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Tanshinone class I derivant and synthesizing method and application thereof

A technology of tanshinone and derivatives, which is applied in the preparation of anti-tumor tanshinone I derivatives and its preparation field, and can solve the problems of difficulty in making dosage forms, low yield, low water solubility, etc.

Inactive Publication Date: 2012-10-03
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, at present, tanshinone compounds are obtained mainly through extraction and separation of natural tanshinone compounds in Danshen, and the following defects limit the research on the pharmaceutical activity of tanshinone compounds Its clinical application: 1. The extraction and separation of a single compound of tanshinone from natural plants requires the comprehensive use of multiple technologies such as adsorption, precipitation, extraction, ion exchange and chromatography. The yield is very low and the cost is too high
2. Most of the naturally occurring tanshinone compounds have extremely low water solubility and low bioavailability when taken orally; at the same time, it is difficult to make other suitable dosage forms
3. At present, the routes for synthesizing tanshinone compounds have problems such as high cost, harsh reaction conditions, long routes, and large environmental pollution.

Method used

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  • Tanshinone class I derivant and synthesizing method and application thereof
  • Tanshinone class I derivant and synthesizing method and application thereof
  • Tanshinone class I derivant and synthesizing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1 3-methoxy-8-methyl-1,4-phenanthrenedione

[0073] In the autoclave, add 2-methoxy-1,4-p-benzoquinone (0.5mmol) and o-methylstyrene (3mmol) in sequence, and add an appropriate amount of toluene to mix the two evenly, seal it, and do not apply external pressure , heated to 200°C, and stirred for 3h. TLC detects that the reaction is complete. The reaction liquid was cooled and separated by silica gel column, and the developing solvent was dichloromethane:petroleum ether (2:5). 59 mg of orange-red solid was obtained, and the yield was 65%. 1H NMR ( CDCl3, 400 Hz, TMS ): δ2.744 (s,3H), 3.942 (s,3H), 6.147(s,1H), 7.474(d,1H,J=6.8Hz), 7.628(t, 1H, J=16Hz), 8.224(d,1H, J=8.4Hz), 8.398(d,1H, J=9.2Hz), 9.401(d,1H, J=8.8Hz).

Embodiment 2

[0075] Example 2 3,6,7-trimethoxy-1,4-phenanthrenedione

[0076] The substrates were the corresponding styrene derivatives and 2-methoxy-1,4-p-benzoquinone to obtain 107.4 mg of an orange-red solid with a yield of 60%. 1H NMR ( CDCl3, 400 Hz, TMS ): δ3.920(s,3H,OCH3), 4.051(s,3H,OCH3), 4.110(s,3H,OCH3), 6.102(s,1H,AR-H) , 7.121(s,1H, AR-H), 7.952(d,1H, J=8.8Hz, AR-H), 8.11(d,1H, J=8.4Hz, AR-H), 9.145(s,1H, AR-H).

Embodiment 3

[0077] Example 3 3,6,-Dimethoxy-1,4-phenanthrenedione

[0078] The substrates were the corresponding styrene derivatives and 2-methoxy-1,4-p-benzoquinone to obtain 120.5 mg of an orange-red solid with a yield of 65%. 1 H NMR ( CDCl 3 , 400 Hz, TMS ): δ3.940(s,3H), 4.002(s,3H), 6.138(s,1H), 7.290(dd,1H,J=11.6Hz), 7.788(d,1H, J= 9.2Hz), 8.064(d,1H, J=8.0Hz), 8.116(d,1H, J=8.4Hz), 9.056 (d,1H, J=2.4Hz).

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Abstract

The invention relates to a tanshinone class I derivant and a synthesizing method and an application thereof, wherein the tanshinone class I derivant is characterized in that various substituent groups are introduced into different positions of a ring A of a tanshinone I molecule, the number of carbonyl groups on a ring C of the tanshinone I molecule is selectively retained, and a ring D of the tanshinone I molecule is reduced into a dihydrofuran ring. The preparation method comprises the steps that Diels-Alder reaction is carried out on a styrene compound and p-benzoquinone, and a key skeleton--phenanthraquinone compound is obtained after separation and purification; and then the phenanthraquinone compound is reacted with enamine to introduce a furan ring into the phenanthraquinone skeleton, and a target product--tanshinone class I compound is obtained through acidizing hydrolysis, oxidation reaction, separation and purification, and the tanshinone class I compound is catalytically hydrogenated to obtain a dihydro tanshinone class I compound. Cytotoxicity research and pharmacology research results show the cytotoxicity of the compound, so that the tanshinone compound has wide clinical application prospects, and is expected to be used as a new antineoplastic medicine.

Description

technical field [0001] The invention relates to the technical field of pharmacy, in particular to an anti-tumor tanshinone I derivative and its preparation method and application. Background technique [0002] Salvia miltiorrhiza is the dry root and rhizome of Salvia Miltiorrhiza Bunge (Salvia Miltiorrhiza Bunge), which was first recorded in "Shen Nong's Materia Medica", and has a long history of being used as medicine. Salvia miltiorrhiza is bitter in taste, slightly pungent, slightly cold in nature, returns to the heart and liver meridian, has the effects of dispelling blood stasis and relieving pain, promoting blood circulation to stimulate menstruation, nourishing blood to calm the nerves, cooling blood and reducing swelling. [0003] With the rapid development of technical methods such as chemistry and molecular biology, the research on the complex chemical components of the traditional Chinese medicine Salvia miltiorrhiza is also deepening. According to the existing r...

Claims

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Application Information

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IPC IPC(8): C07J73/00A61K31/58A61P35/00
Inventor 金辉李慧毛声俊马伟从陈叶桐刘诗雨
Owner SICHUAN UNIV
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