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Anti-tumor compound with phototoxicity and preparation method and application thereof

An anti-tumor and phototoxic technology, applied in ruthenium organic compounds, platinum group organic compounds, anti-tumor drugs, etc., can solve the problems of complex and difficult clinical application of side effects, and achieve the effect of molecular stability, simple method, and good selectivity

Inactive Publication Date: 2018-11-06
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the frequent occurrence of serious side effects and drug resistance make clinical application complicated and difficult
However, dozens of anti-tumor drugs currently used in clinical chemotherapy or adjuvant therapy only have a good curative effect on the treatment of some tumors

Method used

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  • Anti-tumor compound with phototoxicity and preparation method and application thereof
  • Anti-tumor compound with phototoxicity and preparation method and application thereof
  • Anti-tumor compound with phototoxicity and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation method of the phototoxic antitumor compound of the present invention is:

[0035] S1, the RuCl of 350mg ruthenium weight content 37% 3 ·xH 2 O and 2.8mL of γ-terpinene with a purity of 95% were mixed and dissolved in 9mL of absolute ethanol, and the temperature was refluxed at 40°C for 6h, and the intermediate product (dichlorodimethylcumene dichloride combined diruthenium), the chemical formula of the intermediate product is:

[0036]

[0037] S2. Weigh 200 mg of 2-(4-piperidinyl) benzimidazole, then add 19 mL of carbon tetrachloride solvent, 0.8 mg of azobisisobutyronitrile, and 170 mg of N-bromosuccinyl Amine, reflux at 60°C for 20h, remove the solvent by rotary evaporation, then add 118mg of 6-bromoindazole and 31mg of the intermediate product, dissolve them in 14mL of anhydrous toluene, add 0.18mg of NaOH, 0.08mL of ethylenediamine, 2.8mg of cesium carbonate, 5.5mL of triethylamine, and then 30min of nitrogen, and then sequentially added 14.5m...

Embodiment 2

[0039] The preparation method of the phototoxic antitumor compound of the present invention is:

[0040] S1, the RuCl of 366mg ruthenium weight content 37% 3 ·xH 2 O and 3 mL of γ-terpinene with a purity of 95% are mixed and dissolved in 10 mL of absolute ethanol, and the temperature is refluxed for 6 h at 40° C., and the intermediate product (dichlorodimethylcumene dichloride) is separated out after standing. diruthenium), the chemical formula of the intermediate product is:

[0041]

[0042] S2. Weigh 201 mg of 2-(4-piperidinyl) benzimidazole, then add 20 mL of carbon tetrachloride solvent, 1 mg of azobisisobutyronitrile, and 177 mg of N-bromosuccinimide , reflux at 60°C for 24 hours, remove the solvent by rotary evaporation, then add 120 mg of 6-bromoindazole and 31.5 mg of the intermediate product, dissolve them in 15 mL of anhydrous toluene, add 0.2 mg of NaOH, 0.1mL of ethylenediamine, 3mg of cesium carbonate, 6mL of triethylamine, and then 30min of nitrogen, and t...

Embodiment 3

[0044] The preparation method of the phototoxic antitumor compound of the present invention is:

[0045] S1, the RuCl of 370mg ruthenium weight content 37% 3 ·xH 2O and 3.2mL of γ-terpinene with a purity of 95% were mixed and dissolved in 11mL of absolute ethanol, and the temperature was refluxed at 60°C for 8h, and the intermediate product (dichlorodimethylcumene dichloride combined diruthenium), the chemical formula of the intermediate product is:

[0046]

[0047] S2. Weigh 203 mg of 2-(4-piperidinyl) benzimidazole, then add 21 mL of carbon tetrachloride solvent, 1.2 mg of azobisisobutyronitrile, and 180 mg of N-bromosuccinyl Amine, reflux at 70°C for 26 hours, remove the solvent by rotary evaporation, then add 122 mg of 6-bromoindazole and 32 mg of the intermediate product, dissolve them in 15.5 mL of anhydrous toluene, and add 0.22 mg of NaOH under stirring conditions , 0.12mL of ethylenediamine, 3.2mg of cesium carbonate, 6.5mL of triethylamine, and then 30min of n...

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PUM

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Abstract

The invention provides an anti-tumor compound with phototoxicity, the chemical structural formula of which is shown in the description. The invention further discloses a preparation method and application of the anti-tumor compound with phototoxicity. The compound disclosed by the invention contains benzimidazole and indazole heterocycles, so the obtained compound has good bioactivity; and with alarge conjugated system, the molecules are more stable. The preparation method disclosed by the invention is simple, and has the advantage of low cost, the reaction process does not require a separation and purification process, raw material loss is reduced, and the requirement of green chemistry is met.

Description

technical field [0001] The invention relates to the technical field of compound preparation, in particular to a phototoxic antitumor compound and its preparation method and application. Background technique [0002] Cancer and malignancy are difficult-to-treat diseases characterized by high lethality. Despite tremendous efforts by scientific researchers to improve treatment, existing drugs have a relatively limited effective range of action, and there is a considerable need to develop new drugs and alternative therapies. Platinum-based antineoplastic drugs (such as cisplatin, carboplatin or oxaliplatin) are the most used at present, which have a significant influence and impact on current tumor chemotherapy. However, severe side effects and frequent occurrence of drug resistance make clinical application complicated and difficult. However, dozens of anti-tumor drugs currently used in clinical chemotherapy or adjuvant therapy only have a good curative effect on the treatmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00A61K31/555A61P35/00A61P29/00
CPCC07F15/0046A61P29/00A61P35/00
Inventor 李培源霍丽妮
Owner GUANGXI UNIV OF CHINESE MEDICINE
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