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Pyridine-containing BODIPY and quaternary ammonium salt photosensitizer thereof, and preparation method and applications of quaternary ammonium salt photosensitizer

A technology of fluoroborate dipyrrole and quaternary ammonium salts, which is applied in the field of drug synthesis, and can solve the problems of easy mutation of tumor cell growth, multidrug resistance of chemotherapy, and failure of chemotherapy, etc.

Active Publication Date: 2020-05-19
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the methods commonly used to treat malignant tumors include radiotherapy, chemotherapy, and surgical treatment. Studies have shown that because tumor cells have the ability to metastasize in the early stage, about 50% of patients with clinically diagnosed primary tumors have developed distant metastases, and Tumor cells grow fast and easily mutate, so multidrug resistance often occurs during chemotherapy, leading to chemotherapy failure; according to relevant statistics, more than 90% of them are related to multidrug resistance of tumor cells, and the antitumor drugs currently used in clinical practice Far from meeting the requirements of treatment

Method used

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  • Pyridine-containing BODIPY and quaternary ammonium salt photosensitizer thereof, and preparation method and applications of quaternary ammonium salt photosensitizer
  • Pyridine-containing BODIPY and quaternary ammonium salt photosensitizer thereof, and preparation method and applications of quaternary ammonium salt photosensitizer
  • Pyridine-containing BODIPY and quaternary ammonium salt photosensitizer thereof, and preparation method and applications of quaternary ammonium salt photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 synthetic compound 1

[0023] 1) Synthesis of 2-(2-(2-methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

[0024] 2g 2-(2-(2-methoxyethoxy)ethoxy)ethanol and 2.2g p-toluenesulfonic acid are dissolved in the mixed solution of 80mL dichloromethane and 80mL tetrahydrofuran, drop into 1.4mL triethylamine, argon Protected under gas, stirred at room temperature for 24 h, TLC monitored the completion of the reaction, evaporated THF and DCM under reduced pressure, added 150 ml each of ethyl acetate and water to shake the layers, extracted the aqueous layer with ethyl acetate, combined the organic layers, washed with saturated sodium chloride, Dry over anhydrous sodium sulfate, distill off the solvent under reduced pressure, and purify by column chromatography, PE:EA=1:4 elution gives the purified product 3.16g, yield 81.6%, MS (ESI) m / z ([M+H ] + ):319.1;

[0025] 2) Synthesis of 9-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-9H-carbazole

[0026] Dissolve 2.4 g of ca...

Embodiment 2

[0036] Embodiment 2 synthetic compound 2

[0037] Put 40 mg of compound 1 in a sealed tube, add 0.5 mL of iodomethane, and react at 60°C for 12 hours. After the iodomethane is completely volatilized, add a small amount of DCM to make it just dissolve, add methyl tert-butyl ether to precipitate a purple-black solid, suction filter, and dry , to obtain product 29mg, yield 65%, 1 H NMR (400MHz, CDCl 3 )δ8.68(s,1H),8.59(d,J=16.1Hz,2H),8.42(s,1H),8.35-8.34(m,2H),8.16-8.14(m,2H),8.05(s ,1H),7.89-7.87(m,2H),7.80-7.75(m,2H),7.58-7.56(m,2H),7.50-7.49(m,5H),7.26-7.25(m,2H),4.54 (s,7H),3.92-3.91(m,4H),3.54-3.53(m,4H),3.51-3.50(m,4H),3.46-3.65(m,4H),3.42-3.40(m,4H) ,3.32(s,6H),1.36(s,6H).

Embodiment 3

[0038] Embodiment 3: synthetic compound 3

[0039] 1) Synthesis of 1,3,5,7-tetramethyl-8-(3-pyridyl)-4,4'-difluoroborondipyrrole

[0040] 470 mg of 3-pyridinecarbaldehyde and 920 mg of 2,4-dimethylpyrrole were dissolved in 250 mL of dry DCM, a catalytic amount of TFA was added, protected by argon, and stirred at room temperature for 24 hours. Part of the DCM was distilled off under reduced pressure until the volume of the solution was 70 mL, 1.5 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone was added, protected by argon, and stirred at room temperature for 2 hours. Add 7 mL of triethylamine and 7 mL of boron trifluoride ether solution, under argon protection, stir overnight at room temperature, remove the solvent under reduced pressure, dissolve the residual solid in 150 mL of DCM, wash with water three times, dry over anhydrous sodium sulfate, evaporate under reduced pressure Remove the solvent, and purify DCM / PE=1 / 3 by column chromatography to obtain 195 mg of orange solid, ...

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Abstract

The invention belongs to the field of drug synthesis, and relates to a pyridine-containing BODIPY compound represented by a general formula (I), and a quaternary ammonium salt thereof, particularly toa pyridine quaternary ammonium salt photosensitizer, a preparation method and medical applications thereof. According to the invention, the results of in-vitro photosensitization efficiency and tumorcell inhibition activity tests show that the compound has good antineoplastic activity, can be further used for preparing new antineoplastic drugs, and is used for treating non-specific wide tumors such as gastric cancer, breast cancer, prostate cancer, lung cancer, colon cancer, bladder cancer, ovarian cancer, skin cancer and cervical cancer.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to a novel pyridine-containing fluoroborate dipyrrole and a quaternary ammonium salt photosensitizer, and a preparation method and application thereof. In particular, it relates to a pyridine-containing fluoroborate dipyrrole and a quaternary ammonium salt photosensitizer, a preparation method and a pharmaceutical application thereof. Background technique [0002] According to reports, malignant tumors have become a common disease that seriously endangers people's lives and health. According to incomplete statistics, there are about 20 million new cases in the world every year; in my country, there are about 1.6-2 million new cases and 1.3 million deaths each year. At present, the methods commonly used to treat malignant tumors include radiotherapy, chemotherapy, and surgical treatment. Studies have shown that due to the ability of tumor cells to metastasize in the early stage, about 50...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02A61K41/00A61P35/00
CPCC07F5/022A61K41/0057A61P35/00
Inventor 赵伟利董肖椿林光宇喻支梁
Owner FUDAN UNIV
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