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Muscone derivatives, preparation method and application thereof

A technology of muscone derivatives, applied in the field of preparation of muscone derivatives, can solve problems such as toxic and side effects, achieve good effects, improve brain targeting effect, and good elution effect

Active Publication Date: 2019-06-07
GUILIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of muscone’s aroma-enhancing effect to promote these drugs to pass through the BBB requires repeated use of muscone, and muscone metabolizes slowly in the brain, resulting in accumulation and certain toxic side effects

Method used

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  • Muscone derivatives, preparation method and application thereof
  • Muscone derivatives, preparation method and application thereof
  • Muscone derivatives, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Embodiment 1: the preparation of muscone derivative

[0078] The preparation method of muscone derivative, the reaction route that described preparation method involves is:

[0079]

[0080] The concrete reaction steps of above-mentioned reaction route are:

[0081] Step 1: Synthesis of Compound C2

[0082] While stirring, add 100 g (0.63 mol) of Br to the 500 mL methanol solution containing 100 g (0.42 mol) of muscone C1 2 , and the reaction was stirred overnight at room temperature, and the resulting mixture was washed with 300 mL of saturated Na 2 S 2 o 3 The solution was diluted and extracted three times with 300 mL of ethyl acetate, the combined extracts were washed successively with 300 mL of water and 300 mL of saturated NaCl aqueous solution, washed with anhydrous NaCl 2 SO 4 After drying and filtering, the filtrate was concentrated and spin-dried, eluted with petroleum ether, and the residue was purified by silica gel chromatography to obtain compound ...

Embodiment 2

[0094] Embodiment 2: Muscone phospholipid compound DSPE-PEG 2000 - Preparation of muscone

[0095] The muscone phospholipid compound DSPE-PEG of the present embodiment 2000 -The preparation method of muscone, comprises the steps:

[0096] Compound C6, DSPE-PEG obtained in Example 1 2000 -The mixture of NHS and triethylamine, according to the ratio of 8mg:1mL, was dissolved in the mixed solvent of chloroform and methanol, and reacted overnight with magnetic stirring at 30°C, and the reaction mixture was washed with 50mL water and 50mL saturated NaCl aqueous solution successively, and washed with Water Na 2 SO 4 After drying and filtering, the filtrate was concentrated and spin-dried, eluted with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 10:1, and the residue was purified by chromatography to obtain the muskone phospholipid compound DSPE-PEG 2000 - muscone, its structural formula is:

[0097]

[0098] Among them, the compound C6, DSPE-PEG...

Embodiment 3

[0100] Embodiment 3: Muscone phospholipid compound DSPE-PEG 2000 - Preparation of muscone

[0101] The muscone phospholipid compound DSPE-PEG of the present embodiment 2000 -The preparation method of muscone, comprises the steps:

[0102] Compound C6, DSPE-PEG obtained in Example 1 2000 -The mixture of NHS and triethylamine, according to the ratio of 8mg:1mL, was dissolved in the mixed solvent of chloroform and methanol, and reacted overnight with magnetic stirring at 30°C, and the reaction mixture was washed with 50mL water and 50mL saturated aqueous NaCl solution successively, and washed with free Water Na 2 SO 4 After drying and filtering, the filtrate was concentrated and spin-dried, eluted with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 10:1, and the residue was purified by chromatography to obtain the muskone phospholipid compound DSPE-PEG 2000 - muscone, its structural formula is:

[0103]

[0104] Among them, the compound C6, DSP...

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Abstract

The invention discloses muscone derivatives, a preparation method and an application thereof, belonging to the technical field of biological materials. The muscone derivatives have a structure as represented by formula (A) and (B) and pharmaceutically acceptable salts of that above structures. The invention also discloses the preparation method of the above muscone derivatives and the applicationthereof. Firstly, the muscone derivative of the present invention is easy to form hydrochloride and can improve the solubility thereof. Secondly, the active group amino group on the structure can be connected to the carrier material through chemical reaction. Thirdly, it can be modified on the surface of the carrier material as a target head, and only a small amount dosage is used for modificationto promote the drug-loaded nano-delivery system into the brain. Fourthly, that muscone derivativecan be used for preparing the muscone phospholipid compound, and the muscone phospholipid compound hasgood biocompatibility, has the advantage of promoting the delivery system to penetrate the blood-brain barrier, and can be used for preparing the brain-targeted delivery drug.

Description

technical field [0001] The invention relates to a muscone derivative, a preparation method and an application thereof, and belongs to the technical field of biomaterials. Background technique [0002] Modern research has found that the opening of the BBB of the blood-brain barrier is a physical process and does not damage the brain tissue when aromatic Chinese medicines (musketone, borneol, etc.) promote the opening of the blood-brain barrier. Muscone (Mus for short) is one of the active ingredients obtained by distilling musk from the dry secretion musk in the mature male sachet of the deer animal Moschusberezovskii Flerov or the original musk deer (Moschus moschiferus L). Named 3-methylpentadecanone, it is the main physiologically active substance of musk. Due to the scarcity of wild musk deer and the needs of society, through the efforts of researchers in recent years, it can be synthesized by artificial synthesis. [0003] The chemical formula of muscone is C 16 h 30...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/20C07C269/04C07C271/24C07C247/14C07C45/63C07C49/457C07F9/09
Inventor 齐娜谭相端奉建芳段文娟张尚前
Owner GUILIN MEDICAL UNIVERSITY
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