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Racemate Shikonin Naphthyme Nucleus Hydroxymethylated Sodium Sulfonate Derivatives

A technology for nuclear hydroxymethyl sulfonate sodium and racemate, which is applied in the field of racemic shikonin naphthyridine parent nucleus hydroxymethyl sulfonate sodium derivatives, and can solve the problems of limited application, poor solubility and the like , to achieve the effects of good anti-tumor activity, simple preparation method and novel structure

Inactive Publication Date: 2016-05-04
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these derivatives are extremely poorly soluble in water, which limits their application as antitumor drugs

Method used

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  • Racemate Shikonin Naphthyme Nucleus Hydroxymethylated Sodium Sulfonate Derivatives
  • Racemate Shikonin Naphthyme Nucleus Hydroxymethylated Sodium Sulfonate Derivatives
  • Racemate Shikonin Naphthyme Nucleus Hydroxymethylated Sodium Sulfonate Derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] This example relates to a 5,8-dimethoxy-6-(1'-acetoxy-4'-methyl-3'-pentenyl)-1,4 as shown in structural formula (I) - the preparation method of naphthoquinone-2-sodium sulfonate (I-1), such as figure 1 As shown, the following reaction steps are included:

[0019] Step 1, dissolve the racemate 1,4,5,8-O-tetramethylshikonin in anhydrous dichloromethane, add 1.5 times the equivalent (molar equivalent, the equivalent mentioned in the following are also equal molar equivalent) of acetic acid, 1.5 equivalents of N,N'-dicyclohexylcarbodiimide and catalytic amount of p-dimethylaminopyridine, stirred at room temperature until the racemate 1,4,5,8-O- Tetramethylshikonin disappeared; the precipitate generated during the reaction was removed by suction filtration. The filtrate was cooled to about 5°C, and an aqueous solution containing 3.0 times the equivalent of cerium ammonium nitrate was added dropwise with stirring, and the stirring was continued until the raw materials were ...

Embodiment 2

[0023] This embodiment relates to a 5,8-dimethoxy-6-[1'-(3-methylbutyryloxy)-4'-methyl-3'-pentenyl group having the structural formula (I) The preparation method of ]-1,4-naphthoquinone-2-sodium sulfonate (I-2), such as figure 1 shown, including the following steps:

[0024] The steps of this example are the same as those of Example 1, and in step one, acetic acid is replaced with 3-methylbutanoic acid. The product was a pale yellow oil with a total yield of 19%. 1 HNMR (400MHz,d 6 -DMSO): δ7.36(s, 1H, H-C(7)), 6.94(s, 1H, H-C(3)), 6.00(t, J=7.2Hz, 1H, H-C(1')), 5.12( d,J=6.0Hz,1H,H-C(3')),3.87(s,3H,OCH 3 ),3.77(s,3H,OCH 3 ),2.50(m,2H,H-C(2')),2.27(d,J=7.2Hz,2H,COCH 2 ),2.00(m,1H,CH),1.64(s,3H,C=CCH 3),1.52(s,3H,C=CCH 3 ),0.91(s,3H,CH 3 ),0.89(s,3H,CH 3 ).

Embodiment 3

[0026] This example relates to a 5,8-dimethoxy-6-[1'-(3,3-dimethylacryloyloxy)-4'-methyl-3'- The preparation method of pentenyl]-1,4-naphthoquinone-2-sodium sulfonate (I-3), such as figure 1 shown, including the following steps:

[0027] The steps of this example are the same as the steps of Example 1, in Step 1, acetic acid is replaced by 3,3-dimethacrylic acid. The product was a pale yellow oil with a total yield of 26%. 1 HNMR (400MHz, d 6 -DMSO): δ7.35(s,1H,H-C(7)),6.94(s,1H,H-C(3)),6.03(m,1H,H-C(1')),5.82(t,1H,J =1.2Hz,-COCH=),5.11(m,1H,H-C(3')),3.85(s,3H,OCH 3 ),3.76(s,3H,OCH 3 ),2.50(m,2H,H-C(2')),2.09(d,3H,J=1.2Hz,CH 3 ),1.90(s,3H,J=1.2Hz,CH 3 ), 1.64(s,3H,C=CCH 3 ),1.50(s,3H,C=CCH 3 ).

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Abstract

The invention discloses a racemic alkannin naphthazarin parent nucleus hydroxymethyl sodium sulfonate derivative. The structural formula of the derivative is shown as a formula (I) in the specification, wherein R is alkane, olefin or aromatic hydrocarbon having 1-6 carbon atoms. A preparation method of the compound is simple and convenient, the yield is high, and raw materials are readily-available. The prepared racemic alkannin naphthazarin parent nucleus hydroxymethyl sodium sulfonate derivative is novel in structure, and has high water solubility. As proved by in-vitro anti-tumor activity experiment research, the compound has high anti-tumor activity.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a racemic shikonin naphthalene naphthalene nuclei hydroxymethylated sodium sulfonate derivative. Background technique [0002] Comfrey is a commonly used clinical traditional Chinese medicine recorded in the Pharmacopoeia of the People's Republic of China. Comfrey can be divided into hard comfrey (also known as northeast comfrey, Lithospermumerythrohizon) and soft comfrey (also known as Xinjiang comfrey, A.euchromaJohnst). The main active ingredients in hard comfrey are shikonin and its derivatives, and soft comfrey contains arcanin and its derivatives. Shikonin and Akanin are enantiomers of each other, which have been proven to have anti-inflammatory, wound healing, antibacterial, antiviral, antithrombotic, antihyperthyroidism, antiimmune hypoxia, hypoglycemic, liver and liver protection and other biological activities. In recent years, research on the antitumor activity o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/32C07C309/44A61K31/222A61P35/00
Inventor 李绍顺宋化龙崔家华
Owner SHANGHAI JIAOTONG UNIV
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