Category: Pyrazines

Huang, Huazhang; Nishi, Kosuke; Tsai, Hsing-Ju; Hammock, Bruce D. published an article about the compound: 5-Amino-2-fluoropyridine( cas:1827-27-6,SMILESS:NC1=CN=C(C=C1)F ).Application In Synthesis of 5-Amino-2-fluoropyridine. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:1827-27-6) through the article.

Fatty acid amide hydrolase (FAAH) is a pharmaceutical target whose inhibition may lead to valuable therapeutics. Sensitive substrates for high-throughput assays are crucial for the rapid-screening FAAH inhibitors. Here we describe the development of novel and highly sensitive fluorescent assays for FAAH based on substituted aminopyridines. Examining the relationship between the structure and the fluorescence of substituted aminopyridines suggested that a methoxy group in the para position relative to the amino group in aminopyridines greatly increased the fluorescence (i.e., quantum yields approach unity). These novel fluorescent reporters had a high Stokes’ shift of 94 nm, and their fluorescence in buffer systems increased with pH values from neutral to basic. Fluorescent substrates with these reporters displayed a very low fluorescent background and high aqueous solubility Most importantly, fluorescent assays for FAAH based on these substrates were at least 25 times more sensitive than assays using related compounds with published colorimetric or fluorescent reporters. This property results in shorter assay times and decreased protein concentrations in the assays. Such sensitive assays will facilitate distinguishing the relative potency of powerful inhibitors of FAAH. When these fluorescent substrates were applied to human liver microsomes, results suggested that there was at least one amide hydrolase in addition to FAAH that could hydrolyze long-chain fatty acid amides. These results show that these fluorescent substrates are very valuable tools in FAAH activity assays including screening inhibitors by high-throughput assays instead of using the costly and labor-intensive radioactive ligands. Potential applications of novel fluorescent reporters are discussed.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 591-54-8, is researched, SMILESS is C1=CN=CN=C1N, Molecular C4H5N3Preprint, ChemRxiv called Racemization-free synthesis of dipeptide, amide and ester by oxalyl chloride and catalytic triphenylphosphine oxide, Author is Ren, Ji-Wei; Tong, Meng-Nan; Zhao, Yu-Fen; Ni, Feng, the main research direction is dipeptide amide ester synthesis racemization steric hindrance functional group; peptide coupling amidation esterification triphenylphosphine oxide catalyst; amidation esterification reaction mechanism NMR.Application of 591-54-8.

An efficient triphenylphosphine oxide (Ph3PO) catalyzed amidation and esterification reaction for rapid synthesis of a series of dipeptides, amides and esters under mild condition is described. This reaction is applicable to challenging couplings of hindered carboxylic acid with low nucleophilic amine or alc., giving products in good yields (67-90%) without any racemization. This system employs highly reactive intermediate Ph3PCl2 as activator of carboxylate, in a catalytic manner, and drive the reaction to complete in short reaction time (less than 10 min). It has the advantages of good functional group tolerance, broad substrate scope and good atom-economy. A 100 mmol scale reaction with good yield shed light on its potential for industrial application. A plausible mechanism is proposed based on 31P NMR monitor of reaction process.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 2150-55-2, is researched, Molecular C4H6N2O2S, about Plasma persistence of 2-aminothiazoline-4-carboxylic acid in rat system determined by liquid chromatography tandem mass spectrometry, the main research direction is aminothiazoline carboxylate determination HPLC tandemMS blood forensic diagnostic biomarker.Application In Synthesis of 2-Amino-4,5-dihydrothiazole-4-carboxylic acid.

2-Aminothiazoline-4-carboxylic acid (ATCA) was i.v. injected to rats to investigate its blood plasma distribution. ATCA was extracted from plasma samples by solid phase extraction (SPE) and molecularly imprinted polymer stir bar sorption extraction (MIP-SBSE). Detection and quantification of ATCA were achieved by liquid chromatog.-tandem mass spectrometry (LC-MS/MS). It was found that the i.v. injected ATCA concentration quickly decreased to half within 2.5 h in the rat system. However, after 2.5 h, the concentration of ATCA in plasma stayed constant at least 5 folds above the endogenous ATCA level for more then 48 h. This finding can be used for evaluating ATCA’s diagnostic and forensic value as a biomarker for cyanide exposure.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 1827-27-6, is researched, Molecular C5H5FN2, about Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary Amines, the main research direction is copper catalyzed electrochem carbon hydrogen amination arene secondary amine.Electric Literature of C5H5FN2.

