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A kind of tripterine derivative and its preparation method and application

A technology of tripterycin and medicines, applied in the fields of tripteryne derivatives and their preparation and application, capable of solving the problems of high toxicity and poor water solubility of tripteryne

Active Publication Date: 2011-12-21
SUZHOU LEINA PHARMA RES DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, due to the disadvantages of poor water solubility and high toxicity of tripterygium, there has been no report of developing tripterygol into a new drug so far.

Method used

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  • A kind of tripterine derivative and its preparation method and application
  • A kind of tripterine derivative and its preparation method and application
  • A kind of tripterine derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: Preparation of tripterine cetyl alcohol ester

[0029] In a dry round bottom flask, add 32g tripterine, 14g DCC and 600mL CH 2 Cl 2 , add 19 g of n-hexadecanol dropwise in CH with stirring 2 Cl 2 (400mL) solution, reacted at room temperature for 24h. After the reaction was completed, 300 mL of H 2 O, with CH 2 Cl 2 Extraction, the organic phase was concentrated and evaporated to dryness. The product was separated by silica gel column chromatography to obtain 31 g of tripterine cetyl alcohol ester as a red solid with a yield of 65%.

[0030] The confirmed data of the chemical structure of tripterygium cetyl alcohol ester are as follows:

[0031] Molecular formula: C 45 h 70 o 4 (674)

[0032] 3432, 2922, 2855, 1800, 1739, 1606, 1550, 1516, 1437, 1383, 1286, 1184, 1129, 1082, 979, 847, 732, 573

[0033] 1 H-NMR (400MHz, CDCl 3 ): 7.03(s, 1H, 3-OH), 6.99(br d, J=7.00Hz, 1H, H-6), 6.53(d, J=0.84Hz, 1H, H-1), 6.28(d, J=7.00Hz, 1H, H-7), 3.49(s...

Embodiment 2

[0036] Embodiment 2: the preparation of tripterine cetyl alcohol ester

[0037] Add 32g tripterine and an appropriate amount of toluene in turn into a dry round bottom flask, add dropwise a toluene solution of 9.5g n-hexadecanol under stirring, and react at 110°C for 30 minutes. After the reaction was completed, an appropriate amount of H was added to the reaction solution. 2 O, with CH 2 Cl 2 Extraction, the organic phase was concentrated and evaporated to dryness. The product was separated by silica gel column chromatography to obtain 20.6 g of tripterine cetyl alcohol ester as a red solid with a yield of 43%.

Embodiment 3

[0038] Embodiment 3: the preparation of tripterine cetyl alcohol ester

[0039]Add 32g of tripterine, 10g of DCC and appropriate amount of carbon tetrachloride successively in a dry round bottom flask, add 12.6g of n-hexadecanol solution of carbon tetrachloride dropwise under stirring, and react at 0°C for 48h. After the reaction was completed, an appropriate amount of H was added to the reaction solution. 2 O, with CH 2 Cl 2 Extraction, the organic phase was concentrated and evaporated to dryness. The product was separated by silica gel column chromatography to obtain 27.8 g of tripterine cetyl alcohol ester as a red solid with a yield of 58%.

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Abstract

The invention provides tripterine long-chain alcohol ester and its preparation method and application. The tripterylide long-chain alcohol ester has significant prostate targeting, and has stronger antitumor and anti-inflammatory activities than tripteryne. Its structural formula is as follows: where n=10~20, m=2n+1, 2n-1, 2n-3, etc., wherein representative ones are n-hexadecanol, n-decyl alcohol, n-dodecyl alcohol, n-dodecyl alcohol, n- stearyl alcohol and oleyl alcohol.

Description

Technical field: [0001] The invention relates to a tripterine derivative and its preparation method and application. Background technique: [0002] Tripterygium wilfordii is a drug for treating autoimmune diseases, and it contains a variety of active ingredients, such as triptolide, triptolide, tripterine (Celastrol), etc. These active ingredients have complex effects on a variety of immune cells, including inhibiting proliferation, inducing apoptosis, and altering cytokine secretion. Tripterygium wilfordii is one of the main components of Tripterygium wilfordii, and its chemical structure is as follows: [0003] [0004] It has been reported in the literature that tripterygium has anti-inflammatory (including inhibition of COX2 activity, NF-kB, NO, leukotrienes, etc.), anti-tumor, anti-oxidation, anti-fungal, anti-hepatitis, insecticide, anti-malarial, contraceptive, anti-head Pharmacological activities such as dandruff, treatment of kidney disease, central nervous sys...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61P35/00A61P29/00
Inventor 刘珂关玉昆赵烽邵萌许辉翟大伟
Owner SUZHOU LEINA PHARMA RES DEV
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