168123-87-3

Basic information

• Product Name: 7-Trifluoromethyl-1,4-dihydro-pyrido[2,3-b]pyrazine-2,3-dione
• Synonyms: 7-Trifluoromethyl-1,4-dihydro-pyrido[2,3-b]pyrazine-2,3-dione
• CAS NO: 168123-87-3
• Molecular Formula: C8H4F3N3O2
• Molecular Weight: 231.1314696
• Mol File: 168123-87-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Trifluoromethyl-1,4-dihydro-pyrido[2,3-b]pyrazine-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Trifluoromethyl-1,4-dihydro-pyrido[2,3-b]pyrazine-2,3-dione(168123-87-3)
• EPA Substance Registry System: 7-Trifluoromethyl-1,4-dihydro-pyrido[2,3-b]pyrazine-2,3-dione(168123-87-3)

Safety Data

• Hazardous Substances Data: 168123-87-3(Hazardous Substances Data)

Usage

General Description

7-Trifluoromethyl-1,4-dihydro-pyrido[2,3-b]pyrazine-2,3-dione is a chemical compound that belongs to the pyrazine and pyridine classes of compounds. It is a heterocyclic compound with a molecular formula C8H5F3N2O2 and a molecular weight of 220.13 g/mol. This chemical is used in the pharmaceutical industry as a building block for the synthesis of various drugs and biologically active compounds. It has potential applications in the development of new pharmaceutical products due to its unique structure and properties. Furthermore, research on this compound's potential biological activities and pharmacological properties is ongoing, with the goal of discovering new therapeutic agents for various diseases.

Upstream product

• 79-37-8 oxalyl dichloride 
• 107867-51-6 5-(trifluoromethyl)-2,3-pyridinediamine 
• 95-92-1 oxalic acid diethyl ester 
• 74784-70-6 2-amino-5-trifluoromethylpyridine 
• 53359-69-6 5-(Trifluoromethyl)-3-nitro-2-aminopyridine 

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.

5-(N-oxyaza)-7-substituted-1,4-dihydroquinoxaline-2,3-diones: Novel, systemically active and broad spectrum antagonists for NMDA/glycine, AMPA, and kainate receptors

A group of 5-aza-7-substituted-1,4-dihydroquinoxaline-2,3-diones (QXs) and the corresponding 5-(N. oxyaza)-7-substituted QXs were prepared and evaluated as antagonists of ionotropic glutamate receptors. The in vitro potency of these QXs was determined by inhibition of [3H]-5,7- dichlorokynurenic acid ([3H]DCKA) binding to N-methyl-D-aspartate (NMDA)/glycine receptors, [3H]-(S)-α-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid ([3H]AMPA) binding to AMPA receptors, and [3H]kainate ([3H]KA) binding to KA receptors in rat brain membranes. 5-(N- Oxyaza)-QXs 12a-e all have low micromolar or submicromolar potency for NMDA/glycine receptors and low micromolar potencies for AMPA and KA receptors. QXs 12a-e display 2-12-fold selectivity for NMDA/glycine receptors compared to AMPA receptors, and ~2-fold difference between AMPA and KA potency. In contrast to other QXs that either show high selectivity for NMDA (such as ACEA 1021) or AMPA (such as NBQX) receptors, these molecules are broad spectrum antagonists of ionotropic glutamate receptors. 7-Nitro-5-(N- axyaza)-QX (12e) is the most potent inhibitor among 12a-e, having IC50 values of 0.69, 1.3, and 2.4 μM at NMDA, AMPA, and KA receptors, respectively. In functional assays on glutamate receptors expressed in oocytes by rat cerebral cortex poly(A+) RNA, 7-chloro-5-(N-oxyaza)-QX (12a) and 7-nitro-5(N-oxyaza)-QX (12e) have K(b) values of 0.63 and 0.31 μM for NMDA/glycine receptors, and are 6- and 4-fold selective for NMDA over AMPA receptors, respectively. 5-(N-Oxyaza)-7-substituted-QXs 12a-e all have surprisingly high in vivo potency as anticonvulsants in a mouse maximal electroshock-induced seizure (MES) model. 7-Chloro-5-(N-oxyaza)-QX (12a), 7- bromo-5-(N-oxyaza)-QX (12b), and 7-methyl-5-(N-oxyaza)-QX (12c) have ED50 values of 0.82, 0.87, and 0.97 mg/kg iv, respectively. The high in vivo potency of QXs 12a-e is particularly surprising given their low log P values (~ -2.7). Separate studies indicate that QXs 12a and 12e are also active in vive as neuroprotectants and also have antinociceptive activity in animal pain models. In terms of in vivo activity, these 5-(N-oxyaza)-7-substituted- QXs are among the most potent broad spectrum ionotropic glutamate antagonists reported.

Synthesis and biological evaluation of pyrido[2,3-b]pyrazine and pyrido[2,3-b]pyrazine-N-oxide as selective glycine antagonists

Pyrido[2,3-b]pyrazines and pyrido[2,3-b]pyrazines-N-oxides have been synthesized and evaluated for in vitro/in vivo antagonistic activity at the glycine site on the NMDA receptor.