41270-70-6

Usage

Class

Pyrazine derivatives

Structure

Heterocyclic aromatic compound with a five-membered ring, two nitrogen atoms, three carbon atoms

Functional groups

Two phenyl groups, one amino group

Applications

Organic synthesis, pharmaceutical industries

Uses

Intermediate in chemical compound and pharmaceutical drug production

Potential

Biological activities, pharmacological properties

Upstream product

• 532-54-7 E-isonitrosoacetophenone 
• 53641-60-4 2-phenylglycinonitrile hydrochloride 
• 26764-39-6 dichlorobis(benzonitrile)palladium(II) 
• 7688-25-7 1,4-di(diphenylphosphino)-butane 
• 98-80-6 phenylboronic acid 
• 960-16-7 tributylphenylstannane 
• 344940-70-1 5-bromo-3-phenyl-pyrazin-2-amine 
• 41270-63-7 2-chloro-3,5-diphenylpyrazine 
• 60-35-5 acetamide 
• 76849-28-0 2-azido-3,5-diphenylpyrazine 
• 24241-18-7 2-amino-3,5-dibromopyrazine 

Downstream Products

• 74152-22-0 2-acetamino-3,5-diphenylpyrazine 

Relevant academic research and scientific papers

2-Aminoaryl-3,5-diaryl pyrazines: Synthesis, biological evaluation against Mycobacterium tuberculosis and docking studies

Rationally designed Mycobacterium tuberculosis (Mtb) inhibitors were synthesized under Buchwald conditions using Pd2(dba)3/xantphos and the compounds were investigated for their biological activity against the Mtb standard strain H37Rv and two other clinically isolated multidrug-resistant strains with different drug resistance patterns. Compounds 5e, 6e, 7e, and 8e exhibited excellent antituberculosis activity against H37Rv with a minimum inhibitory concentration (MIC) value of 15 μg/ml. Compounds 5a, 6c, 7b, 8a, 8b, and 8d also displayed their potency with a MIC value in the range of 15–25 μg/ml. In addition to the Mtb studies, compounds 4e, 5e, 7e, and 8e were tested for cytotoxicity on HEK-293 cells and compounds 7e and 8e were identified to have low toxicities of up to 200 and 300 μM, respectively. The synthesized compounds docked with the 2FUM protein of Mtb and the docking studies revealed that compounds 5e, 6e, 7e, and 8e can bind strongly in the active site of the enzyme and showed binding energies of ?9.62, ?10.7, ?11.48, and ?12.06 kcal/mol, respectively. Compound 7e forms four hydrogen bonds, whereas compound 8e forms five hydrogen bonds with amino acids, respectively. Based on these results, compounds 7e and 8e might be considered potential lead compounds with good anti-Mtb potency.

Design, Synthesis, and Biological Evaluation of 3,5-Disubstituted 2-Pyrazineamide Derivatives as Antitubercular Agents

A novel series of 3,5-disubstituted-2-pyrazineamide derivatives (5a–5o) were synthesized and studied for their potential as antitubercular agents. Among them, the compounds 5a, 5g, and 5m showed the good minimal inhibitory concentration of 20, 25, and 25?μg/mL, respectively. The compound 5a displayed excellent minimum inhibitory concentration of 10?μg/mL and is four times more potent compared with the standard drug, rifampicin concentration. In silico docking studies revealed that the compounds 5a and 5c can bind strongly in the active site of 2FUM enzyme and prevent enzyme–substrate interactions. In addition, in silico docking studies were calculated, and based on the data obtained, compound 5a displayed excellent drug-like properties.

Compound and application thereof

The compound has the structure shown in the formula (1), X is CH or N, and L is selected from a single bond. The substituted or unsubstituted C6 - C60 arylene group, the substituted or unsubstituted C3 - C60 heteroarylene group, the Ar is selected from one of a substituted or unsubstituted C6 - C60 aryl group, a substituted or unsubstituted C3 - C60 heteroaryl group. When the compound provided by the invention is applied OLED devices, the efficiency of the device can be effectively improved, the driving voltage is reduced, and the compound is a good-performance electronic transmission material.

