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Uses of 2,5-dewatering-D-glucitol and the like in preparing cancer treatment medicament

A technology of glucitol and gluconic acid is applied in the field of preparing medicines for the treatment of cancer, and can solve problems such as cell damage and adverse reactions

Inactive Publication Date: 2009-04-08
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the lack of selectivity for tumor cells, damage is also done to normal cells, causing serious adverse reactions

Method used

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  • Uses of 2,5-dewatering-D-glucitol and the like in preparing cancer treatment medicament
  • Uses of 2,5-dewatering-D-glucitol and the like in preparing cancer treatment medicament
  • Uses of 2,5-dewatering-D-glucitol and the like in preparing cancer treatment medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 Preparation of 2,5-anhydro-D-glucitol

[0032] Dissolve 5.0 grams of 2,5-anhydro-4,5-diacetyl-D-glucitol (for preparation, refer to Azeez M. Mubarak and Daniel M. Brown. J.C.S. Perkin I. 1982, 809-813) in 50 mL of methanol Add 1molL dropwise under ice-water bath -1 10 mL of sodium methoxide in methanol. After stirring at room temperature for 24 hours, it was adjusted to neutrality with a strong cationic resin. The resin was filtered off, washed three times with methanol, the filtrates were combined, concentrated under reduced pressure, and subjected to flash silica gel column chromatography (dichloromethane:methanol=10:1) to obtain 1.7 grams of 2,5-anhydro-D-glucitol, yield: 84.2 %. Its H NMR spectrum is consistent with that reported in the literature (J.Org.Chem.2000, 65, 5632-5638).

Embodiment 2

[0033] Example 2 Preparation of 2,5-anhydro-1-deoxy-D-glucitol

[0034] 5.0 grams of 2,5-anhydro-1-p-toluenesulfonyl-4,5-diacetyl-D-glucitol (preparation can refer to Azeez M.Mubarak and Daniel M.Brown.J.C.S.Perkin I.1982,809-813 ) was dissolved in 30 mL of DMSO, and then 1.4 g of sodium borohydride was added. Stir at about 70°C for 6 hours, then cool, pour the reaction solution into 150mL ice water, extract with ether (40mL×4), wash with saturated brine, anhydrous Na 2 SO 4 Drying, concentration under reduced pressure, and flash silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) yielded 2.5 g of 2,5-anhydro-1-deoxy-4,5-diacetyl-D-glucitol, Yield: 73.5%. 1 H NMR (300MHz, CDCl 3 )δppm: 1.37-1.39 (d, 3H), 2.70 (s, 1H), 4.21-4.30 (m, 3H), 4.59-4.66 (m, 3H), 5.21-5.22 (m, 3H), 7.40-8.07 ( m, 10H); ESI MS m / z: 379.1 [M+Na] + .

[0035] Dissolve 2.5 grams of 2,5-anhydro-1-deoxy-4,5-diacetyl-D-glucitol from the previous step in 25 mL of methanol, and add 1...

Embodiment 3

[0036] Example 3 Preparation of 2,5-anhydro-D-gluconic acid

[0037] Dissolve 5 g of 2,5-anhydro-3,4,5-tribenzyl-D-glucitol (refer to Carbohydrate Research, 171, 1-11; 1987) in 30 mL of DMF, and add 15 grams of pyridinium dichromate (PDC). After stirring vigorously at room temperature for 24 hours, the reaction solution was poured into 150 mL of ice water, extracted with ethyl acetate (40 mL×4), washed with saturated brine, anhydrous Na 2 SO 4 Drying, evaporation to dryness, and flash silica gel column chromatography (petroleum ether: ethyl acetate = 2:1) gave 3.8 g of 2,5-anhydro-3,4,5-tribenzyl-D-gluconic acid, yield: 73.6%.

[0038] Dissolve 3.8 grams of 2,5-anhydro-3,4,5-tribenzyl-D-gluconic acid from the previous step in 50 mL of ethanol, add 0.5 grams of 10% palladium carbon, and hydrogenate at room temperature and pressure for 48 hours. After the reaction was complete, the palladium carbon was removed by filtration, and the filtrate was evaporated to dryness. Silica...

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PUM

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Abstract

The invention discloses novel application of 2, 5-dehydrated-D-glucitol and an analogue thereof in the preparation of medicaments for treating cancer. The 2, 5-dehydrated-D-glucitol, 2, 5-dehydrated-1-deoxy-D-glucitol and 2, 5-dehydrated-D-gluconic acid can significantly inhibit and kill tumor cells.

Description

Technical field: [0001] The present invention relates to the use of 2,5-anhydro-D-glucitol and its analogs in the preparation of medicines for treating cancer. Background technique: [0002] 2,5-anhydro-D-glucitol (2,5-anhydro-D-glucitol) is a natural plant toxin isolated from the fungal pathogen Fusarium solani (Mart.) Sacc.NRRL18883, which can cause some species of plants Growth inhibition, necrosis and chlorosis (Tanaka et al., 1996). Its possible mechanism of action is: 2,5-anhydro-D-glucitol is phosphorylated by hexokinase and fructokinase in plants to 6-phosphate-2,5-anhydro-D-glucitol (AhG-6- P) and 1,6-bisphosphorylated 2,5-anhydro-D-glucitol (AhG-1,6-bisP); AhG-1,6-bisP competes with 1,6-bisphosphate for the binding site Inhibits aldolase, thereby causing plant cell death (J BIOSCIENCE 2002, 57, 645-653). [0003] In the prior art, 2,5-anhydro-D-glucitol has the activity of inhibiting plant growth and reducing blood sugar concentration in human body. But there i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/341A61P35/00
Inventor 孙宏斌牛犇柳军吴晓明
Owner CHINA PHARM UNIV
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