25710-18-3

Basic information

• Product Name: 2,3-DICHLORO-PYRIDO[2,3-B]PYRAZINE
• Synonyms: 2,3-DICHLORO-PYRIDO[2,3-B]PYRAZINE
• CAS NO: 25710-18-3
• Molecular Formula: C₇H₃Cl₂N₃
• Molecular Weight: 200.02482
• Mol File: 25710-18-3.mol

Chemical Properties

• Melting Point: 144-146 °C
• Boiling Point: 282.342°C at 760 mmHg
• Flash Point: 151.584°C
• Appearance: /
• Density: 1.573g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.682
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.19±0.30(Predicted)
• CAS DataBase Reference: 2,3-DICHLORO-PYRIDO[2,3-B]PYRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DICHLORO-PYRIDO[2,3-B]PYRAZINE(25710-18-3)
• EPA Substance Registry System: 2,3-DICHLORO-PYRIDO[2,3-B]PYRAZINE(25710-18-3)

Safety Data

• Hazardous Substances Data: 25710-18-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dichloro-pyrido[2,3-b]pyrazine is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical industry, 2,3-Dichloro-pyrido[2,3-b]pyrazine serves as a key intermediate in the production of pesticides and other agrochemicals, enhancing crop protection and yield.
Used in Organic Synthesis:
2,3-Dichloro-pyrido[2,3-b]pyrazine is utilized as a building block in organic synthesis, enabling the creation of more complex compounds for various applications, including advanced materials and specialty chemicals.

InChI:InChI=1/C7H3Cl2N3/c8-5-6(9)12-7-4(11-5)2-1-3-10-7/h1-3H

Upstream product

• 2067-84-7 pyrido[3,2-b]pyrazine-2,3-diol 
• 452-58-4 2,3-Diaminopyridine 
• 144-62-7 oxalic acid 
• 2067-84-7 NSC 91561 

Downstream Products

• 1338227-54-5 2-chloro-3-(phenylethynyl)pyrido[3,2-b]pyrazine 
• 1558712-29-0 3-(4-(3-chlorobenzyl)piperazin-1-yl)-N-phenylpyrido[2,3-b]pyrazin-2-amine 

Relevant articles and documents

Discovery of a Novel Highly Selective Histamine H4 Receptor Antagonist for the Treatment of Atopic Dermatitis

The histamine H4 receptor (H4R), a member of the G-protein coupled receptor family, has been considered as a potential therapeutic target for treating atopic dermatitis (AD). A large number of H4R antagonists have been disclosed, but no efficient agents controlling both pruritus and inflammation in AD have been developed yet. Here, we have discovered a novel class of orally available H4R antagonists showing strong anti-itching and anti-inflammation activity as well as excellent selectivity against off-targets. A pharmacophore-based virtual screening system constructed in-house successfully identified initial hit compound 9, and the subsequent homology model-guided optimization efficiently led us to discover pyrido[2,3-e]tetrazolo[1,5-a]pyrazine analogue 48 as a novel chemotype of a potent and highly selective H4R antagonist. Importantly, orally administered compound 48 exhibits remarkable efficacy on antipruritus and anti-inflammation with a favorable pharmacokinetic (PK) profile in several mouse models of AD. Thus, these data strongly suggest that our compound 48 is a promising clinical candidate for treatment of AD.

A series of pyrido[2,3-b[pyrazin-3(4 H)-one derivatives as aldose reductase inhibitors with antioxidant activity

A series of pyrido[2,3-b]pyrazin-3(4H)-one based derivatives were designed as inhibitors of aldose reductase (ALR2), the enzyme which plays a key role in the development of diabetes complications as well as in the oxidative stress processes associated with diabetes and other pathologies. Most of the derivatives, having a substituted C2 aromatic group and a N4 acetic acid group on the core structure, were found to be potent and selective aldose reductase inhibitors with submicromolar IC50 values, and 9c was the most active with IC50 value 0.009 μM. Particularly, a number of the designed compounds bearing phenolic hydroxyl substituted C2-styryl side chain showed excellent not only in ALR2 inhibition but also in antioxidant, and among these 11i was proved to be the top one with an antioxidant ability even comparable to that of the well-known antioxidant Trolox. Structure-activity relationship and molecular docking studies highlighted the importance of phenolic hydroxyl substituents and vinyl spacer in C2 side chain of the scaffold for the construction of efficient and multifunctional ALR2 inhibitors.

