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4-amino-acid-substituted pyrimidine nucleoside compound and medicinal application thereof

A technology of pyrimidine nucleoside derivatives and amino acids, which is applied in the field of pyrimidine nucleoside compounds and 4-amino acid substituted pyrimidine nucleoside compounds, and can solve problems such as 4-amino acid substituted pyrimidine nucleoside compounds that have not yet been discovered

Active Publication Date: 2019-01-25
HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing literature, no relevant reports have been found on the application of 4-amino acid substituted pyrimidine nucleoside compounds in anti-CVB virus drugs

Method used

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  • 4-amino-acid-substituted pyrimidine nucleoside compound and medicinal application thereof
  • 4-amino-acid-substituted pyrimidine nucleoside compound and medicinal application thereof
  • 4-amino-acid-substituted pyrimidine nucleoside compound and medicinal application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Take compound GY005 (0.44g, 1mmol), add methanol (20ml) to dissolve at room temperature, add water (20ml) and potassium carbonate (1.38g, 10mmol), and stir overnight at room temperature, the raw materials are completely reacted on the plate, and dilute hydrochloric acid (1N, 25mL), the solvent was distilled off under reduced pressure, separated by column chromatography (dichloromethane:methanol:acetic acid=90:10:1) to obtain compound GY001 (100mg, 24%) and compound GY002 (260mg, 60%), GY001: HRMS (M+Na):453.1130; 1 H-NMR (DMSO-d6, 400Hz), δ: 8.52 (brs, 1H, NH), 7.61 (d, 1H, J=8.0Hz, CH), 6.36-6.46 (m, 2H, CH 2 ), 5.93 (d, 1H, J=7.2Hz, CH), 5.74 (brs, 1H, OH), 5.10-5.24 (m, 1H, CH), 4.42-4.55 (m, 2H, CH 2 ), 3.72(s, 2H), 3.65(s, 3H, OCH 3 ), 2.28-2.33 (m, 2H, CH 2 ), 1.82-2.06 (m, 2H, CH 2 ).

[0034] GY002: HRMS (M+Na) 453.1123; 1 H-NMR (DMSO-d6, 400Hz), δ: 7.8 (brs, 1H, NH), 7.51 (d, 1H, J=8.0Hz, CH), 6.36-6.43 (m, 2H, CH 2 ), 6.0 (d, 1H, J=8.0Hz, CH), 5.71 (brs...

Embodiment 2

[0036] Take compound GY005 (0.44g, 1mmol), add methanol (20mL) to dissolve at room temperature, add sodium hydroxide solution (1M, 5mL), react at room temperature overnight, add acetic acid (0.5mL), column chromatography (dichloromethane: methanol : acetic acid=80:18:2), to obtain GY003 (415 mg, 98%) as a white powdery solid. HRMS(M+Na)439.0970: 1 H-NMR (CD 3 OD, 400Hz), δ: 7.71(d, 1H, J=8.0Hz, CH), 6.46-6.50(dd, 1H, J=4.8, 7.2Hz, CH), 6.1(d, 1H, J=8.0Hz, CH), 5.11-5.27 (ddd, 1H, J=4.0, 4.2, 44.4Hz, CH), 4.83 (brs, 1H, CH), 4.44-4.51 (dd, 1H, J=4.4, 17.2Hz, CH), 3.84 (s, 2H, CH 2 ), 2.43 (brs, 2H, CH 2 ), 2.01-2.26 (m, 2H, CH 2 ).

Embodiment 3

[0038]Take compound GY005 (0.21g, 0.5mmol), add methanol (20mL) to dissolve at room temperature, then add solid potassium hydroxide (65mg, 1.2mmol), stir at room temperature for 2h, concentrate to dryness, wash with cold ethanol twice, and dry in vacuo GY004 was obtained as a white powdery solid (0.23 g, 92%). HRMS(M+H)415.7743; 1 H-NMR (D 2 O, 400Hz), δ: 7.87 (d, 1H, J = 8.4Hz, CH), 7.64 (d, 1H, J = 7.2Hz, CH), 6.50-6.54 (dd, 1H, J = 5.2, 5.6Hz, CH), 6.08(d, 1H, J=8.0Hz, CH), 5.19-5.35(ddd, 1H, J=5.2, 4.8, 43.6Hz, CH), 4.48-4.54(m, 1H, CH), 3.93- 3.94 (m, 2H, CH 2 ), 2.27-2.31 (m, 2H, CH 2 ), 1.94-2.15 (m, 2H, CH 2 ).

[0039] The above are only part of the embodiments of the present invention, and are not intended to limit the present invention in any form. Any simple modifications made to the above embodiments according to the technical essence of the present invention, equivalent changes and modifications, all belong to this invention. within the scope of the techni...

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Abstract

The invention discloses a 4-amino-acid-substituted pyrimidine nucleoside compound and a synthesis method and medicinal application thereof and belongs to the field of medicinal chemistry. The compoundhas a structure shown as a formula (I) which is described in the description, wherein in the formula (I), R1 refers to H, CH3, CH2CH3, K and Na, R2 refers to H, CH3, CH2CH3, K and Na, and when R1 andR2 do not represent CH3 at the same time, L-glutamic acid dimethyl ester in 4-(L-glutamic acid dimethyl ester)-1-(2'-deoxidized-2'-beta-fluoro-4'-alpha-nitrine-beta-D-furan glycosyl)cytosine is modified, so that a series of 4-amino-acid-substituted pyrimidine nucleoside derivatives are synthesized, and these compounds have the activity of resisting Coxsackie virus 3. A preparation method is feasible, and the 4-amino-acid-substituted pyrimidine nucleoside compound is applied to drugs for treating viral myocarditis and has a great application prospect.

Description

technical field [0001] The invention relates to pyrimidine nucleoside compounds, in particular to 4-amino acid substituted pyrimidine nucleoside compounds, a synthesis method and a medicinal application thereof, belonging to the field of medicinal chemistry. Background technique [0002] Viral myocarditis is a disease mainly caused by viral infection, mainly caused by myocardial inflammation. In recent years, the incidence has been on the rise in my country and has become a common disease that endangers human health. So far, there is no very effective treatment. Developing new antiviral drugs, or designing new therapeutic drugs for its pathogenesis is an important way to study viral myocarditis drugs (Journal of South China University. Medical Edition, 2002, 30(1): 1-6). [0003] Coxsackie virus B (CVB) is one of the important human pathogens, it can cause epidemic chest pain, aseptic meningitis, meningoencephalitis and pericarditis, especially it can cause human myocarditi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/06C07H1/00A61P9/00A61P31/14
CPCA61P9/00A61P31/14C07H1/00C07H19/06
Inventor 郭晓河陶乐李玉江董黎红刘陆平王强余学军
Owner HIGH & NEW TECH RES CENT OF HENAN ACAD OF SCI
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