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Preparation method of cholic acid-naphthalimide compound

A technology of naphthalimide and compound, which is applied in the field of novel cholic acid-naphthalimide anti-tumor compound and its preparation, can solve the problems of destroying the human immune system, gastrointestinal dysfunction, high recurrence rate, etc., and achieves the preparation method Economical, reduced toxicity, and high yield

Inactive Publication Date: 2014-07-02
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for solid tumors, which account for 90% of tumors, radiotherapy and chemotherapy are always difficult to cure the tumor. Not only the recurrence rate is very high, but also the normal cells are killed by radiotherapy and chemotherapy. Can cause gastrointestinal dysfunction, bone marrow suppression and other toxic and side effects, especially damage the human immune system

Method used

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  • Preparation method of cholic acid-naphthalimide compound
  • Preparation method of cholic acid-naphthalimide compound
  • Preparation method of cholic acid-naphthalimide compound

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0034] (1), preparation of compound 2

[0035] Dissolve 50 mmol of the compound propylenediamine or ethylenediamine in methanol solution with a mass fraction of 10% triethylamine, stir vigorously under ice bath, and add 20 mmol of di-tert-butyl dicarbonate solution in methanol dropwise , the dropwise addition was completed in half an hour. The reaction was naturally warmed to room temperature and stirred overnight. The reaction solution was milky white, and the solvent was evaporated under reduced pressure, and the residue was dissolved in chloroform and washed with saturated Na 2 CO 3 Wash with aqueous solution, dry over anhydrous sodium sulfate, filter, and distill off the solvent under reduced pressure to obtain a light yellow viscous oily liquid, which is mono-Boc-protected propylenediamine or ethylenediamine.

[0036] (2), preparation of compound 3

[0037] Dissolve 1.98g (10mmol) of 1,8-naphthalene dicarboxylic anhydride in 30mL of absolute ethanol, then add 1.74g (...

Embodiment 2

[0046] Embodiment 2: preparation compound 5a

[0047] 0.5 mmol of cholic acid was dissolved in 20 mL of anhydrous dichloromethane, then 0.162 g (1 mmol) of N,N-carbonyldiimidazole (CDI) was added and stirred. Then add 0.5 mmol of compound 4a, drop in 1 mmol of triethylamine, and react at room temperature. TLC detects the progress of the reaction. After the reaction was completed, 30 mL of dichloromethane was added to the reaction solution again, washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate, filtered, and separated by column chromatography (chloroform:ethanol volume ratio was 8:1) to obtain light yellow The solid is compound 5a.

Embodiment 3

[0048] Embodiment 3: preparation compound 5b

[0049] 0.5 mmol of deoxycholic acid was dissolved in 20 mL of anhydrous dichloromethane, then 0.162 g (1 mmol) of N,N-carbonyldiimidazole (CDI) was added and stirred for one hour. Then add 0.5 mmol of compound 4a, drop in 1 mmol of triethylamine, and react at room temperature. TLC detects the progress of the reaction. After the reaction was completed, 30 mL of dichloromethane was added to the reaction solution again, washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate, filtered, and separated by column chromatography (chloroform:ethanol volume ratio was 6:1) to obtain light yellow The solid is compound 5b.

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Abstract

The invention discloses a preparation method of a cholic acid-naphthalimide anti-tumor lead compound, belongs to the field of chemical synthesis of medicaments, and particularly relates to a synthesis method of a new naphthalimide compound with a chemical structural general formula shown in the specification. The preparation method of the compound is economical, simple, mild and effective. The obtained compound has extremely high inhibitory activity on HepG2 cells; and compared with phase-II clinic lead compound methylamphetamine, the compound partially has more superior inhibitory activity and can be used for preparing anti-tumor medicaments.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of novel cholic acid-naphthimide antitumor compounds and their preparation methods and applications. Background technique [0002] Malignant tumors seriously threaten human health, and humans have discovered malignant tumors for thousands of years. In terms of structure, function and metabolism, malignant tumor cells are very different from normal cells, and they have more than normal proliferation ability, which is not in harmony with the organism. At the same time, malignant tumor cells are also highly invasive and metastatic. [0003] At present, the main methods for treating malignant tumors include: surgical treatment, chemotherapy of anticancer drugs, radiotherapy, biological response modifiers and other treatments. The main methods are still traditional radiotherapy and chemotherapy. Radiation therapy is the use of radiation to kill cancer cells: that is, to b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J43/00A61P35/00
CPCY02P20/55
Inventor 赵永德马金飞代本才张豫黎霍萃萌陈瑨
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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