Synthesis and evaluation of F-18 labeled pyrido[3,2-B]pyrazine derivative as a potential imaging agent for non-small-cell lung cancer

Pyridopyrazine derivatives have been known as Wnt-2/β-catenin signaling pathway inhibitors. Wnt-2 overexpression may be involved in non-small-cell lung cancer (NSCLC). A novel 2-(4-[18 F]fluorobutoxy)-3-(phenylethynyl)pyrido[3,2-b]pyrazine was prepared to demonstrate the feasibility of NSCLC imaging agent by uptake of Wnt-2 protein. It was synthesized with tosylated precursor using [18F]fluoride in radiochemical yield of 44-48%. In cellular uptake evaluation, H460 and H1299, Wnt-2 expressed cancer cell lines, showed 2.5-folds higher cellular uptake than that of MCF10A as a control.

FUSED PIPERIDINES AS IP RECEPTOR AGONISTS FOR THE TREATMENT OF PAH AND RELATED DISORDERS

The present invention provides heterocyclic derivatives which activate the IP receptor. Activating the IP receptor signaling pathway is useful to treat many forms of PAH, pulmonary fibrosis and exert beneficial effects in fibrotic conditions of various organs in animal models and in patients. Pharmaceutical compositions comprising such derivatives are also encompassed.

IP RECEPTOR AGONIST HETEROCYCLIC COMPOUNDS

The present invention provides heterocyclic derivatives which activate the IP receptor. Activating the IP receptor signaling pathway is useful to treat many forms of PAH, pulmonary fibrosis and exert beneficial effects in fibrotic conditions of various organs in animal models and in patients. Pharmaceutical compositions comprising such derivatives are also encompassed.

FUSED TRICYCLIC COMPOUNDS WITH ADENOSINE A2a RECEPTOR ANTAGONIST ACTIVITY

The present invention relates to certain certain fused tricyclic heteroaryl rings compounds of the Formula (I) (also referred to herein as the "Fused Tricyclic Compounds"), wherein M, Q, U, W, X, Y, Z, R1, R2, and R3, and rings C and D are as herein described. The present invention also provides compositions comprising at least one Fused Tricyclic Compound, and use of such compounds in the treatment of central nervous system diseases or disorders such as Parkinson's disease.

A novel 3-arylethynyl-substituted pyrido[2,3,-b]pyrazine derivatives and pharmacophore model as Wnt2/β-catenin pathway inhibitors in non-small-cell lung cancer cell lines

We developed Wnt/β-catenin inhibitors by identifying 13 number of 3-arylethynyl-substituted pyrido[2,3,-b]pyrazine derivatives that were able to inhibit the Wnt/β-catenin signal pathway and cancer cell proliferation. In the optimization process, a series of 2,3,6-trisubstituted pyrido[2,3,-b] pyrazine core skeletons showed were shown to higher activity than 2,3,6-trisubstituted quinoxaline's and thus hold promise for use as potential small-molecule inhibitors of the Wnt/β-catenin signal pathway in non-small-cell lung cancer cell (NSCLC) lines. And we have studied the pharmacophore mapping for compound 954, which presented the highest activity with a fit value of 2.81. The pharmacophore mapping for the compounds including 954, pyrido[2,3,-b]pyrazine core had hydrogen-bond acceptor site and hydrophobic center roles.

Synthesis of 9-alkyl-6-amino[1,2,4]triazolo[3,4-c]-5-azaquinoxalines. Mild and effective SNAr amination of highly electron-poor heterocycles

The synthesis and characterization of five different 9-alkyl-6-amino[1,2,3]triazolo[3,4-c]-5-azaquinoxalines is described. Due to the notable electrophilic character of the C-6 position of the [1,2,4]triazolo[3,4-c]-5-azaquinoxaline tricyclic system, SNAr amination was achieved simply by reacting the corresponding 6-chloro derivative with ammonia-saturated acetonitrile (a non-nucleophilic polar solvent) in a sealed reaction vessel, using microwave-mediated or conventional heating.

PYRAZINE DERIVATIVES AND USE AS PI3K INHIBITORS

The present invention is related to pyrazine derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

Regioselective one-pot synthesis of 9-alkyl-6-chloropyrido[3,2-e][1,2,4] triazolo-[4,3-a]pyrazines. Reactivity of aliphatic and aromatic hydrazides

(Chemical Equation Presented) The one-pot synthesis of new 9-alkyl-6-chloropyrido[3,2-e]-[1,2,4]triazolo[4,3-a]pyrazines has been achieved. Hydrazides regioselectively reacted as nucleophiles with the 3-chloro substituent of 2,3-dichloropyrido[2,3-6]pyrazine. An intramolecular cyclization afforded the tricycle nonxanthine adenosine receptor antagonists.