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4-Alanine substituted cytosine nucleosides and their medicinal uses

A technology of cytidine nucleoside derivatives and alanine, which is applied in the direction of drug combination, organic chemistry, and pharmaceutical formulations, and achieves the effects of low toxicity, good application prospects, and simple and feasible preparation methods

Active Publication Date: 2021-10-19
HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing literature, there is no relevant report on the application of 4-alanine-substituted cytosine nucleoside compounds in anti-Coxsackie virus (CVB) virus drugs

Method used

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  • 4-Alanine substituted cytosine nucleosides and their medicinal uses
  • 4-Alanine substituted cytosine nucleosides and their medicinal uses
  • 4-Alanine substituted cytosine nucleosides and their medicinal uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of compound BG001:

[0028] Compound 1 ((50mg, 0.12mmol) was added to methylamine aqueous solution (5mL, mass percent concentration 40%) at room temperature, and then continued to stir for 2 hours. After the reaction was detected by TLC, the solvent was distilled off under reduced pressure, and quickly Column separation (dichloromethane:methanol=5:1) gave white powdery solid compound BG001

[0029] (48 mg, 96%). 1 H NMR (400Hz, CD 3 OD):7.73-7.71(1H,dd,J=1.2,7.6 Hz),6.50-6.46(1H,dd,J=7.2,12.0Hz),5.98-5.96(1H,d,J=7.6 Hz),5.26 -5.12(1H,m),4.61-4.60(1H,m),4.50-4.44(1H,dd,J=4.4, 21.6Hz),3.83(2H,s),2.74(3H,m),1.40-1.38 (3H,m); 13 C NMR (100Hz, CD 3 OD): 175.5, 165.2, 158.2, 142.0, 98.6 (J FC =6.7Hz), 97.1, 97.1, 95.2 (J FC =189.7Hz), 84.9(J FC =17.5Hz), 76.5(J FC =24.3Hz), 63.5, 51.1, 18.3.

Embodiment 2

[0030] Embodiment 2: the synthesis of compound BG003:

[0031] Compound 1 (50mg, 0.12mmol) was added to concentrated ammonia water (10ml, mass percentage concentration 17%) at room temperature, and then continued to stir for 2 hours. After the reaction was detected by TLC, the solvent was distilled off under reduced pressure, and the column was separated quickly. (dichloromethane:methanol=3:1) to obtain white powdery solid compound BG003 (46 mg, 96%). 1 H NMR (400Hz, CD 3 OD):7.72-7.70(1H,d,J=7.6Hz),6.50-6.46(1H,dd,J=7.2,12.4Hz),5.99-5.97(1H,d,J=8.0Hz),5.27-5.11 (1H,ddd, J=4.4,9.2,58.4Hz),4.69-4.63(1H,m),4.50-4.44(1H,dd,J=4.8, 21.6Hz),3.83(2H,s),1.42-1.41 (3H,m); 13 C NMR (100Hz, CD 3 OD): 177.6, 165.2, 158.2, 141.9, 98.6 (J FC =7.6Hz), 97.1, 95.2 (J FC =188.9Hz), 84.9(J FC =16.7Hz), 76.5(J FC =25.0Hz), 63.4, 18.4.

Embodiment 3

[0032] Embodiment 3: the synthesis of compound BG004:

[0033] Compound 1 (50mg, 0.12mmol) was added to ethylamine aqueous solution (4ml, mass percent concentration 60%) at room temperature, and then continued to stir for 2 hours. After the reaction was detected by TLC, the solvent was distilled off under reduced pressure, and the column was flashed. Isolation (dichloromethane:methanol=5:1) gave white powdery solid compound BG004 (50 mg, 97%). 1 H NMR (400Hz, CD 3 OD):7.72-7.70(1H,dd,J=1.2,7.6Hz),6.50-6.46 (1H,dd,J=7.2,12.0Hz),5.98-5.96(1H,d,J=7.6Hz),5.26 -5.11(1H, ddd, J=4.4,7.2,49.2Hz),4.63-4.57(1H,m),4.50-4.44(1H,dd,J=4.4, 21.6Hz),3.83(2H,s),3.24 -3.18(2H,m),1.41-1.39(3H,m),1.13-1.09(3H,m); 13 C NMR (100Hz, CD 3 OD): 174.6, 165.1, 158.1, 142.0, 131.0, 98.5 (J FC =6.7Hz), 97.1, 95.2 (J FC =191.0Hz), 84.8(J FC =17.5Hz), 76.4(JFC =21.6Hz), 63.4,51.1,35.4,18.3.

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Abstract

The invention discloses novel 4-alanine substituted cytosine nucleoside compounds and their medicinal use, belonging to the field of medicinal chemistry. It has the structure of general formula (I): in the formula, R=NH 2 ,C 1 -C 10 Alkylamines, preferably: R=NH 2 , NHCH 3 ,NHCH 2 CH 3 . Alanine methyl ester to 4-alanine methyl ester-1-(2'-deoxy-2'-β-fluoro-4'-α-azido-β-D-furanosyl)cytosine Modified and synthesized 4-alanine substituted pyrimidine nucleoside derivatives, this type of compound has anti-Coxsackie virus activity; it has a good application prospect in the treatment of viral myocarditis.

Description

technical field [0001] The invention relates to pyrimidine nucleoside compounds, in particular to 4-alanine substituted cytosine nucleoside compounds, a synthesis method and a medicinal application thereof, and belongs to the field of medicinal chemistry. Background technique [0002] Viral myocarditis is a disease mainly caused by viral infection, which is mainly caused by myocardial inflammation, accounting for about 50% of myocarditis. Due to the different severity of the disease, the clinical manifestations of patients vary greatly, depending on the extent and location of the lesion. Mild cases may be asymptomatic, and severe cases may be complicated by severe arrhythmia, cardiac insufficiency, and dilated cardiomyopathy, or even Sudden death is a serious threat to life and health, especially to children and adolescents. In terms of the current medical level and the needs of patients, there is still an urgent need for effective drugs for the treatment of viral myocardit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04A61P9/00A61P31/12A61P31/14A61P31/20A61P31/18A61K31/506
CPCA61P9/00A61P31/12A61P31/14A61P31/18A61P31/20C07D405/04
Inventor 郭晓河陶乐李玉江常俊标董黎红王强余学军郑果
Owner HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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