aqueous phase three times with ethyl acetate, combine the organic phases, wash twice with saturated NaCl solution, and add anhydrous NaCl after the organic phase is clear and free of oily substances. 2 SO 4 After drying, the solvent was distilled off under reduced pressure to obtain 2.36 g of a light red liquid with a yield of 71%. ...

Embodiment 3

[0041] Embodiment 3: Preparation of two-(3-N, N-diethylamino-6-nitrosobenzene) diselenium

[0042]

[0043] Under ice bath, 2.36g (5.2mmol) of the diselenium product obtained in the previous step was dissolved in 1mol L -1 In 200mL of hydrochloric acid, slowly add 0.72g (11.4mmol) of saturated aqueous solution of sodium nitrite, the solution slowly turns from yellow to orange during the dropwise addition, and a precipitate is formed, NaNO 2 After the solution was added dropwise, it was stirred for 10 min to complete the reaction. Filtration, the filtrate was extracted with dichloromethane (3 × 100mL), the organic layers were combined, washed twice with saturated NaCl solution, anhydrous NaCl 2 SO 4 After drying, the solvent was distilled off under reduced pressure, and the obtained yellow-brown crude product was recrystallized from isopropanol to obtain 1.84 g of orange powdery solid with a yield of 70%.

[0044] 1 H NMR (CDCl 3 , 400MHz, ppm) δ8.38(d, J=9.6Hz, 2H), 7....

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Abstract

The invention relates to a method for synthesizing 5-(alkylamide-)-9-(N, N-dialkylamide) benzo-phenoselenazine hydrochloride shown in a formula I by using nanometer copper oxide as a catalyst. A benzo-phenoselenazine derivant, namely the 5-(alkylamide-)-9-(N, N-dialkylamide) benzo-phenoselenazine hydrochloride is an excellent photosensitizer for a photodynamic therapy, has the absorption wavelength above 650 nanometers, good water solubility, larger absorption intensity, high tumor cell selectivity and short metabolic time and is easy for synthesis and structure modification, thereby being an ideal novel photosensitizer. The method comprises the following steps of: with 3-iodo-N,N-dialkylaniline and selenium powder as raw materials, preparing di-(3-N,N-dialkylaniline) diselenide shown in a formula II under the catalysis of copper oxide, carrying out a nitrosation reaction on the bi-(3-N,N-dialkylaniline) diselenide and sodium nitrite to generate a bi-(3-N, N-dialkylamide-6-nitrosobenzene) diselenide, and finally carrying out a cyclization reaction on the bi-(3-N,N-dialkylamide-6-nitrosobenzene) diselenide and N-alkyl-1-naphthylamine to prepare the benzo-phenoselenazine derivant shown in the formula I. The method for synthesizing the benzo-phenoselenazine derivant is mild in reaction conditions, simple to operate and high in yield; and the raw materials are available.

Description

technical field [0001] The invention relates to the technical field of synthesis of phototherapy drugs, in particular to a method for preparing novel photosensitizer benzophenaselenazine derivatives by using nano-copper oxide as a catalyst. Background technique [0002] Cancer is one of the major diseases that threaten human life. Radiotherapy and chemotherapy, as clinical adjuvant treatments after surgery, have relatively large side effects and cannot be used repeatedly. Photodynamic therapy is a rapidly developing new therapy, which has become one of the most active research fields in tumor medicine in the world. Compared with traditional tumor treatment methods such as surgery, radiotherapy, and chemotherapy, photodynamic therapy has the advantages of less trauma, low toxicity, good selectivity, and repeatable treatment. [0003] Photodynamic therapy (Photodynamic Therapy) is referred to as PDT. Its working principle is: the photosensitizer is injected into the human bod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D293/10
Inventor 宋相志许靖
Owner CENT SOUTH UNIV
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