Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Nucleic acid, peptide nucleicacid derivatives and their use

A technology of peptide nucleic acid and nucleoside analogs, which is applied in the field of nucleic acid and peptide nucleic acid derivatives, and can solve problems such as failure to reach

Inactive Publication Date: 2006-08-09
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
View PDF0 Cites 13 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, simulating its function with simple small molecules is too simplistic and hardly achieves the intended purpose.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Nucleic acid, peptide nucleicacid derivatives and their use
  • Nucleic acid, peptide nucleicacid derivatives and their use
  • Nucleic acid, peptide nucleicacid derivatives and their use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] 1.1 1-(2-deoxy-3,5-di-oxo-p-methylbenzoyl-β-D-erythro-ribose)-5-(2-hydroxyethyl)-1H,3H-pyrimidine-2 , 4-diketone (1)

[0108] Suspend 5-hydroxyethyluracil (4g, 25.64mmol) in hexamethyldisilazane (20ml), add a small amount of ammonium sulfate, heat the mixture, and reflux overnight. After the remaining hexamethyldisilazane was distilled off under reduced pressure, chloroform (400ml) was added, followed by 1-chloro-2-deoxy-3,5-di-p-methylbenzoyl ribose (12g, 30.89mmol) and cuprous iodide (5.9 g, 30.89 mmol), stirred at room temperature for 3 hours. The mixture was poured into a saturated sodium bicarbonate solution, stirred for 1 h, the organic layer was separated, washed once with water, dried with anhydrous sodium sulfate, filtered and concentrated to obtain a syrupy liquid, which was separated by column chromatography as a colorless solid product. 11.5 g, yield 88.5%. R f (CH 2 Cl 2 / CH 3 OH 20:1) 0.35. 1 H NMR (d6-DMSO): 2.26(t, J=6.7Hz, 5-CH 2 CH 2 O), 2.39...

Embodiment 2

[0119] 2.15-(3-tert-butyldiphenylsiloxypropyl)-uracil (6)

[0120] According to the method of Example 1.3, in dichloromethane (20ml), with 5-(3-trihydroxypropyl)uracil (1.5g, 8.81mmol), imidazole (0.66g, 9.7mmol), tert-butyldiphenyl Chlorosilane (2.56ml, 9.8mmol) gave the product 3-tert-butyldiphenylsiloxypropyluracil, 3.4g, yield 94.4%. R f (CH 2 Cl 2 / CH 3 OH 20:1) 0.15. Elemental Analysis: C 23 h 28 N 2 o 3 Si (M 408.57), theoretical: C 67.61, H 6.91, N 6.86; found: C 67.56, H 6.78, N 6.74. 1 H NMR (d6-DMSO): 0.99 (s, tBu), 1.69 (m, 5-CH 2 CH 2 CH 2 ), 2.25(t, J=7.3Hz, 5-CH 2 CH 2 CH 2 ), 3.62(t, J=6.3Hz, 5-CH 2 CH 2 CH 2 ), 7.15 (s, 6-H), 7.45, 7.61 (2m, Ph), 11.01, 10.63 (s, 2NH).

[0121] 2.2 1-(2-Deoxy-3,5-di-oxo-p-methylbenzoyl-β-D-erythro-ribose)-5-(2-diphenyltert-butylsiloxypropyl)- 1H,3H-pyrimidine-2,4-dione (7)

[0122] According to the method of Example 1.1, after 5-(3-tert-butyldiphenylsiloxypropyluracil (2.4g, 5.88mmol) was silanized with he...

Embodiment 3

[0131] 3.1 1-(β-D-erythro-2-deoxy-ribose)-1H,3H-pyrimidine-2,4-dione-5-propionic acid methyl ester (12)

[0132] It was prepared according to the synthesis method of compound 1. After obtaining compound 11, the deprotection reaction was carried out directly to obtain compound 12, 2.6 g, with a yield of 45.6%. R f (CH 2 Cl 2 / CH 3 OH 9:1) 0.42. Elemental Analysis: C 13 h 18 N 2 o 7 (M 314.29), Theoretical: C 49.68, H 5.77, N 8.91; Found: C 49.67, H 5.52, N 8.47. 1 H NMR (d6-DMSO): 2.08 (m, 2'-H), 2.48 (m, 5-CH 2 CH 2 ), 3.59 (s, CH 3 ), 3.56(m, 5'-H), 3.77(m, 4'H), 4.24(m, 3'-H), 5.03(t, J=5.2Hz, 5'-OH), 5.24(d, J = 4.2 Hz, 3'-OH), 6.16 (t, J = 6.9 Hz, 1'-H), 7.72 (s, 6-H), 11.33 (s, NH).

[0133] 3.2 1-(β-D-erythro-deoxy-ribose)-1H,3H-pyrimidine-2,4-dione 5-propionamide (13)

[0134] Ammonia / methanol solution (70 ml) of compound 12 (0.5 g, 1.59 mmol) was placed in a closed container and stirred at room temperature for 7 days. The reaction solution was concentrat...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to nucleic acid and peptide nucleic acid derivative, their preparation method, product, and use in medicine and biology field.

Description

field of invention [0001] The present invention relates to nucleic acid and peptide nucleic acid derivatives, their preparation methods, products containing them, and their uses in the fields of medicine and biology. Background technique [0002] Using synthetic compounds to simulate the structure and function of biomacromolecules, especially biomacromolecules with specific functions, has important scientific significance for further understanding and elucidating their functions and mechanisms in vivo. These include macromolecule-macromolecule, macromolecule-small molecule interactions, and even interactions between molecular complexes. Such as the interaction between enzymes and substrates, the interaction between antibodies and antigens, the interaction between receptors and drugs (including chemical drugs and biological drugs), and so on. Based on the research results of the molecular mechanism of action, it is of great significance to use specific functions to develop i...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07H19/02C07H19/06C07K2/00C12Q1/68A61K31/7068A61K31/7084A61K38/02
Inventor 刘克良何军林梁远军魏霞褚征张迪徐亮
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com