A kind of dendritic compound containing porphyrin or chlorin and application thereof

A technology of chlorin and compounds, applied in the field of dendrimers, which can solve problems such as low solubility, limited application range of compounds, and insufficient selectivity of tumor cells

Active Publication Date: 2011-11-30
重庆乾鑫医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, at present, these compounds have low solubility under physiological pH conditions, insufficient absorption of red light in the phototherapy window, and insufficient selectiv...

Method used

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  • A kind of dendritic compound containing porphyrin or chlorin and application thereof
  • A kind of dendritic compound containing porphyrin or chlorin and application thereof
  • A kind of dendritic compound containing porphyrin or chlorin and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Its preparation method is as follows:

[0081]

[0082] 1. Preparation of compound (4):

[0083] Take compound (3) (28g, 19mmol), put it in a 1000ml round bottom flask, add 400mL of absolute ethanol, and then add Raney Ni prepared from 30g of nickel-aluminum alloy. Hydrogenation reaction at normal temperature and pressure. After the reaction was complete, Raney Ni was removed by filtration, and the solvent was evaporated by rotary evaporation to obtain 27 g of white solid. Yield 100%. m.p.: 180-181°C. LC-MS: M+1, 1440.3.

[0084] 2. Preparation of compound (5):

[0085] Get compound (4) (25g, 17mmol) and place in the round bottom flask, add 150mL toluene, Et 3 N (20 mL, 138 mmol) After compound (4) was completely dissolved, succinic anhydride (13.8 g, 138 mmol) was added. Heated to reflux for 12 hours. After the reaction, the solvent was evaporated by rotary evaporation, 200 mL of ethyl acetate was added, washed with 50 mL*4 saturated brine, and dried over anh...

Embodiment 2

[0091] Its preparation method is as follows:

[0092]

[0093]

[0094] 1. The preparation of compound (8):

[0095] Weigh compound (7) (30g, 136mmol), NaBH 4 (30g, 830mmol), placed in a three-necked flask, added 1000mL dry THF, stirred at room temperature for 30 minutes, added dropwise 240ml (CH 3 ) 3 SiCl (1.6mol), after the dropwise reaction was heated under reflux for 18 hours. The reaction solution was cooled, and water was added dropwise in an ice-water bath to quench the reaction. The solvent was evaporated, methanol was added to dissolve, and the filtrate was concentrated to obtain a viscous liquid, which was directly used for the next reaction.

[0096] 2. Preparation of compound (9):

[0097] Place the crude product of compound (8) obtained in the previous step reaction in a round bottom flask, add 300mL of methanol to dissolve, then add 60mL of triethylamine, dropwise add (Boc) 2 O (112 g, 0.45 mol). Stir at room temperature for 4 hours after dropping, ...

Embodiment 3

[0111] Its preparation method is as follows:

[0112]

[0113] 1. Preparation of compound (16):

[0114] Weigh compound (5) (3g, 1.95mmol), place in a round bottom flask and add 30mL THF, add compound (2) (83mg, 0.12mmol) after compound (5) dissolves completely, dicyclohexylcarbodiimide (DCC) (4.6g, 23mmol), 4-(N,N-dimethylamino)pyridine (DMAP) (0.8g, 5.85mmol) and p-toluenesulfonic acid (TsOH) (1.04g, 5.5mmol) were stirred at room temperature After 12 hours, the solid was removed by suction filtration, the filtrate was concentrated, and 30 mL of CH 2 CL 2 Then add 4.6g of DCC, 0.8g of DMAP, 1.04g of TsOH, stir the reaction at room temperature, stop the reaction after seven days, filter, and the filtrate is first washed with saturated NaHCO 3 solution (10mL*3), then washed with saturated NaCl solution (10mL*3), and then washed with anhydrous NaCl 2 SO 4 Drying and column chromatography (gradient elution: THF:PE=1:4, THF:PE=1:3, THF:PE=1:2) yielded 220 mg of the target ...

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PUM

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Abstract

The invention relates to a dendrimer containing porphyrin or chlorine and a pharmaceutically acceptable salt thereof shown in a general formula (I) or a general formula (II), wherein, A1 expresses ( in the instruction), or A1 (expresses in the instruction), the precondition that A2 which connects with A1 is meaningless, A2 expresses (in the instruction),and the invention also relates to a pharmaceutical composition with the inhibition effect to animal transplant tumors such as mice sarcoma 180 and the like, wherein, the effective curative dose of active components of the dendrimer containing porphyrin or chlorine and a pharmaceutical acceptable carrier are contained, and the invention also doscloses an application of an pharmaceutical composition containing the said active components in preparation of a medicinal preparation for improving and treating malignant tumor.

Description

technical field [0001] The invention relates to a dendrimer compound containing porphyrin or chlorin, a pharmaceutically acceptable salt and application thereof. Background technique [0002] Cancer is one of the most stubborn diseases in the world today, and scientists have been looking for safe and reliable treatments for it. Different from traditional surgery, chemotherapy, radiotherapy and other methods, photodynamic therapy (PDT) has attracted a lot of attention due to its superior characteristics such as effectiveness, safety, small side effects, synergy, reproducibility and relatively low cost. It uses the selective enrichment and photodynamic killing effect of specific photosensitizers in tumor tissues to cause directional damage to tumor tissues without affecting normal tissue functions. Its therapeutic window is light with a wavelength of 600-900nm. . [0003] As an integral part of photodynamic therapy, the research on photosensitizers has always been the focus ...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07F9/6561A61K31/409A61K31/6615A61P35/00
Inventor 李嘉和胡建兵王颖实
Owner 重庆乾鑫医药有限公司
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