A kind of solanesyl thiosalicylic acid compound, its preparation method and application
A technology of solanesyl thiosalicylate and nesyl thiosalicylate, which is applied in the field of solanesyl thiosalicylic acid compounds, can solve the problems of limited anti-tumor activity and single chemical group structure, and achieve precise delivery Effect
Active Publication Date: 2020-06-23
HENAN UNIVERSITY
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Problems solved by technology
However, due to the single chemical group structure of this system (succinate), its antitumor activity is very limited, it is necessary to introduce new chemical groups (such as thiosalicylate group) to adjust its antitumor activity
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Embodiment 1
[0040]
[0041] (1) Synthesis of solanesyl bromide (SOL-Br)
[0042] Take 20.0 g (29 mmol) solanesol and dissolve it in 100 mL of anhydrous petroleum ether. After it is completely dissolved in a hot water bath at 40°C, add 2.6 mL of pyridine in an ice-water bath, and slowly add 3.6 mL of PBr dropwise under stirring. 3 (13 mmol) in 26 mL of petroleum ether. React in an ice-water bath for 3 hours. After the reaction, pour 100mL of distilled water into it, separate the organic phase, remove part of the solvent, take the upper layer of light yellow solution, and add saturated NaHCO at a volume ratio of 1:1. 3 The solution was washed until the pH value of the organic phase was 7-8, and then washed twice with saturated brine, anhydrous MgSO 4 Drying and cooling at 4°C-5°C, white crystals precipitated until the white crystals no longer increased, and a white powdery solid product was obtained after vacuum filtration, and vacuum-dried at 40°C to obtain a white product SOL-Br.
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The invention discloses solanesyl thiosalicylic acid compounds as well as a preparation method and application thereof, and belongs to the field of medicinal polymer materials and biological medicines. The structure formulae of the compounds are shown in the specification. Solanesol is used as a basic unit, the final product STS is obtained through two steps of bromination reaction and thioether bond introduction, and the reaction operation is simple, safe and effective. The successful synthesis of the target compound is confirmed through infrared spectroscopy and the characterization of nuclear magnetism, mass spectrometry and elemental analysis. Then solanesyl-based thiosalicylic acid is used as a hydrophobic skeleton, amphiphilic polymer materials with different structures are obtainedthrough covalent binding of ester bonds and hydrazone bonds through reaction with polyethylene glycol, DOX is loaded at the same time, and the amphiphilic polymer materials are applied to a drug delivery system. Nuclear magnetic characterization shows that the amphiphilic polymer materials are successfully prepared; it is proved that both the materials and the drug-loaded polymer have good anti-tumor effects.
Description
technical field [0001] The invention belongs to the field of medicinal polymer materials and biomedicine, and specifically relates to a class of solanesyl thiosalicylic acid compound, its preparation method and application. Background technique [0002] Solanesol, also known as nonaprenyl alcohol, is a terpene alcohol with 45 carbon atoms. As a natural compound, it widely exists in tobacco, potato and other Solanaceae plants. It is mainly used to synthesize complex compounds containing isoprene structure, such as CoQ10, Vk, etc. Solanesol has the functions of antibacterial, anti-inflammatory and ulcer treatment, and can effectively scavenge free radicals, so it has received extensive attention. [0003] Studies by Edward P. Serebryakov and others have shown that isoprene analogs (SDB) can significantly reduce the multidrug resistance of tumor cells and enhance the killing effect of drugs on cancer cells, so they can be used as a natural sensitizer. The structure is as foll...
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IPC IPC(8): C08G65/334C07C323/62C07C319/14A61K31/704A61P35/00A61K47/20A61K9/107
CPCA61K9/1075A61K31/704A61K47/20A61P35/00C07C323/62C08G65/3344C08G65/3348
Inventor 刘蕾侯甜熊瑶宋仕永
Owner HENAN UNIVERSITY