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Tanshinone I derivatives and pharmaceutical application thereof

A technology for tanshinone and derivatives, applied in the field of medicine, can solve the problems of insufficient development of the medicinal value of tanshinone I, difficult structural modification of the molecular structure, etc. water soluble effect

Active Publication Date: 2006-09-27
JIANGSU CAREFREE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the unique molecular structure of tanshinone I is difficult to carry out structural modification. After a long period of research, Shanghai First Biochemical Pharmaceutical Co., Ltd. successfully synthesized sodium tanshinone I sulfonate in the early 1980s, which is mainly used for tanshinone II A reference substance for impurity inspection of sodium sulfonate API, the medicinal value of tanshinone I has not been fully developed

Method used

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  • Tanshinone I derivatives and pharmaceutical application thereof
  • Tanshinone I derivatives and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1. Hydrogen spectrum, mass spectrum and analysis of 2-formaldehyde-tanshinone I and 2-acrylic acid-tanshinone I after derivatization of tanshinone I.

[0021] 2-Formaldehyde-tanshinone I

[0022] MS m / z (%): 304 (M + ), 289 (M + -CH 3 )

[0023] 1 H-NMR (CDCl 3 ,) δ9.87(s, 1H), 9.25(d, 1H), 8.26(d, 1H), 7.98(d, 1H), 7.52(q, 1H), 7.32(d, 1H), 3.71(s, 2H), 2.65(s, 3H), 2.28(s, 3H).

[0024] 2-Acrylic acid-tanshinone I:

[0025] MS m / z(%): 346(M), 331(M + -CH 3 )

[0026] 1 H-NMR (DMSO-d 6 ,) δ12.63(s, 1H), 9.21(d, 1H), 8.32(d, 1H), 8.05(d, 1H), 7.61(q, 1H), 7.39(d, 1H), 7.22(d, 1H), 6.44(d, 1H), 3.65(s, 2H), 2.52(s, 3H), 2.15(s, 3H).

Embodiment 2

[0027] Embodiment 2,, the comparison of water solubility

[0028] compound

Embodiment 3

[0029] The synthesis of embodiment 3.2-sodium acrylate-tanshinone I:

[0030] (1). Synthesis of 2-formaldehyde-tanshinone I: Dissolve 6.93g tanshinone I in 150mL DMF, add 20mL phosphorus oxychloride dropwise at room temperature, stir for 2 hours, pour the reaction solution into 2000mL ice water, and a solid precipitates , filtered, the filter cake was washed to neutrality, dried, and the yield was quantified.

[0031] (2). Synthesis of 2-acrylic acid-tanshinone I: Dissolve 500mg of 2-formaldehyde-tanshinone I in 100mL of benzene, add 10mL of pyridine and 240mg of malonic acid in turn, heat to reflux to separate water, react for 10 hours, evaporate under reduced pressure Remove the solvent, add 50 mL of 5% sodium carbonate aqueous solution to the residue, filter, and adjust the pH of the filtrate to nearly 2 with concentrated hydrochloric acid, then a solid is precipitated, filter and dry to obtain a solid.

[0032] (3). Synthesis of 2-sodium acrylate-tanshinone I: 500mg 2-acr...

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Abstract

The invention discloses a tanshinoneIderivant and application in pharmacy, which is characterized by the following: the constitutional formula is showed in the diagram; when X is -(CHR)n-, R=H or alkyl with one to eight carbons, n=0-8; or X is -(CR=CH)n-, R=H or the alkyl with one to eight carbons, n=1-4. The derivant can be produced medicinal agent for clinical application.

Description

technical field [0001] The invention relates to a class of compound derivatives and their application in pharmacy, in particular to derivatives of tanshinone I and their application in pharmacy, belonging to the technical field of medicine. Background technique [0002] Salvia miltiorrhiza is the dry root and rhizome of Salvia miltiorrhiza Bge., a plant in the Labiatae family. It was first recorded in "Shen Nong's Materia Medica", and has been recorded in successive dynasties of herbal medicines. It is bitter in taste, slightly cold in nature, and enters the two meridians of Guixin and Liver. Tool dispelling blood stasis and relieving pain, promoting blood circulation to stimulate menstrual flow, clearing away heart-fire and eliminating troubles. Salvia miltiorrhiza is a traditional Chinese medicine for promoting blood circulation and removing blood stasis, and its commonly used preparations are mainly used to treat cardiovascular and cerebrovascular diseases. The chemical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/87A61K31/343A61K9/20A61K9/48A61K9/08A61K9/19A61P9/00A61P9/10A61P9/12A61P7/02A61P13/12A61P27/02A61P17/12
Inventor 秦引林
Owner JIANGSU CAREFREE PHARM CO LTD
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