Anti-tumor drug compound, preparation method and application
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A technology of anti-tumor drugs and compounds, applied in the field of energy metabolism that inhibits anaerobic glycolysis process, can solve the problem of limited tumor suppression
Inactive Publication Date: 2016-05-04
JIANGSU UNIV
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However, 2-deoxyglucose cannot completely block the glycolysis of tumor cells, and the free mannose in tumor cells can be converted into glucose in the presence of mannose phosphate isomerase, thereby replenishing energy. Therefore, 2-deoxyglucose Tumor suppression is limited when used alone
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Embodiment 1
[0029] Embodiment 1 (best synthesis example)
[0030] 2-Deoxyglucose (78mg, 0.48mmol): Metformin hydrochloride (80mg, 0.48mmol), dissolved in 20mL methanol, nitrogen gas for 0.5h, 40°C for 3h, naturally cooled to room temperature after the reaction, and distilled off the solvent under reduced pressure , recrystallized from ethanol-ether (v / v-1:1), and dried in vacuo to obtain 140 mg of the product.
[0031] Molecular formula C 10 h 23 N 5 o 5 Elemental analysis: C, 40.83; H, 7.85; N, 23.75%. Ultraviolet UV-vis (CH 3 OH / nm)(ε×10 -4 ,dm 3 mol -1 cm -1 ):232(3.4).Infrared Spectrum IR(KBr,ν / cm -1 ):3371m, 3160m, 2900-2995m, 1628s, 1556s, 1468s, 1078s, 1007s, 710m, .600cm -1.
Embodiment 2
[0033] 2-deoxyglucose (248mg, 1.44mmol): metformin hydrochloride (80mg, 0.48mmol), wherein the molar ratio of 2-deoxyglucose to metformin hydrochloride is 3:1, dissolved in 10mL of methanol (the amount of 2-deoxyglucose substance and methanol The volume ratio is 1.44mmol: 10ml), blow nitrogen for 0.5h, and react at 10°C for 1h. After drying, 40 mg of the product was obtained, indicating that the yield of this synthetic scheme was lower than that of the best practice case.
Embodiment 3
[0035] 2-deoxyglucose (78mg, 0.48mmol): metformin hydrochloride (254mg, 1.44mmol), wherein the molar ratio of 2-deoxyglucose to metformin hydrochloride is 1:3, dissolved in 40mL of methanol (the amount of 2-deoxyglucose substance and methanol The volume ratio is 0.48mmol: 40ml), blowing nitrogen for 0.5h, reacting at 80°C for 6h, naturally cooling to room temperature after the reaction, distilling off the solvent under reduced pressure, recrystallizing from ethanol-ether (v / v-1:1), After vacuum drying, 70 mg of the product was obtained, which indicated that the yield of this synthetic scheme was lower than that of the best implementation case.
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Abstract
The invention discloses an anti-tumor drug compound, a preparation method and application, relates to synthesis of N-2-deoxyglucosyl dimethyldiguanide and the effect of N-2-deoxyglucosyl dimethyldiguanide on ATP inhibition and tumor resistance in lactic dehydrogenase and tumor cells, and belongs to the field of organic drugs. The preparation method comprises the steps that 2-deoxyglucose and metformin hydrochloride are mixed according to the mole ratio of 3:1-1:3, the mixture is dissolved into methyl alcohol, reacting is performed for 1-6 h in an oil bath at the temperature of 10 DEG C-80 DEG C under nitrogen protection, solvent is distilled off through reduced-pressure distillation, and recrystallization is performed to obtain the compound N-2-deoxyglucosyl dimethyldiguanide (2-DG-M for short). The novel compound N-2-deoxyglucosyl dimethyldiguanide is prepared by compounding 2-deoxyglucose and dimethyldiguanide, has the multiple effects such as the inhibition effect of lactic dehydrogenase and the ATP inhibition effect of the tumor cells and can serve as a novel anti-tumor compound to replace a current compound preparation of 2-deoxyglucose and dimethyldiguanide.
Description
technical field [0001] The invention relates to the synthesis of N-2-deoxyglucosyl metformin and its effect on the inhibition of lactate dehydrogenase and ATP in tumor cells and its anti-tumor effect, belonging to the field of organic medicines, in particular to a glycolysis inhibitor Preparation of compounds and their application in the field of energy metabolism inhibiting anaerobic glycolysis in tumor cells. Background technique [0002] Unlike normal cells, most tumor cells display a metabolic switch, called the "Warburg effect", from oxidative phosphorylation to glycolysis (Warburg, O. On the origin of cancer cells. Science 1956, 123, 309–314). This transition is very beneficial to tumor cells under hypoxic conditions. During this process, the glycolysis process provides sufficient energy for the survival of tumor cells. The resistance to chemotherapy has always been a difficult problem for oncologists (GranchiC, RoyS, GiacomelliC, MacchiaM, et al. -1612.). The lates...
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