Dual-brain-targeting prodrug commonly modified by glucose and vitamin C
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A vitamin and glucose technology, applied in the field of medicine
Inactive Publication Date: 2018-04-13
SICHUAN UNIV
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Abstract
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Embodiment 1
[0023] Preparation of Compound 2
[0024]
[0025] NaH (24.0 g, 0.60 mol) was added to anhydrous DMF (300 ml) to form a suspension, and a solution of compound glucose 1 (15.0 g, 0.083 mol) in anhydrous DMF was added. After stirring for 30 min, BnBr (90 ml, 0.96 mol) was added dropwise under ice cooling, and after 10 min, it was stirred at room temperature for 24 h. Add 50 ml of methanol slowly, distill off DMF under reduced pressure, and use CH 2 Cl 2 (300 ml) to dissolve the residue, wash with saturated brine, and wash the organic layer with anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate to a yellow oil. Purified by column chromatography to obtain 46.1 g of white solid compound with a yield of 77.8%. Mp: 88-90°C. 1 H NMR (400MHz, CDCl 3 ) δ: 3.47-3.57 (m, 2H), 3.65 (t, 2H, J = 7.2 Hz), 3.74 (d, 1H, J =4.8 Hz), 3.77-3.80 (m, 1H), 4.52-5.02 (m, 11H), 7.13-7.41 (m, 25H).
Embodiment 2
[0027] Preparation of compound 3
[0028]
[0029] to molten ZnCl 2 (6.71 g, 49.30 mmol) was added AcOH-Ac 2 O (1:5, 75 ml), cooled to 0°C, added dropwise in Ac 2 Compound 2 (5.94 g, 9.42 mmol) in O (37 ml). Stir at room temperature for 1.5 h, add 200 ml of ice water, filter, and then dilute with CH 3 After OH recrystallization, 4.30 g of white solid was obtained, with a yield of 78.3%. Mp: 113-115°C. 1 H NMR (400 MHz, CDCl 3) δ: 2.05 (s, 3H), 3.48-3.58 (m, 3H), 3.66 (t, 1H, J = 8.8 Hz), 4.22-4.97 (m, 11H), 7.24-7.38 (m, 20H).
Embodiment 3
[0031] Preparation of Compound 4
[0032]
[0033] to CH 3 CH in ONa (0.47 g, 8.13 mmol) 3 Add compound 3 (8.50 g, 14.59 mmol) to OH (100 ml) solution, stir at room temperature for 5 h, add 200 ml of ice water and stir for 30 min, filter, and successively wash with saturated NaHCO 3 Wash with water and dry under vacuum to obtain 7.80 g of white solid with a yield of 98.9%. Mp: 104-106°C.
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Abstract
The invention discloses a dual-brain-targeting prodrug commonly modified by glucose and vitamin C; the dual-brain-targeting prodrug is the structure shown in a general formula (I) or pharmaceuticallyacceptable salts and aquo-complex; the formula is as shown in the specification. In which, X represents -(CH2)a , C(O) (CH2)a C(O) or (CH2)b O , (CH2)b NH , C(O) (CH2)b O , C(O) (CH2)b NH ; a represents 0-6, b represents 1-4; Y represents (CH2)n , C(O) (CH2)n C(O) or C(O) (CH2)m , (CH2)m C(O) ; n represents 0-6, m represents 1-4; Drug represents a drug applied to a central nerve system.A series of prodrug can improve the brain targeting property and pivot concentration, so as to enhance the drug effect; meanwhile, the drug distribution at a peripheral organ is reduced, and the toxic and side effects of the drug are reduced.
Description
technical field [0001] The invention relates to a class of novel compounds, in particular to the design, preparation, targeting and efficacy evaluation of a class of dual brain-targeted prodrugs based on glucose and vitamin C. 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 molecule drugs cannot effec...
Claims
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