Dual brain-targeted prodrug with organic-amine-modified vitamin C being carrier
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A technology of vitamins and organic amines, applied in the field of medicine, can solve problems such as low therapeutic concentration, low permeability, and physical hazards
Active Publication Date: 2016-06-08
SICHUAN UNIV
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However, due to the low permeability of ibuprofen, the distribution in the CNS is limited, and the effective therapeutic concentration is low. In order to achieve a better therapeutic effect, the dose of the drug needs to be increased to make the drug reach a higher concentration in the body, but with At the same time, the drug conce...
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Embodiment 1
[0019] Preparation of compound 1
[0020]
[0021] Add acetyl chloride (0.4ml, 5.7mmol) to the suspension of vitamin C (L-Ascorbicacid) (20g, 114mmol) in acetone (re-distilled, 150ml), stir at room temperature for 20h; filter the reaction solution, wash the filter cake with cold acetone, The filter cake was dried to obtain white solid 1 (18 g), yield 73.3%. m.p.: 202-204°C.
Embodiment 2
[0023] Preparation of compound 2
[0024]
[0025] Xiang 1 (6g, 27.75mmol), K 2 CO 3 Add redistilled acetone (100ml) to the powder (11.3g, 81.5mmol), raise the temperature to reflux, add BnBr (8.74ml, 73.6mmol) to the suspension, after 4.5h, remove the solvent under reduced pressure, and add a small amount of water in turn , diethyl ether, a white solid was precipitated, filtered, and the filter cake was washed with cold water and cold diethyl ether; the filter cake was dried to obtain a white solid 2 (4.85g), with a yield of 44.1%.
Embodiment 3
[0027] Preparation of compound 3
[0028]
[0029] CH to 2 (4.85g, 12.23mmol) 3 CN (200ml) solution was added with HCl solution (20ml, 2mol / L), and the reaction was stirred at an external temperature of 30°C for 3h. The solvent was spun off, EA was added, washed twice with water, twice with saturated saline, and washed with anhydrous Na 2 SO 4 Drying and concentration gave yellow oil 3 (4.4g), yield 100%, and then slowly solidified into a white solid. m.p.: 67-69°C.
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Abstract
The invention discloses a dual brain-targeted prodrug with an organic-amine-modified vitamin C being a carrier. The dual brain-targeted prodrug is a structure or pharmacy acceptable salt or water compound shown in the general formula (I), wherein X represents -(CH2)n-, -C(O)-(CH2)n-C(O)-or-(CH2)m-O-, -(CH2)m-NH-, -(CH2)m-C(O)-, -c(o)-(ch2)M-, -C(O)-(CH2)m0NH-, n represents 0-6, m represents 1-4, and Drug represents medicine acting on the central nervous system. The series of prodrug can improve brain-targeted performance of the medicine and increase the concentration of the central nervous system, in this way, the treatment effect of the medicine is improved, meanwhile, medicine distributed on peripheral organs is reduced, and toxic and side effects of the medicine are reduced.
Description
technical field [0001] The invention relates to a class of novel compounds, in particular to the design, preparation and preliminary targeting determination of a class of dual brain-targeting prodrugs with organic amine-modified vitamin C as a carrier. It belongs to the field of medical technology. Background technique [0002] According to statistics, about 1 / 5 of the world's population suffers from various types and degrees of central nervous system (CNS) diseases, including brain tumors, acute or chronic pain syndrome, epilepsy, encephalitis, cerebral ischemia and neurodegeneration Diseases (e.g. Alzheimer's, Parkinson's, etc.). As the world's population ages, this trend will intensify and have serious implications for human health. The existence of the blood-brain barrier (BBB) has a certain protective effect on the human central nervous system, but it also restricts many substances from entering the brain from the blood. Almost all macromolecules and 95% of small m...
Claims
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