Electrochem. oxidation represents an environmentally friendly solution to conventional methods that require caustic stoichiometric chem. oxidants. However, C-H functionalizations merging transition-metal catalysis and electrochem. techniques are, to date, largely confined to the use of precious metals and divided cells. Herein, the authors report the 1st examples of Cu-catalyzed electrochem. C-H aminations of arenes at room temperature using undivided electrochem. cells, thereby providing a practical solution for the construction of arylamines. The use of Bu4NI as a redox mediator is crucial for this transformation. From mechanistic studies including kinetic profiles, isotope effects, cyclic voltammetric analyses, and radical inhibition experiments, the reaction appears to proceed via a single-electron-transfer (SET) process, and a high valent Cu(III) species is likely involved. These findings provide a new avenue for transition-metal-catalyzed electrochem. C-H functionalization reactions using redox mediators.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Yuan, Xinrui; Wu, Hanshu; Bu, Hong; Zheng, Peiyuan; Zhou, Jinpei; Zhang, Huibin published the article 《Design, synthesis and biological evaluation of pyridone-aminal derivatives as MNK1/2 inhibitors》. Keywords: pyridone aminal derivative preparation MNK1 MNK2 inhibitor colon cancer; MNK1/2; Pyridone–aminal; eFT508; eIF4E.They researched the compound: 4-Aminopyrimidine( cas:591-54-8 ).Product Details of 591-54-8. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:591-54-8) here.

Excessive phosphorylation of eukaryotic translation initiation factor 4E (eIF4E) plays a major role in the dysregulation of mRNA translation and the activation of tumor cell signaling. eIF4E is exclusively phosphorylated by mitogen-activated protein kinase interacting kinases 1 and 2 (MNK1/2) on Ser209. So, MNK1/2 inhibitors could decrease the level of p-eIF4E and regulate tumor-associated signaling pathways. A series of pyridone-aminal derivatives were synthesized and evaluated as MNK1/2 inhibitors. Several compounds exhibited great inhibitory activity against MNK1/2 and selected compounds showed moderate to excellent anti-proliferative potency against hematol. cancer cell lines. In particular, compound 42i (MNK1 IC50 = 7.0 nM; MNK2 IC50 = 6.1 nM) proved to be the most potent compound against TMD-8 cell line with IC50 value of 0.91 μM. Furthermore, 42i could block the phosphorylation level of eIF4E in CT-26 cell line, and 42i inhibited the tumor growth of CT-26 allograft model significantly. These results indicated that compound 42i was a promising MNK1/2 inhibitor for the potent treatment of colon cancer.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Yu, Yangsheng; Liu, Zhong; Liu, Chunqin; Li, Yang; Jin, Yongjie; Yang, Wenbo; Bai, Gang published the article 《Cloning, expression, and identification of genes involved in the conversion of DL-2-amino-Δ2-thiazoline-4-carboxylic acid to L-cysteine via S-carbamyl-L-cysteine pathway in Pseudomonas sp. TS1138》. Keywords: cloning Pseudomonas sequence enzyme tsB tsC gene cysteine production; Pseudomonas S carbamyl cysteine conversion tsB tsC gene sequence.They researched the compound: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid( cas:2150-55-2 ).HPLC of Formula: 2150-55-2. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:2150-55-2) here.

Two novel genes (tsB, tsC) involved in the conversion of DL-2-amino-Δ2-thiazoline-4-carboxylic acid (DL-ATC) to L-cysteine through S-carbamyl-L-cysteine (L-SCC) pathway were cloned from the genomic DNA library of Pseudomonas sp. TS1138. The recombinant proteins of these two genes were expressed in Escherichia coli BL21, and their enzymic activity assays were performed in vitro. It was found that the tsB gene encoded an L-ATC hydrolase, which catalyzed the conversion of L-ATC to L-SCC, while the tsC gene encoded an L-SCC amidohydrolase, which showed the catalytic ability to convert L-SCC to L-cysteine. These results suggest that tsB and tsC play important roles in the L-SCC pathway and L-cysteine biosynthesis in Pseudomonas sp. TS1138, and that they have potential applications in the industrial production of L-cysteine.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Chitneni, Satish K.; Reitman, Zachary J.; Spicehandler, Rebecca; Gooden, David M.; Yan, Hai; Zalutsky, Michael R. published an article about the compound: 5-Amino-2-fluoropyridine( cas:1827-27-6,SMILESS:NC1=CN=C(C=C1)F ).Product Details of 1827-27-6. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:1827-27-6) through the article.

