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Glaucocalyxin A acid ester derivative as well as preparation method and application of Glaucocalyxin A acid ester derivative

A technology of cylinate and cyanin, which is applied in the field of cyanin derivatives, can solve the problems of fast elimination, short half-life, and low polarity of GLA, and 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 objectives of the present invention is to provide a structurally improved cylindroic acid ester derivative with a good inhibitory effect on tumor cell lines, so as to solve the problem of GLA having small polarity, not easily soluble in water, short half-life, and excessive elimination in vivo. Fast and other defects, so as to be used as a drug for the treatment of cancer

Method used

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  • Glaucocalyxin A acid ester derivative as well as preparation method and application of Glaucocalyxin A acid ester derivative
  • Glaucocalyxin A acid ester derivative as well as preparation method and application of Glaucocalyxin A acid ester derivative
  • Glaucocalyxin A acid ester derivative as well as preparation method and application of Glaucocalyxin A acid ester derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Embodiment 1: the preparation of cyanine A

[0084] 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:

[0085] Step 1 is an extraction step, which further includes:

[0086] Step 1.1: Take fragrant tea and vegetable medicinal materials (aerial parts) and grind them to 20-50 mesh;

[0087] 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 80°C to 90°C for 1 to 2 hours, extract and filter to obtain the extract liquids and residues;

[0088] 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;

[0089] Step 1.4: Combine the extracts obtained in steps 1.2 an...

Embodiment 2

[0107] Example 2: Derivatization of succinic acid

[0108] according to figure 1 In the reaction equation shown, the cyanine A prepared in Example 1 is derivatized with succinic acid, thereby introducing a modified substituent into the cyanine A to obtain the succinate of cyanine A, The derivatization step 5 further comprises:

[0109] Step 5.1: Dissolve 0.96-1.16 g of succinin obtained in step 4 in 25-35 ml of tetrahydrofuran, and add 0.857-1.057 g of succinic acid and 0.067-0.087 g of DMAP in turn at room temperature, and stir the reaction at room temperature 10-14 hours;

[0110] Step 5.2: heating the reaction solution in step 5.1 to 40°C-50°C and distilling under reduced pressure to remove tetrahydrofuran;

[0111] Step 5.3: add 25-35ml of water to the reaction solution in step 5.2 to dilute, then extract 2-4 times with 25-35ml of ethyl acetate, combine the organic phases, wash with saturated brine, and dry over anhydrous sodium sulfate;

[0112] Step 5.4: Heat the was...

Embodiment 3

[0114] Example 3: Glycine derivatization

[0115] according to Figure 3a~3b As shown in the reaction equation, the succinate of cyanine A prepared in Example 2 is derivatized with glycine, thereby introducing a modified substituent into cyanine A to obtain the succinate of cyanine A. Derivatives of acid ester and glycine, the derivatization step 6 further comprises:

[0116] Step 6.1: Dissolve 113.5-133.5 mg of succinate of cerulein in 1-5 ml of tetrahydrofuran (THF), and dissolve 19.3-21.3 mg of N-hydroxysuccinimide (NHS) in 3-7 ml of phosphate buffer solution (PBS buffer solution);

[0117] The PBS buffer solution is 0.2 μmol / L and its pH=8.0;

[0118] Step 6.2: Add the obtained PBS solution of NHS dropwise to the THF solution of succinate A succinate at room temperature, stir and react at room temperature for 10 to 20 minutes, and then heat the obtained reaction solution to 30°C to 40°C °C, distilled under reduced pressure to remove THF to obtain a yellow oily crude pr...

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Abstract

The invention discloses a structure of a Glaucocalyxin A acid ester derivative as well as a preparation method and an application of the Glaucocalyxin A acid ester derivative in treating cancers. The molecular structure of the Glaucocalyxin A acid ester derivative has a general formula as shown in the specification, wherein R1 and R2 are succinic acid substituent-C4H5O4, glutaric acid substituent-C5H7O4M, glycine derivative substituent-C6H8NO5 of succinic acid, and glycine substituent-C7H10NO5 or glycine substituent-OH of glutaric acid. The preparation method has the following steps: in the presence of tetrahydrofuran and 4-dimethylamino pyridine, the extracted Glaucocalyxin A and succinic acid or glutaric acid are reacted to obtain the succinic acid ester or glutaric acid ester of the Glaucocalyxin A disclosed in the invention, and the Glaucocalyxin A acid ester derivative reacts with N-Hydroxysuccinimide and glycine in turn in the presence of a buffer solution of tetrahydrofuran and phosphate to obtain the derivative of the acid ester of the Glaucocalyxin A and the glycine disclosed in the invention.

Description

technical field [0001] The present invention relates to cyanine A (GLA) derivatives, in particular to glycocalycilin ester derivatives. The present invention also relates to the preparation method of the saliva carbinate 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-inflammatory activ...

Claims

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Application Information

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IPC IPC(8): C07C69/40C07C69/42C07C235/74C07C67/08C07C231/12A61K31/22A61P35/00
Inventor 李云森陈子珺程萍雷启福
Owner SHANGHAI JINHAO PHARMA DEV
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