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A kind of anticancer prodrug molecule and its preparation method and targeting compound

A compound and molecular technology, applied in the field of anti-cancer prodrug molecules and their preparation methods and targeted compounds, can solve the problems of short biological half-life, high toxicity, economic loss, etc.

Active Publication Date: 2020-08-07
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, chemotherapy has become the main means of treating cancer in clinical practice. However, due to their high toxicity and low selectivity, many small drug molecules cause greater damage to normal cells and tissues, which brings a series of side effects. Ultimately limiting the clinical utility of a range of drug molecules
On the other hand, many popular anti-cancer drugs require frequent administration due to their short biological half-life, which not only brings economic losses, but also increases the continuous damage of the drugs to the normal body.

Method used

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  • A kind of anticancer prodrug molecule and its preparation method and targeting compound
  • A kind of anticancer prodrug molecule and its preparation method and targeting compound
  • A kind of anticancer prodrug molecule and its preparation method and targeting compound

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preparation example Construction

[0041] The embodiment of the present invention also provides a preparation method of an anticancer prodrug molecule, comprising:

[0042] The above-mentioned targeting compound is connected to the amino group or hydroxyl group of the anticancer active molecule to obtain the anticancer prodrug molecule.

[0043] Further, the active group is a hydroxyl group, and the preparation method includes:

[0044] React the -OH group of the targeting compound with triphosgene / phosgene to convert it into -OCOCl, and then combine -OCOCl with -NH in the anticancer active molecule 2 Or -OH group reaction.

[0045] The -OH group of the targeting compound reacts with triphosgene / phosgene and transforms into -OCOCl; when there is only -NH in the anticancer active molecule 2 When the group, -OCOCl and -NH 2 Group reaction; when there is only -OH group in the anticancer active molecule, -OCOCl reacts with -OH group; if there is -NH in the anticancer active molecule 2 or -OH group, the anti-can...

Embodiment 1

[0057] This embodiment provides a targeting compound whose structural formula is:

[0058]

[0059] In the formula, X is S or Se, R 1 , R 2 , R 3 At least one of them is an active group, and the active group includes any one of carboxyl, hydroxyl and amino.

[0060] Targeting compounds can be: One of them can also be other structural formula types; as long as the aforementioned general formula and limiting conditions are met.

[0061] Further, preferably R 1 and R 3 is hydrogen; R 2 selected from carboxyl, hydroxyl and amino groups. Then the general formula of the targeting compound is: One of.

Embodiment 2

[0063] The present embodiment provides an anticancer prodrug molecule (named S-Gem), its structural formula is:

[0064]

[0065] The reaction formula for preparing the anticancer prodrug molecule (S-Gem) is:

[0066]

[0067] Its preparation method is as follows:

[0068] S1. Dissolve the anticancer prodrug molecule gemcitabine Gem (1g, 3.8mmol) in 25mL of anhydrous DMF (dimethylformamide), add imidazole (0.78g, 11.5mmol) and TBDMSCl (tert-butyldimethylformamide) in sequence Chlorosilane) (1.5g, 9.6mmol); stirred at room temperature overnight, after the reaction was completed, the solvent was removed under reduced pressure, then extracted with ethyl acetate, the organic phase was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, and spin-dried , separated by silica gel column chromatography to obtain TBSGem.

[0069] S2. Under argon protection, 1mmol cyclopentylamine was added to 25mL of anhydrous dichloromethane, then p...

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Abstract

The invention discloses an anticancer prodrug molecule and its preparation method and a target compound, and relates to the field of organic synthesis and molecular medicine. The target compound of the anticancer prodrug molecule can be selectively identified by protein which is excessively expressed in a cancer cell; the preparation method of the anticancer prodrug molecule includes steps of connecting the target compound to amino acid or hydroxyl of the anticancer active molecule; through the method, the target compound is connected with the anticancer active molecule, thus the anticancer prodrug molecule is prepared; after the target compound is identified by the protein specificity which is highly expressed in the cancer cell, the anticancer prodrug molecule is released and directly acted on the cancer cells, thereby reaching the purpose of targeted treatment.

Description

technical field [0001] The invention relates to the fields of organic synthesis and molecular medicine, in particular to an anticancer prodrug molecule, a preparation method thereof and a targeting compound. Background technique [0002] Chemotherapy is the treatment of cancer cells by using chemotherapy drugs to kill cancer cells. Chemotherapy is currently one of the most effective means of treating cancer, together with surgery and radiotherapy, it is also known as the three major means of cancer treatment. [0003] At present, chemotherapy has become the main means of treating cancer in clinical practice. However, due to their high toxicity and low selectivity, many small drug molecules cause greater damage to normal cells and tissues, which brings a series of side effects. Ultimately, the clinical application of a series of drug molecules is limited. On the other hand, many popular anticancer drugs require frequent administration due to their short biological half-life...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/06C07H1/00C07D339/04C07D339/08C07D339/00C07D345/00A61P35/00
CPCC07D339/00C07D339/04C07D339/08C07D345/00C07H1/00C07H19/06
Inventor 房建国李新明
Owner LANZHOU UNIVERSITY
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