Mutations in the metabolic enzyme isocitrate dehydrogenase 1 (IDH1) are commonly found in gliomas. AGI-5198, a potent and selective inhibitor of the mutant IDH1 enzyme, was radiolabeled with radioiodine and fluorine-18. These radiotracers were evaluated as potential probes for imaging mutant IDH1 expression in tumors with positron emission tomog. (PET). Radioiodination of AGI-5198 was achieved using a tin precursor in 79±6% yield (n=9), and 18F-labeling was accomplished by the Ugi reaction in a decay-corrected radiochem. yield of 2.6±1.6% (n=5). The inhibitory potency of the analogous nonradioactive compounds against mutant IDH1 (IDH1-R132H) was determined in enzymic assays. Cell uptake studies using radiolabeled AGI-5198 analogs revealed somewhat higher uptake in IDH1-mutated cells than that in wild-type IDH1 cells. The radiolabeled compounds displayed favorable tissue distribution characteristics in vivo, and good initial uptake in IDH1-mutated tumor xenografts; however, tumor uptake decreased with time. Radioiodinated AGI-5198 exhibited higher tumor-to-background ratios compared with 18F-labeled AGI-5198; unfortunately, similar results were observed in wild-type IDH1 tumor xenografts as well, indicating lack of selectivity for mutant IDH1 for this tracer. These results suggest that AGI-5198 analogs are not a promising platform for radiotracer development. Nonetheless, insights gained from this study may help in design and optimization of novel chem. scaffolds for developing radiotracers for imaging the mutant IDH1 enzyme.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 591-54-8. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Nuclear Spin Hyperpolarization of NH2- and CH3-Substituted Pyridine and Pyrimidine Moieties by SABRE. Author is Mandal, Ratnamala; Pham, Pierce; Hilty, Christian.

Hyperpolarization of N-heterocycles with signal amplification by reversible exchange (SABRE) induces NMR sensitivity gains for biol. mols. Substitutions with functional groups, in particular in the ortho-position of the heterocycle, however, result in low polarization using a typical Ir catalyst with a bis-mesityl N-heterocyclic carbene ligand for SABRE, presumably due to steric hindrance. With the addition of allylamine or acetonitrile as coligands to the precatalyst chloro(1,5-cyclooctadiene)[4,5-dimethyl-1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] iridium, the 1H signal enhancement increased in several substrates with ortho NH2 substitutions. For example, for a proton in 2,4-diaminopyrimidine, the enhancement factors increased from -7±1 to -210±20 with allylamine or to -160±10 with acetonitrile. CH3 substituted mols. yielded maximum signal enhancements of -25±7 with acetonitrile addition, which is considerably less than the corresponding NH2 substituted mols., despite exhibiting similar steric size. With the more electron-donating NH2 substitution resulting in greater enhancement, it is concluded that steric hindrance is not the only dominant factor in determining the polarizability of the CH3 substituted compounds The addition of allylamine increased the signal enhancement for the 290 Da trimethoprim, a mol. with a 2,4-diaminopyrimidine moiety serving as an antibacterial agent, to -70.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 91912-53-7, is researched, Molecular C8H8N4, about Pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6-ones. II. Synthesis and in vitro antimicrobial evaluation, the main research direction is pyrazolopyridopyrimidinone preparation bactericide fungicide; pyridopyrimidinone pyrazolo preparation bactericide fungicide; pyrimidinone pyrazolopyrido preparation bactericide fungicide.Application In Synthesis of 3-(Pyridin-4-yl)-1H-pyrazol-5-amine.

A series of pyrazolo[1,5-a]pyrido[3,4-e]pyrimidin-6-ones, I (R1 = H, Me, Ph, 2-furyl, etc., R2 = cyano, CO2Et, H, Ph, NO2, Cl, R3, R4 = H, Me), was prepared by a simple synthetic procedure based on the reaction of hydroxylamine or methoxyamine with 2,3-substituted Et 7-dimethylaminovinyl pyrazolo[1,5-a]pyrimidin-6-carboxylates II. The antimicrobial activity of the obtained compounds was evaluated on a series of standard strains of Gram pos., Gram neg. bacteria and fungi. None of the tested compounds showed significant activity.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

HPLC of Formula: 591-54-8. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Nanoscale, automated, high throughput synthesis and screening for the accelerated discovery of protein modifiers. Author is Gao, Kai; Shaabani, Shabnam; Xu, Ruixue; Zarganes-Tzitzikas, Tryfon; Gao, Li; Ahmadianmoghaddam, Maryam; Groves, Matthew R.; Doemling, Alexander.

Hit finding in early drug discovery is often based on high throughput screening (HTS) of existing and historical compound libraries, which can limit chem. diversity, is time-consuming, very costly, and environmentally not sustainable. On-the-fly compound synthesis and in situ screening in a highly miniaturized and automated format has the potential to greatly reduce the medicinal chem. environmental footprint. Here, acoustic dispensing technol. has been used to synthesize a library in a 1536 well format based on the Groebke-Blackburn-Bienayme’ reaction (GBB-3CR) on a nanomole scale. The unpurified library was screened by differential scanning fluorimetry (DSF) and cross-validated using microscale thermophoresis (MST) against the oncogenic protein-protein interaction menin-MLL. Several GBB reaction products were found as μM menin binder, and the structural basis of the interactions with menin was elucidated by co-crystal structure anal. Miniaturization and automation of the organic synthesis and screening process can lead to an acceleration in the early drug discovery process, which is an alternative to classical HTS and a step towards the paradigm of continuous manufacturing

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem