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Podophyllotoxin compounds and their application and preparation process

A compound, podophyllotoxin technology, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve problems such as poor water solubility, strong drug resistance, and poor oral effect

Inactive Publication Date: 2009-06-24
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Tests have shown that podophyllotoxin drugs such as VP-16 have an effect on many tumor cells such as small cell lung cancer, non-Hodget's disease, acute monocytic leukemia, myelomonocytic leukemia, breast cancer, bladder cancer, and testicular cancer. Good therapeutic effect, but there are shortcomings such as strong drug resistance, poor water solubility, severe bone marrow suppression and poor oral effect. It is still an important task in the pharmaceutical industry to find new podophyllum drugs with good anti-tumor activity and small toxic and side effects. a hot spot of

Method used

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  • Podophyllotoxin compounds and their application and preparation process
  • Podophyllotoxin compounds and their application and preparation process
  • Podophyllotoxin compounds and their application and preparation process

Examples

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preparation example Construction

[0016] The preparation method of the compound of the present invention and the activity test results of the corresponding products are provided below

[0017] The preparation method of the present invention is: dissolving podophyllotoxin and N-(1-oxyl-2,2,6,6-tetramethylpiperidine-oxygen-carbonyl)-L-amino acid in dry dichloromethane , add a catalytic amount of N, N-lutidine, stir for 5 minutes under nitrogen protection, then add dicyclohexylcarbodiimide (DCC), stir and react for 2 hours under nitrogen protection, filter to remove the white precipitate, reduce After pressure evaporation to remove the solvent, the crude product was purified by column chromatography, eluting with dichloromethane-acetone with a volume ratio of 15:1 to obtain the compound of formula I.

[0018] For related reactions, see Reaction Scheme 1.

[0019]

[0020] Reaction 1

[0021] R in Formula 1 is hydrogen, methyl, methylthiomethylene, isobutyl or benzyl.

[0022] The N-(1-oxygen-2,2,6,6-tetrame...

Embodiment 1

[0031] 4α-4-L-glycine-N-(-formyl-2′,2′,6′,6′-tetramethylpiperidine-4′-nitroxyl ester)podophylloate (Ia) synthesis

[0032] Add 20ml of water and 20ml of methanol, 0.30g of sodium tungstate and 0.20g of edetate disodium salt into a 250ml Erlenmeyer flask, shake to dissolve, then add 10g of 2,2,6,6-tetramethyl- 4-Hydroxypiperidine, put it on a magnetic stirrer, start stirring, add 30% hydrogen peroxide in batches after dissolving, continue stirring, the solution turns from colorless to yellow, then gradually deepens, and finally becomes orange red, the reaction is about After 8-10 hours, distill methanol and most of the water under reduced pressure, add a small amount of sodium carbonate to shake the residual liquid after cooling, add sodium chloride for salting out, extract with ether 3-4 times, combine the extracts with anhydrous chlorination Calcium was dried, ether was removed under reduced pressure, and the solid was cooled to obtain 10.5 g of orange-red solid 2,2,6,6-tetr...

Embodiment 2

[0042] 4α-4-L-alanine-N-(-formyl-2′,2′,6′,6′-tetramethylpiperidine-4′-nitroxyl ester)podophylloate (Ib )Synthesis

[0043] The experimental procedure is the same as in Example 1, only alanine is used instead of glycine. The detection data of the product obtained by the reaction are as follows:

[0044] Yield: 90%; m.p.138-140°C; (c=0.5, CH 2 Cl 2 )IR(KBr)υcm -1 : 3344, 1781, 1716, 1485, 1507, 1589, 930, 1126, 1175, 1239, 1365; MS (FAB) m / z: 683 (M - , 30), 397(100); HRMS(ESI)C 35 h 43 N 2 o 12 : Theoretical value (M+2H), 685.2967, measured value, 685.2962.ESR: g 0 =2.0058, (3)ΔH PP =44.268Gs,A N =15.81Gs (three peaks at 1×10 -4 M, CH 2 Cl 2 )

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Abstract

The present invention relates to a new class of podophyllotoxin compounds, the use of this compound and the preparation method of this compound.

Description

technical field [0001] The present invention relates to a new class of podophyllotoxin compounds, the use of this compound and the preparation method of this compound. Background technique [0002] Podophyllotoxin (Podophyllotoxin) is a class of natural active substances with significant cytotoxicity mainly isolated from plants of the Berberidaceae Podophyllum genus, and a medicinal plant with a long history of application. For a long time, podophyllotoxins As a medicinal ingredient, it has been widely used to promote blood circulation and dissipate stagnation, insect bites, pain boils, swollen poison, bruises, rheumatic pain, vomiting, warts and bronchitis. Since the 1940s, King and Shliivan first reported that podophyllotoxin has colchicine-like effects (Stahelin H.F., Eur. J. Cancer, 1970, 6, 303), but its clinical application was limited for a period of time due to its toxic side effects. Afterwards, many chemists and pharmacologists modified its structure in order to o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04A61K31/4525A61P35/00C07D307/00C07D317/00
Inventor 刘映前田瑄
Owner LANZHOU UNIVERSITY
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