2-(1',2',3'-triazole-4'-oxymethylenepyridine)-1,3,4,6-o-acetyl-d-glucose and its preparation method and application

A technology of oxymethylenepyridine and glucose, applied in 2‑(1',2',3'‑triazole‑4'‑oxymethylenepyridine)‑1,3,4,6‑O‑ Acetyl-D-glucose and its preparation and application fields can solve problems such as bone marrow suppression, gastrointestinal dysfunction, and lower quality of life of patients

Active Publication Date: 2018-01-05
HUBEI ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemotherapy and radiotherapy can kill normal cells as well as cancer cells, and can also cause side effects such as gastrointestinal dysfunction and bone marrow suppression, greatly reducing the quality of life of patients

Method used

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  • 2-(1',2',3'-triazole-4'-oxymethylenepyridine)-1,3,4,6-o-acetyl-d-glucose and its preparation method and application
  • 2-(1',2',3'-triazole-4'-oxymethylenepyridine)-1,3,4,6-o-acetyl-d-glucose and its preparation method and application
  • 2-(1',2',3'-triazole-4'-oxymethylenepyridine)-1,3,4,6-o-acetyl-d-glucose and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate, methanol as solvent, azide reagent as trifluoromethanesulfonyl azide.

[0026] Weigh compound 1 (4.313 g, 20 mmol) dissolved in triethylamine (7.5 mL, 54 mmol) and CuSO 4 .5H 2 O (50 mg, 0.2 mmol) in water (84 mL) was filled with nitrogen for protection, and then stirred continuously for 30 min under ice-water bath conditions. Compound 2 (5.030 g, 24 mmol) was added under constant stirring, and the reaction was continued for half an hour, then the ice-water bath was removed, and the system was allowed to react at room temperature for 24 hours.

[0027] TLC detection reaction. The solvent was evaporated under reduced pressure. The residue was azeotroped with 50 mL of toluene to remove water. After adding pyridine (100 mL, 20 mmol) to the above residue, Ac 2 O (15 mL, 160 mmol), stirred overnight. The solvent was distilled off under reduced pressure, and 50 mL of water was added to the residue....

Embodiment 2

[0028] Example 2: Synthesis of 4-pyridyl propargyl ether 7a, using tetrahydrofuran as solvent.

[0029] Weigh 4-pyridinemethanol (303 mg, 2.774 mmol) and dissolve it in dry tetrahydrofuran (2 mL). Then use nitrogen protection, ice water external bath, and stir for 30 minutes. Weigh NaH (133 mg, 3.329 mmol), add to the solution, and react for 30 minutes. Then 3-bromopropyne (413 mg, 3.472 mmol) was added. After continuing the reaction for 3 hours, 1 mL of water was added to quench the reaction in an ice bath. Extract with 100 mL of dichloromethane three times. Using TLC detection, the developer (PE: EA=4: 1) confirmed that the reaction was complete. Use silica gel column for purification, eluent (PE:EA=2:1). The product was subjected to vacuum distillation to remove the solvent, and finally the product 7a (151 mg, yield 37%) was obtained.

[0030] Example 3 Synthesis of 3-pyridine propargyl ether 7b, N, N'-dimethylformamide as solvent.

[0031] Weigh 3-pyridinemethanol (...

Embodiment 4

[0032] Example 4: Synthesis of 2-pyridine propargyl ether 7c, using acetonitrile as solvent.

[0033]Weigh 2-pyridinemethanol (300 mg, 2.74 mmol) and dissolve it in dry acetonitrile (5 mL). Then use nitrogen protection, ice water external bath, and stir for 30 minutes. Potassium carbonate (460 mg, 6.9 mmol) was weighed, added to the solution, and reacted for 30 minutes. Then 3-bromopropyne (413 mg, 3.472 mmol) was added. After continuing the reaction for 3 hours, 1 mL of water was added to quench the reaction in an ice bath. Extract with 100 mL of dichloromethane three times. Using TLC detection, the developer (PE: EA = 4: 1) confirmed that the reaction was complete. Use a silica gel column for purification, eluent (PE: EA = 2: 1). The product was distilled under reduced pressure to remove the solvent, and finally the product 2-pyridine propargyl ether 7c (320 mg, yield 79%) was obtained.

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Abstract

The invention discloses 2-(1',2',3'-triazolyl-4'-oxymethylenepyridyl)-1,3,4,6-O-acetyl-D-glucose with anti-rectal cancer activity. The 2-(1',2',3'-triazolyl-4'-oxymethylenepyridyl)-1,3,4,6-O-acetyl-D-glucose has a core structure of 1,3,4,6-O-acetyl-D-glucose subjected to 1,2,4-triazole derivative 2-site substitution. The above compound has good rectal cancer cell inhibition activity and can be used as a drug for resisting rectal cancer. A compound synthesis method comprises that 2-amino-D-glucose hydrochloride and an azidation reagent as raw materials undergo a reaction under alkaline conditions to produce a 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate, 3-propargyl bromide and aromatic methanol undergo a reaction under the action of sodium hydride to produce aromatic propargyl ether, and the 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate and the aromatic propargyl ether undergo a click reaction in a solvent in the presence of monovalent copper as a catalyst to produce 2-(1', 2', 3'-triazolyl-4'-oxymethylenepyridyl)-1,3,4,6-O-acetyl-D-glucose.

Description

technical field [0001] The present invention relates to the compound 2-(1',2',3'-triazole-4'-oxymethylenepyridine)-1,3,4,6-O-acetyl-D- Glucose and its preparation and application. [0002] The present invention provides a compound 2-(1',2',3'-triazole-4'-oxymethylenepyridine)-1,3,4,6-O-acetyl- D-glucose8. [0003] Background technique [0004] Rectal cancer refers to cancer between the dentate line and the rectosigmoid junction, and is one of the most common malignant tumors of the digestive tract. Rectal cancer is low in location and is easily diagnosed by digital rectal examination and sigmoidoscopy. At present, the treatment of rectal cancer needs to be based on surgery, supplemented by comprehensive treatment of chemotherapy and radiotherapy. For surgical treatment, because of its location deep into the pelvic cavity, the anatomical relationship is complicated, the operation is not easy to complete, and the postoperative recurrence rate is high. The middle and lo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/056C07H1/00A61P35/00
CPCC07H1/00C07H19/056
Inventor 付伯桥覃彩芹吕珑李伟
Owner HUBEI ENG UNIV
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