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Chlorinated glaucocalyxin A derivative and preparation method and application thereof

A technology for acyl chloride blue calyx A and derivatives is applied to the preparation of acyl chloride blue calyx A derivatives, the preparation of acyl chloride blue calyx A derivatives, and the application field in the treatment of cancer, and can solve the problem of excessive elimination, GLA Small polarity, not easy to dissolve in water, etc., to achieve a good inhibitory effect

Inactive Publication Date: 2011-03-30
SHANGHAI JINHAO PHARMA DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] One of the purposes of the present invention is to provide acyl chloride cyanine A (GLA) derivatives with good inhibitory effect on tumor cell lines and improved structure, so as to solve the problem of GLA having small polarity, not being easily soluble in water, and having a short half-life. Eliminate defects such as too fast in the body, so it can be used as a drug to treat cancer

Method used

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  • Chlorinated glaucocalyxin A derivative and preparation method and application thereof
  • Chlorinated glaucocalyxin A derivative and preparation method and application thereof
  • Chlorinated glaucocalyxin A derivative and preparation method and application thereof

Examples

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Embodiment 1

[0065] Embodiment 1: the preparation of cyanine A

[0066] Using fragrant tea herbs (aerial parts) as raw materials, through the steps of extraction, solvent treatment, resin treatment and recrystallization, to prepare cyanine (GLA), the specific process is as follows:

[0067] Step 1 is an extraction step, which further includes:

[0068] Step 1.1: Take fragrant tea and vegetable medicinal materials (aerial parts) and grind them to 20-50 mesh;

[0069] Step 1.2: Mix the obtained pulverized product with 95% ethanol (A.R.) at a volume ratio of 1:5 to 1:15, heat, reflux at a temperature of 80°C to 90°C for 1 to 2 hours, extract and filter to obtain the extract liquids and residues;

[0070] Step 1.3: Mix the residue obtained in step 1.2 with 95% ethanol (A.R.) at a volume ratio of 1:5 to 1:15, heat, reflux at 80°C to 90°C for 1 to 2 hours, extract and filter, To obtain the extract and the residue, repeat this step 1 to 3 times;

[0071] Step 1.4: Combine the extracts obtaine...

Embodiment 2

[0089] Example 2: Derivatization

[0090] according to figure 1 In the reaction equation shown, the cyanine prepared in Example 1 is derivatized with benzoyl chloride, thereby introducing a modified substituent into the cyanine to obtain a benzoyl chloride derivative of cyanine , the derivatization step 5 further comprises:

[0091] Step 5.1: Dissolve 90-110 mg of cyanine obtained in Step 4 in 3-7 ml of dichloromethane, and slowly add 41.5-51.5 mg of benzoyl chloride, 40.6- 50.6 mg of triethylamine and 3.1-4.1 mg of DMAP were stirred and reacted at room temperature for 12 hours;

[0092] Step 5.2: add 5-15ml of water to the reaction solution in step 5.1 to dilute, then extract 2-4 times with 5-15ml of dichloromethane, combine the organic phases, wash with saturated brine, and dry over anhydrous sodium sulfate;

[0093]Step 5.3: The organic phase washed and dried in step 5.2 was heated to 35°C-40°C and concentrated under reduced pressure to evaporate the solvent, and dried a...

Embodiment 3

[0095] Example 3: Derivatization

[0096] according to image 3 As shown in the reaction equation, the cyanine A prepared in Example 1 is derivatized with benzenesulfonyl chloride, thereby introducing a modified substituent into the cyanine A to obtain the benzenesulfonyl chloride derivative of cyanine A , the derivatization step 5 further comprises:

[0097] Step 5.1: Dissolve 90-110 mg of cyanine obtained in step 4 in 3-7 ml of dichloromethane, and slowly add 106.8-126.8 mg of benzenesulfonyl chloride, 86.3- 96.3mg of triethylamine and 6.2-8.2mg of DMAP were stirred and reacted at room temperature for 12 hours;

[0098] Step 5.2: add 5-15ml of water to the reaction solution in step 5.1 to dilute, then extract 2-4 times with 5-15ml of dichloromethane, combine the organic phases, wash with saturated brine, and dry over anhydrous sodium sulfate;

[0099] Step 5.3: The organic phase washed and dried in step 5.2 was heated to 35°C-40°C and concentrated under reduced pressure t...

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Abstract

The invention discloses a structure and a preparation method of a chlorinated glaucocalyxin A derivative, and application of the chlorinated glaucocalyxin A derivative to the treatment of cancer thereof. The general molecular structural formula of the chlorinated glaucocalyxin A derivative is shown below, wherein R1 is benzoyl chloride substituent(-C7H6O2), benzene sulfonyl chloride substituent(-C6H6O3S2) or -OH; and R2 is benzoyl chloride substituent(-C7H6O2), benzene sulfonyl chloride substituent(-C6H6O3S2) or -OH. The preparation method is to prepare the disclosed chlorinated glaucocalyxin A derivative by reacting the extracted glaucocalyxin A with benzoyl chloride or the benzene sulfonyl chloride in the presence of triethylamine and 4-dimethylamino pyridine.

Description

technical field [0001] The present invention relates to cyanine A (GLA) derivatives, in particular to acyl chloride cyanine A derivatives. The present invention also relates to the preparation method of the acyl chloride cyanocalin A derivative and its application in the treatment of cancer. Background technique [0002] Plants of the genus Lamiaceae. Widely distributed in East Asia and West Africa, there are about 150 species in the world, and about 90 species and 25 varieties in my country. Among them, about 30 kinds are used for medicinal purposes in the folk, and are used as medicines for clearing heat and detoxification, anti-cancer and anti-inflammatory, invigorating the spleen, promoting blood circulation, and killing bacteria. People have studied the mushroom components of this genus, and have extracted more than a hundred kinds of medicinal components from it. Pharmacological screening found that many diterpene compounds have cytotoxic, anti-tumor, and anti-infla...

Claims

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Application Information

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IPC IPC(8): C07C69/78C07C309/73C07C67/14C07C303/28A61K31/235A61K31/255A61P35/00
Inventor 李云森陈子珺程萍雷启福
Owner SHANGHAI JINHAO PHARMA DEV
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