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9-(diethoxy) phosphonomethyl purine, preparation method and application thereof in antineoplastic aspect

A technology of diethoxy and adenine, which is applied in antineoplastic drugs, chemical instruments and methods, and pharmaceutical formulations, can solve problems in the initial stage and achieve the effect of easy operation

Inactive Publication Date: 2010-11-24
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, some studies on nucleoside phosphate prodrug compounds have been carried out, and such prodrugs [Bis(POM)-(PMEA)] and [Bis(POM)- (PMPA)], but in general, research in this area is still in its infancy, and more research is needed to find nucleoside phosphate prodrugs with excellent activity. Currently, the nucleoside phosphate prodrugs 9-(two Ethoxy) phosphonomethyladenine content has not been reported in the literature

Method used

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  • 9-(diethoxy) phosphonomethyl purine, preparation method and application thereof in antineoplastic aspect
  • 9-(diethoxy) phosphonomethyl purine, preparation method and application thereof in antineoplastic aspect
  • 9-(diethoxy) phosphonomethyl purine, preparation method and application thereof in antineoplastic aspect

Examples

Experimental program
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Effect test

Embodiment 1

[0032] (1) Synthesis of α-iodomethyl diethyl phosphate

[0033]Add diiodomethane (81mL, 1.00mol) into a 500mL three-necked flask equipped with a condensing side tube, heat to 110°C, the color of diiodomethane begins to darken, at this time slowly add triethyl phosphite, dropwise The temperature rises rapidly during the process, indicating that the reaction has begun. When the temperature rises to 140°C, the heat source is removed quickly, and the temperature is strictly controlled so that it cannot exceed 150°C. Triethyl phosphite (180mL, 1.05mol) is added dropwise until the reaction temperature begins. decrease, indicating that the reaction is complete. After complete cooling, a light yellow liquid was obtained. Distill it under reduced pressure at 13mmHg. When the temperature is 70-90°C, two fractions are distilled out successively. Then adjust the vacuum degree and distill under reduced pressure at 8mmHg. The temperature rises to 106°C, and the third fraction is distilled ...

Embodiment 2

[0037] (1) Synthesis of α-iodomethyl diethyl phosphate

[0038] Add diiodomethane (81mL, 1.00mol) into a 500mL three-necked flask equipped with a condensing side tube, heat to 110°C, the color of diiodomethane begins to darken, at this time slowly add triethyl phosphite, dropwise The temperature rises rapidly during the process, indicating that the reaction begins. When the temperature rises to 120°C, the heat source is removed quickly, and the temperature is strictly controlled so that it cannot exceed 130°C. Triethyl phosphite (180mL, 1.05mol) is added dropwise until the reaction temperature begins. decrease, indicating that the reaction is complete. After complete cooling, a light yellow liquid was obtained. Distill it under reduced pressure at 13mmHg. When the temperature is 70-90°C, two fractions are distilled out successively. Then adjust the vacuum degree and distill under reduced pressure at 8mmHg. The temperature rises to 106°C, and the third fraction is distilled ou...

Embodiment 3

[0042] (1) Synthesis of α-iodomethyl diethyl phosphate

[0043] Add diiodomethane (81mL, 1.00mol) into a 500mL three-necked flask equipped with a condensing side tube, heat to 100°C, the color of diiodomethane begins to darken, at this time slowly add triethyl phosphite, dropwise The temperature rises rapidly during the process, indicating that the reaction begins. When the temperature rises to 120°C, the heat source is removed quickly, and the temperature is strictly controlled so that it cannot exceed 130°C. Triethyl phosphite (180mL, 1.05mol) is added dropwise until the reaction temperature begins. decrease, indicating that the reaction is complete. After complete cooling, a light yellow liquid was obtained. Distill it under reduced pressure at 13mmHg. When the temperature is 70-90°C, two fractions are distilled out successively. Then adjust the vacuum degree and distill under reduced pressure at 8mmHg. The temperature rises to 106°C, and the third fraction is distilled ou...

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Abstract

The invention discloses an acyclic nucleoside phosphate compound, i.e. 9-(diethoxy) phosphonomethyl purine, a preparation method and application thereof in the antineoplastic aspect. The structural formula of the compound is shown as the following specification. In the preparation method, the 9-(diethoxy) phosphonomethyl purine is prepared by two reactions by using methylene diiodide, triethyl-phosphite and adenine as raw materials, using N,N-dimethyl formamide, dimethyl sulfoxide, methanol and ethanol as solvents and using anhydrous potassium carbonate and sodium methoxide as catalysts. The compound has a certain inhibiting effect on the hepatoma cell BEL-7402.

Description

Technical field: [0001] The invention relates to a 9-(diethoxy) phosphonomethyl adenine compound; the invention also relates to a synthesis method of the compound and an anti-tumor application. Background technique: [0002] Tumor is a disease that seriously threatens human health. No anti-tumor drug has been found so far. However, since nitrogen mustard was used to treat malignant lymphoma in 1943, considerable progress has been made in anti-cancer chemotherapy for decades. In recent years, nucleoside drugs have received widespread attention as the main therapeutic drugs for viral diseases. Nucleoside drugs used to treat human immunodeficiency virus (HIV) and herpes simplex virus (HSV) infections are generally inhibitors of HIV reverse transcriptase and HSV deoxyribonucleic acid (DNA) polymerase. Therefore, nucleoside drugs have good therapeutic effects on many viral diseases. Although nucleosides and their analogs are widely used as anti-tumor and anti-viral drugs clinic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561A61K31/675A61P35/00
Inventor 詹天荣杨波程坤侯万国
Owner QINGDAO UNIV OF SCI & TECH