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Nucleoside disulfide dinitrogen derivative and preparation method thereof

A technology of nucleoside disulfide and derivatives, which is applied in the field of synthesis of radiopharmaceutical-labeled precursor compounds, and can solve problems such as no relevant reports

Inactive Publication Date: 2010-12-29
JIANGSU INST OF NUCLEAR MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no registration number on CA, and there are no related reports at home and abroad

Method used

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  • Nucleoside disulfide dinitrogen derivative and preparation method thereof
  • Nucleoside disulfide dinitrogen derivative and preparation method thereof
  • Nucleoside disulfide dinitrogen derivative and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0032] Example 1 3', the synthesis of 5'-diacetylthymidine (product 2):

[0033] Take β-thymidine (2g, 8.26mmol), DMAP (0.1g) and join in 80mL dichloromethane solution, under the condition of ice-water bath, add dropwise the dichloromethane solution containing acetic anhydride (8mL) 20mL, dropwise finish, react The temperature of the solution was raised to 40°C, and the stirring was continued until the reaction solution was clear, and saturated NaHCO 3 Neutralize the excess acetic anhydride in the solution until no bubbles are produced, wash the organic phase with a large amount of water, anhydrous Na 2 SO 4 Dry, concentrate, pass through a silica gel column, the eluent is: ethyl acetate / petroleum ether=4 / 1 (v / v), the product obtained is recrystallized with ethyl acetate / petroleum ether to obtain 2.5 g of white crystals, the yield It is 92.84%, and the melting point is 124-126°C. Mass spectrum Ms (m / z): 349 (M+Na); 1 HNMR: CH at the 5th position of the pyrimidine ring 3 -...

Embodiment 2

[0034] Example 2 N 3 Synthesis of -tert-butoxycarbonyl-3',5'-diacetylthymidine (product 3):

[0035]Take 1.95g (5.98mmol) of product 2, dissolve it in 20mL of anhydrous tetrahydrofuran THF, add 2.7g (12.38mmol) of tert-butoxyformic anhydride, stir at room temperature for 80min, then add 4g (32.79mmol) of DMAP, and continue stirring at room temperature After 4 hours, evaporate the solvent to dryness, add 80 mL of ethyl acetate, then wash with water and dilute acetic acid respectively, dry the organic phase, evaporate to dryness and pass through the column, the eluent is ethyl acetate / petroleum ether=1 / 1 (v / v ), to obtain 2.5 g of white foamy solid, with a yield of 98.13%. Mass spectrum Ms (m / z): 449 (M+Na), 875 (2M+Na); 1 HNMR: Three CHs on tert-butyl 3 -1.55ppm (9H, singlet), CH at the 5th position of the pyrimidine ring 3 -1.88ppm (3H, single peak), CH of two acetyl groups 3 -2.105ppm (6H, singlet), CH at the 2-position of the pentose ring 2 -2.41ppm (2H, multiplet), CH...

Embodiment 3

[0036] Example 3 N 3 Synthesis of -tert-butoxycarbonyl-3',5'-bisacetyl-5-bromomethyl-2'-deoxyuridine (product 4):

[0037] Under the protection of nitrogen, the product 3 (1.0g, 2.3mmol) and a small amount of BPO (15mg) were dissolved in 100mL of dry carbon tetrachloride, and under light conditions, 0.38g (2.3mmol) of Br 2 Carbon tetrachloride solution 20mL, reflux reaction 3h, the temperature of the reaction solution is lowered to room temperature, carbon tetrachloride is evaporated to dryness by rotary evaporation, and the residue is passed through a silica gel column, and the eluent is ethyl acetate / petroleum ether=1 / 2(v / v) to obtain 0.48 g of white foamy solid, with a yield of 41.32%. Mass spectrum Ms (m / z): 527, 529 (M+Na); 1 HNMR: Three CHs on tert-butyl 3 -1.62ppm (9H, singlet), one acetyl CH 3 -2.08ppm (3H, singlet), one acetyl CH 3 -2.12ppm (3H, singlet), CH at the 2-position of the pentose ring 2 -2.41ppm (2H, multiplet), CH- at the 3rd position and CH at the ...

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Abstract

The invention discloses a nucleoside disulfide dinitrogen derivative and a preparation method thereof and belongs to the technical field of the synthesis of radiopharmaceutical labelled precursor compounds. The invention provides 5-{2-sulfydryl ethyl-[2-(2-sulfydryl ethyl amino) acetyl] amino}-methyl-2'-deoxyuridine (ANMdU) and a preparation method thereof, and is used for preparing technetium marked radiopharmaceutical 99mTc-ANMdU for tumor imaging. Test results show that the labelled rate of the ANMdU is greater than 95 percent, and the ANMdU has good in-vitro stability, rapid metabolism in normal mice and high safety of animal tests and is a potential tumor imaging agent.

Description

technical field [0001] A labeled precursor of technetium-labeled nucleoside analogs and a preparation method thereof, specifically relating to 5-{2-mercaptoethyl-[2-(2-mercaptoethylamino)acetyl]amino}-methyl-2' - Deoxyuridine (ANMdU) and a preparation method thereof, belonging to the technical field of radiopharmaceutical labeling precursor compound synthesis. Background technique [0002] 5-{2-Mercaptoethyl-[2-(2-Mercaptoethylamino)acetyl]amino}-methyl-2'-deoxyuridine (ANMdU for short), its molecular formula is C 16 h 26 N 4 o 6 S 2 , can conveniently form a stable complex with the isotope technetium 99m Tc-ANMdU. [0003] The most commonly used clinical tumor PET tracers are 18 F-FDG, its uptake depends in part on glucose transporters, which are overexpressed on tumor cells, and its maintenance on proliferating cells is a function of hexokinase regulation of glucose metabolism. However, 18 F-FDG is not a specific tracer for tumor imaging because glucose is also hi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/073C07H1/00
Inventor 陆春雄蒋泉福
Owner JIANGSU INST OF NUCLEAR MEDICINE
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