13924-94-2

Basic information

• Product Name: 5-Aminopyrazine-2-carboxylic acid methyl ester
• Synonyms: 5-Aminopyrazine-2-carboxylic acid methyl ester;5-amino-pyrazine-2-carbox...;Methyl 5-Aminopyrazine-2-carboxylate;5-aMino-pyrazine-2-carboxylic acid Methyl ester hydrochloride;5-aMinopyrazine-2-carboxylic acid Methyl ester HCl;5-AMino-2-pyrazinecarboxylic Acid Methyl Ester;Methyl 2-amino-5-pyrazinecarboxylate
• CAS NO: 13924-94-2
• Molecular Formula: C₆H₇N₃O₂
• Molecular Weight: 153.14
• Product Categories: Aromatics;Heterocycles;Miscellaneous Reagents
• Mol File: 13924-94-2.mol

Chemical Properties

• Melting Point: 230-232?C
• Boiling Point: 363℃
• Flash Point: 173℃
• Appearance: /
• Density: 1.319
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: 5-Aminopyrazine-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Aminopyrazine-2-carboxylic acid methyl ester(13924-94-2)
• EPA Substance Registry System: 5-Aminopyrazine-2-carboxylic acid methyl ester(13924-94-2)

Safety Data

• Hazardous Substances Data: 13924-94-2(Hazardous Substances Data)

Usage

Chemical Properties

Light Tan to Orange Solid

InChI:InChI=1/C6H7N3O2/c1-11-6(10)4-2-9-5(7)3-8-4/h2-3H,1H3,(H2,7,9)

Upstream product

• 169335-35-7 5-fluoro-pyrazine-2-carboxylic acid methyl ester 
• 67-56-1 methanol 
• 113305-94-5 2-amino-5-cyanopyrazine 
• 1204527-84-3 C₁₄H₁₅N₃O₃ 
• 33332-25-1 methyl 5-chloropyrazine-2-carboxylate 

Downstream Products

• 1076198-49-6 methyl 5-amino-6-bromopyrazine-2-carboxylate 
• 1380646-64-9 5-[3-(4-fluoro-phenyl)-2-(4-methanesulfonylphenyl)propionylamino]-pyrazine-2-carboxylic acid methyl ester 
• 1380645-91-9 5-[3-(4-Fluoro-phenyl)-2-(4-methanesulfonyl-phenyl)-propionylamino]-pyrazine-2-carboxylic acid ethyl ester 
• 1380645-92-0 3-(4-Fluoro-phenyl)-N-(5-hydroxymethyl-pyrazin-2-yl)-2-(4-methanesulfonyl-phenyl)-propionamide 
• 1427744-12-4 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid methyl ester 
• 1427744-25-9 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-hydroxymethyl-pyrazin-2-yl)propionamide 
• 710321-53-2 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-methanesulfonylmethyl-pyrazin-2-yl)-propionamide 

Relevant articles and documents

Design, synthesis and biological screening of 2-aminobenzamides as selective HDAC3 inhibitors with promising anticancer effects

Histone deacetylases (HDACs) have been found as a potential target for anticancer therapy. A number of HDAC inhibitors have been used pre-clinically and clinically as anticancer agents. In the current study, we have designed and synthesized compound 12a by combining the scaffolds of CI-994 and BG45. Moreover, the structure of compound 12a was optimized and a series of 2-aminobenzamide derivatives were synthesized further. These compounds were tested for their HDAC inhibitory activity and found to be efficient HDAC inhibitors. Compound 26c showed 11.68-fold HDAC3 selectivity over pan HDACs, better than the prototype HDAC3 inhibitor BG45. Most of these compounds exhibited antiproliferative activity in both B16F10 and HeLa cell lines. Particularly, compound 26c exhibited better antitumor efficacy in the cell lines compared to the prototype inhibitors CI-994 and BG45. It was also found to promote apoptosis as well as induced significant cell growth arrest in the G2/M phase of cell cycle in B16F10 melanoma cells. This work may provide significant insight regarding structural information to design newer small molecule HDAC3 inhibitors to fight against the target specific malignancies in future.

Highly efficient one-pot amination of carboxylate-substituted nitrogen-containing heteroaryl chlorides via Staudinger reaction

An efficient one-pot method for the synthesis of tert-butyl 6-aminonicotinate (5) is described. The key transformation involves displacement of the chloro group in tert-butyl 6-chloronicotinate (2) with azide followed by a Staudinger reaction. The scope of this methodology is further extended for the synthesis of a series of carboxylate-substituted heteroaryl amines. In particular, we synthesized tert-butyl carboxylate-substituted amino-pyridine, -pyridazine, and -pyrazine. In addition to one-pot conversion, short reaction time, simplicity of operation, ease of purification, and good yields are the key advantages of this methodology.

Identification of RO4597014, a glucokinase activator studied in the clinic for the treatment of type 2 diabetes

To resolve the metabolite redox cycling associated with our earlier clinical compound 2, we carried out lead optimization of lead molecule 1. Compound 4 showed improved lipophilic ligand efficiency and demonstrated robust glucose lowering in diet-induced obese mice without a liability in predictive preclinical drug safety studies. Thus, it was selected as a clinical candidate and further studied in type 2 diabetic patients. Clinical data suggests no evidence of metabolite cycling, which is consistent with the preclinical profiling of metabolism.

FUSED HETEROCYCLYC INHIBITOR COMPOUNDS

The present invention provides a compound of general Formula (I) having histone deacetylase (HDAC) and/or Cyclin-dependent kinase (CDK) inhibitory activity, a pharmaceutical composition comprising the compound, and a method useful to treat diseases using the compound

5,6-BISARYL-2-PYRIDINE-CARBOXAMIDE DERIVATIVES, PREPARATION AND APPLICATION THEREOF IN THERAPEUTICS AS UROTENSIN II RECEPTOR ANTAGONISTS

The present invention relates to derivatives of 5,6-bisaryl-2-pyridine-carboxamide, their preparation and their application in therapeutics as antagonists of urotensin II receptors.

5-SUBSTITUTED-PYRAZINE OR PYRIDINE GLUCOKINASE ACTIVATORS

The present invention provides a compound according to formula (I) where the substituent designations are provided in the specification. Pharmaceutical compositions comprising a compound according to formula (I) are also provided, said compounds being glucokinase activators which are useful in the treatment of type II diabetes.