RED-SHIFTED LUCIFERASE-LUCIFERIN PAIRS FOR ENHANCED BIOLUMINESCENCE

A bioluminescent protein is provided that includes a substituted luciferase polypeptide having amino acid substitutions at positions 21 and 166, and with one or more additional amino acid substitutions at positions 3, 16, 20, 29, 30, 71, 87, 114, and 144, compared to the parent polypeptide. Also provided is a luciferin that has a selenium-containing group at position C8 of an imidazopyrazine backbone, and methods of making the luciferin. In addition, nucleic acids encoding the bioluminescent protein, cells expressing the bioluminescent protein, and reactions between the bioluminescent protein and luciferin substrates are also provided. Fusions between the substituted luciferase polypeptide and a fluorescent protein are also provided for bioluminescence resonance energy transfer based reporters.

Synthesis and chemiluminescent properties of 6,8-diaryl-2-methylimidazo[1, 2-a]pyrazin-3(7H)-ones: Systematic investigation of substituent effect at para-position of phenyl group at 8-position

6,8-Diphenylimidazopyrazinone derivatives having a substituent R (R = CF3, H, and OMe) at para position of the 8-phenyl group were synthesized and their chemiluminescent properties were investigated. The chemiluminescence maxima (CLmax/su

Well-divided and pH-dependent bimodal chemiluminescence of 2-methyl-6-phenyl-8-(4-substituted phenyl)-imidazo[1,2-a]pyrazin-3(7h)-ones induced by superoxide anion

An unprecedented pH-dependent bimodal chemiluminescence of 2-methyl-6-phenyl-8-(4-substituted phenyl)imidazo[1,2-a]pyrazin-3(7H)-ones (1a and 1b) initiated by superoxide anion (O2.-) in phosphate buffer solutions is described. The intensity rat

Synthesis of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones and their chemiluminescent properties

A series of 3,7-dihydroimidazo[1,2a]pyrazine-3-ones were prepared from 2-amino-3,5-dibromopyrazine. The concise synthesis of coelenterazine (5j), in three steps, 48% overall yield and >99% purity exemplifies the strategy. Further, the synthetic approach facilitated the regiospecific incorporation of carboxyalkyl linkers on the 3,7-dihydroimidazo[1,2a]pyrazine-3-one nucleus that are required for bioconjugation. Peroxymonocarbonate, an electrophilic oxidant, was used to initiate 'pseudo-flash' chemiluminescence from this class of molecules.

Efficient synthesis of substituted 2-aminopyrazines: FeCl3-promoted condensation of hydroxyiminoketones with aminoacetonitriles

FeCl3-promoted condensation of hydroxyiminoketones with aminoacetonitriles followed by catalytic hydrogenation afforded the desired pyrazines in moderate-good yields. This protocol provides an efficient and practical synthesis of substituted 2-

Chemi- and bioluminescence of coelenterazine analogues with a conjugated group at the C-8 position

The chemiliminescent compound coelenterazine is involved in various bioluminescence reactions as the substrates, causing the luminescence with an emission peak in the range of 450-475 nm. Anticipating the introduction of a bathochromicshift of the lumines

Studies on pyrazines; part 30: Synthesis of aminopyrazines from azidopyrazines

Azidopyrazines do not undergo reduction by reagents that are effective for the preparation of alkyl- or arylamines from the azides because the heterocyclic azides exist in the bicyclic form of tetrazolo[1,5-a]pyrazines. Nevertheless, the conversion into aminopyrazines was achieved by hydrogenolysis in the presence of ammonium hydroxide and palladium-on-carbon or particularly by reduction with tin(II) chloride in methanolic hydrochloric acid, in 34-87% yields. To elucidate the successful progress of the reaction, the equilibrium of azide-atetrazole was examined by 1H NMR spectroscopy in various solvents.