Synthetic method of 5-amino-4-carbamyl imidazole ribavirin carbocyclic analog

A technology of carbamoyl imidazole riboside carbon and synthesis method, which is applied in the field of synthesis of 5-amino-4-carbamyl imidazole riboside carbocyclic analogs, can solve the problem of harsh synthesis method conditions, high synthesis reaction cost and environmental problems. Serious pollution and other problems, to achieve the effect of good environmental protection, fewer reaction steps, and high reaction quality

Active Publication Date: 2017-01-18
PHARMA SHANGHAI
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] , this synthetic method has harsh conditions, high synthetic reaction cost, low yield, and serious environmental pollution

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
  • Synthetic method of 5-amino-4-carbamyl imidazole ribavirin carbocyclic analog

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0018] The following will clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only some of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by persons of ordinary skill in the art without making creative efforts belong to the protection scope of the present invention.

[0019] see figure 1 , provide a kind of synthetic method of 5-amino-4-carbamoyl imidazolidine carbocyclic analogue, comprising the steps of:

[0020] (1) 0.24 g, 1.1 mmol of (3aR,4S,6R,6aS)-methyl-6-amino-2,2-dimethyltetrahydro-3ahydro-cyclopenta[d][1,3] Dioxy-4-carboxylate was dissolved in 5 mL of acetonitrile, and 0.19 g, 1.3 mmol of triethyl orthoformate and 0.13 g, 1.3 mmol of 2-amino-2-cyanoacetamide were added in sequence. The reaction solution was heated to reflux in acetonitrile for 12 hours, cooled, added ...

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 discloses a synthesis method of 5-formamidoimidazole-4-carboxamide ribotide analogue. The analysis method comprises the following steps: by taking (3aR,4S,6R,6aS)-methyl-6-amino-2,2-dimethyltetrahydro-3ahydro-cyclo[d][1,3]dioxo-4-carboxylate, triethyl orthoformate and 2-amino-2-cyanoacetamide as raw materials, conducting loop closing through reflux reaction to obtain an intermediate, reducing with lithium borohydride, reacting with phosphorus oxychloride, and then hydrolyzing to obtain the 5-formamidoimidazole-4-carboxamide ribotide analogue. In the mode, the synthesis method of the 5-formamidoimidazole-4-carboxamide ribotide analogue comprises few reaction steps, is mild in reaction conditions, convenient in refining, simple to carry out, high in reaction quality, high in yield, and good in environment friendliness.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for synthesizing 5-amino-4-carbamoyl imidazole ribavirin carbocyclic analogues. Background technique [0002] At present, 5-amino-4-imidazolecarbox-amide-riboside (5-amino-4-imidazolecarbox-amide-riboside, AICAR) and its carbocyclic analogue (C-AICAR) have been widely used in research as AMPK activators . Adenylate-activated protein kinase (AMPK) belongs to serine / threoninase protein kinase, widely exists in eukaryotic cells, is the sensor of cellular energy regulation, and is responsible for energy regulation and delivery. AMPK is not active under physiological conditions. When cells are in a state of stress and energy exhaustion, the ratio of AMP / ATP will increase, and AMPK can be activated by upstream genes to restore the ratio of AMP / ATP to normal. Research data in recent years have shown that AMPK activation of tumor cells can produce cytotoxicity, so drugs that...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6506
Inventor 林友刚
Owner PHARMA SHANGHAI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap