Category: Pyrazines

Singh, Baljinder; Diaz-Gonzalez, Rosario; Ceballos-Perez, Gloria; Rojas-Barros, Domingo I.; Gunaganti, Naresh; Gillingwater, Kirsten; Martinez-Martinez, Maria Santos; Manzano, Pilar; Navarro, Miguel; Pollastri, Michael P. published an article about the compound: 4-Aminopyrimidine( cas:591-54-8,SMILESS:C1=CN=CN=C1N ).Formula: C4H5N3. 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:591-54-8) through the article.

Human African trypanosomiasis (HAT), or sleeping sickness, is caused by the protozoan parasite Trypanosoma brucei and transmitted through the bite of infected tsetse flies. The disease is considered fatal if left untreated. To identify new chemotypes against Trypanosoma brucei, previously we identified 797 potent kinase-targeting inhibitors grouped into 59 clusters plus 53 singleton compounds with at least 100-fold selectivity over HepG2 cells. From this set of hits, a cluster of diaminopurine-derived compounds was identified. Herein, we report our medicinal chem. investigation involving the exploration of structure-activity and structure-property relationships around one of the high-throughput screening (HTS) hits, N2-(thiophen-3-yl)-N6-(2,2,2-trifluoroethyl)-9H-purine-2,6-diamine (1, NEU-1106). This work led to the identification of a potent lead compound (4aa, NEU-4854) with improved in vitro absorption, distribution, metabolism, and excretion (ADME) properties, which was progressed into proof-of-concept translation of in vitro antiparasitic activity to in vivo efficacy.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

COA of Formula: C4H5N3. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Discovery, synthesis and optimization of an N-alkoxy indolylacetamide against HIV-1 carrying NNRTI-resistant mutations from the Isatis indigotica root. Author is Xu, Chengbo; Xin, Yijing; Chen, Minghua; Ba, Mingyu; Guo, Qinglan; Zhu, Chenggen; Guo, Ying; Shi, Jiangong.

From an aqueous decoction of the traditional Chinese medicine “”ban lan gen”” (the Isatis indigotica root), an antiviral natural product I [R1 = Me; R2 = 2-CO2Me; n = 1] was isolated as an NNRTI (non-nucleoside reverse transcriptase inhibitor) (EC50 = 3.40μM). Its novel structure was determined as Me (1-methoxy-1H-indol-3-yl)acetamidobenzoate I [R1 = Me; R2 = 2-CO2Me; n = 1] by spectroscopic data and confirmed by single crystal X-ray diffraction. Through synthesis and structure-activity relationship (SAR) investigation of compound I [R1 = Me; R2 = 2-CO2Me; n = 1] and 57 new derivatives I [R1 = Me, n-Pr, Bn, etc.; R2 = Ph, 2-ClC6H4, 2-pyridyl, etc.; n = 1,2,3] (24 with EC50 values of 0.06-8.55μM), two optimized derivatives I [R1 = n-Pr, n-Bu; R2 = 3-chloro-4-pyridyl; n = 1] (EC50: 0.06μM and 0.06μM) having activity comparable to that of NVP (EC50 = 0.03μM) were obtained. Further evaluation verified that compounds I [R1 = n-Pr, n-Bu; R2 = 3-chloro-4-pyridyl; n = 1] were RT DNA polymerase inhibitors and exhibited better activities and drug resistance folds compared to NVP against seven NNRTI-resistant strains carrying different mutations. Especially, compound I [R1 = n-Bu; R2 = 3-chloro-4-pyridyl; n = 1] (EC50 = 0.43μM) was more active to the L100I/K103N double-mutant strain as compared to both NVP (EC50 = 0.76μM) and EFV (EC50 = 1.08μM). The mol. docking demonstrated a possible binding pattern between compound I [R1 = n-Bu; R2 = 3-chloro-4-pyridyl; n = 1] and RT and revealed activity mechanism of compound I [R1 = n-Bu; R2 = 3-chloro-4-pyridyl; n = 1] against the NNRTI-resistant strains.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Shipin Kexue (Beijing, China) called Effect of dissolved oxygen on production of L-cysteine synthetase by Pseudomonas sp. TS1138, Author is Huai, Lihua; Chen, Ning, which mentions a compound: 2150-55-2, SMILESS is O=C(C1N=C(N)SC1)O, Molecular C4H6N2O2S, Name: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid.

Pseudomonas sp. TS1138 has potential to produce L-cysteine synthetase through asym. hydrolysis of DL-2-amino-Δ2-thiazoline-4-carboxylic acid (DL-ATC). The effect of dissolved oxygen level on the production of L-cysteine synthetase was investigated in shake flasks or 7 L bioreactor. The results indicated that the cell growth and the production of L-cysteine synthetase were inhibited at low dissolved oxygen level. Although cell growth was improved at the high dissolved oxygen level, the inhibition against production of L-cysteine synthetase was still observed in shake flasks. In 7 L bioreactor, dissolved oxygen concentration controlled at more than 30% was helpful for improving the cell growth and the production of L-cysteine synthetase through regulating agitation rate and air flow rate during the middle and late stage.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about Synthesis of 2-guanidinyl pyridines and their trypsin inhibition and docking, the main research direction is guanidinylpyridine synthesis trypsin inhibition docking; safety allergic reaction aminomethoxymethylnicotinamide; Enzymology; Halogen bonding; Hydrogen bonding; Inhibitor; Molecular docking; Pyridin-2-yl guanidine; Serine protease.Name: 4-Aminopyrimidine.

A range of guanidine-based pyridines, and related compounds, have been prepared (19 examples). These compounds were evaluated in relation to their competitive inhibition of bovine pancreatic trypsin. Results demonstrate that compounds in which the guanidinyl substituent can form an intramol. hydrogen bond (IMHB) with the pyridinyl nitrogen atom are better trypsin inhibitors than their counterparts that are unable to form an IMHB. Among the compounds 6a-p, examples containing a 5-halo substituent were, generally, found to be better trypsin inhibitors. This trend was inversely related to electronegativity, thus, 1-(5-iodopyridin-2-yl)guanidinium ion 6e (I.TFA) (Ki = 0.0151 mM) was the optimum inhibitor in the 5-halo series. Amongst the isomeric Me substituted compounds, 1-(3-methylpyridin-2-yl)guanidinium ion 6h (II.TFA) demonstrated optimum levels of trypsin inhibition (Ki = 0.0140 mM). In order to rationalize the measured enzyme inhibition, selected compounds were docked with bovine and human trypsin with a view to understanding active site occupancy and taken together with the Ki values the order of inhibitory ability suggests that the 5-halo 2-guanidinyl pyridine inhibitors form a halogen bond with the catalytically active serine hydroxy group. Safety: severe allergic reactions have been reported with 6-amino-N-methoxy-N-methylnicotinamide.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Name: 3-(Pyridin-4-yl)-1H-pyrazol-5-amine. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 3-(Pyridin-4-yl)-1H-pyrazol-5-amine, is researched, Molecular C8H8N4, CAS is 91912-53-7, about Synthesis and study of the anti-inflammatory properties of some pyrazolo[1,5-a]pyrimidine derivatives. Author is Bruni, Fabrizio; Costanzo, Annarella; Selleri, Silvia; Guerrini, Gabriella; Fantozzi, Roberto; Pirisino, Renato; Brunelleschi, Sandra.

A series of pyrazolo[1,5-a]pyrimidin-7-ones I (R = bromophenyl, methoxyphenyl, thienyl, pyridyl, cyclohexyl, Bu, iso-Pr, nitrophenyl, aminophenyl hydrochloride, and ethylpyridinium iodide) were synthesized to evaluate in vivo and in vitro effects induced by structural modifications at the 2 position of 4,7-dihydro-4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one (FPP028). This substance, which has been previously studied, is a weak inhibitor of prostaglandin biosynthesis and a nonacid analgesic and anti-inflammatory agent devoid of ulcerogenic properties. To gain more insight into the mechanism of action of this class of compounds, several in vivo tests were carried out, such as carrageenan-induced rat paw edema and pleurisy. In vitro tests include some studies of leukocyte functions, such as superoxide production and myeloperoxidase release. In vitro effects on arachidonic acid-, ADP, and platelet-activating factor-induced platelet aggregation were also studied. Different anti-inflammatory activities were observed, depending on the nature of substituents at the 2 position; these differences are probably linked to the capacity of these compounds to inhibit leukotrienes and/or prostaglandin biosynthesis with different selectivity. 4,7-Dihydro-4-ethyl-2(2-thienyl)pyrazolo[1,5-a]pyrimidin-7-one proved to be the most interesting compound of the novel synthesized series, showing powerful pharmacol. activity in vivo as well as in vitro, together with very weak acute toxicity.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of C4H6N2O2S. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid, is researched, Molecular C4H6N2O2S, CAS is 2150-55-2, about Simultaneous analysis of 28 urinary VOC metabolites using ultra high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry (UPLC-ESI/MSMS). Author is Alwis, K. Udeni; Blount, Benjamin C.; Britt, April S.; Patel, Dhrusti; Ashley, David L..

Volatile organic compounds (VOCs) are ubiquitous in the environment, originating from many different natural and anthropogenic sources, including tobacco smoke. Long-term exposure to certain VOCs may increase the risk for cancer, birth defects, and neurocognitive impairment. Therefore, VOC exposure is an area of significant public health concern. Urinary VOC metabolites are useful biomarkers for assessing VOC exposure because of non-invasiveness of sampling and longer physiol. half-lives of urinary metabolites compared with VOCs in blood and breath. We developed a method using reversed-phase ultra high performance liquid chromatog. (UPLC) coupled with electrospray ionization tandem mass spectrometry (ESI/MSMS) to simultaneously quantify 28 urinary VOC metabolites as biomarkers of exposure. We describe a method that monitors metabolites of acrolein, acrylamide, acrylonitrile, benzene, 1-bromopropane, 1,3-butadiene, carbon-disulfide, crotonaldehyde, cyanide, N,N-dimethylformamide, ethylbenzene, ethylene oxide, propylene oxide, styrene, tetrachloroethylene, toluene, trichloroethylene, vinyl chloride and xylene. The method is accurate (mean accuracy for spiked matrix ranged from 84 to104%), sensitive (limit of detection ranged from 0.5 to 20 ng mL-1) and precise (the relative standard deviations ranged from 2.5 to 11%). We applied this method to urine samples collected from 1203 non-smokers and 347 smokers and demonstrated that smokers have significantly elevated levels of tobacco-related biomarkers compared to non-smokers. We found significant (p < 0.0001) correlations between serum cotinine and most of the tobacco-related biomarkers measured. These findings confirm that this method can effectively quantify urinary VOC metabolites in a population exposed to volatile organics There are many compounds similar to this compound(2150-55-2)Synthetic Route of C4H6N2O2S. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Recommanded Product: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid, is researched, Molecular C4H6N2O2S, CAS is 2150-55-2, about Comparison of cyanide exposure markers in the biofluids of smokers and non-smokers. Author is Vinnakota, Chakravarthy V.; Peetha, Naga S.; Perrizo, Mitch G.; Ferris, David G.; Oda, Robert P.; Rockwood, Gary A.; Logue, Brian A..

Cyanide is highly toxic and is present in many foods, combustion products (e.g. cigarette smoke), industrial processes, and has been used as a terrorist weapon. In this study, cyanide and its major metabolites, thiocyanate and 2-amino-2-thiazoline-4-carboxylic acid (ATCA), were analyzed from various human biofluids of smokers (low-level chronic cyanide exposure group) and non-smokers to gain insight into the relationship of these biomarkers to cyanide exposure. The concentrations of each biomarker tested were elevated for smokers in each biofluid. Significant differences (p < 0.05) were found for thiocyanate in plasma and urine, and ATCA showed significant differences in plasma and saliva. Addnl., biomarker concentration ratios, correlations between markers of cyanide exposure, and other statistical methods were performed to better understand the relationship between cyanide and its metabolites. Of the markers studied, the results indicate plasma ATCA, in particular, showed excellent promise as a biomarker for chronic low-level cyanide exposure. In addition to the literature in the link below, there is a lot of literature about this compound(2-Amino-4,5-dihydrothiazole-4-carboxylic acid)Recommanded Product: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid, illustrating the importance and wide applicability of this compound(2150-55-2).

Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Product Details of 2150-55-2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid, is researched, Molecular C4H6N2O2S, CAS is 2150-55-2, about Continuous L-cysteine production using immobilized cell reactors and product extractors. Author is Ryu, Ok Hee; Ju, Jae Yeong; Shin, Chul Soo.

Methods to improve the stability of L-cysteine-producing enzymes from Pseudomonas sp. M-38, both as whole cells and as immobilized cells, were investigated for the production of L-cysteine from DL-2-amino-Δ2-thiazoline-4-carboxylic acid (DL-ATC). Among the 3 L-cysteine-producing enzymes, only L-ATC hydrolase was unstable. However, the stability of L-ATC hydrolase was significantly enhanced by the addition of 20% sorbitol. In continuous L-cysteine production, >60% of the initial activity of L-ATC hydrolase remained after 1000 h at 37° with 40% sorbitol and at 30° with 20% sorbitol. A system involving a cascade of processes using 2 packed-bed reactors with immobilized cells and 2 L-cysteine extractors with the ion-exchange resin Dowex 50W was developed to reduce product inhibition and unreacted substrate. The overall productivity of the system was 43% higher than for 2 reactors without an ion-exchange extractor.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Molecules called Energetic and Geometric Characteristics of the Substituents: Part 2: The Case of NO2, Cl, and NH2 Groups in Their Mono-Substituted Derivatives of Simple Nitrogen Heterocycles, Author is Wieczorkiewicz, Pawel A.; Szatylowicz, Halina; Krygowski, Tadeusz M., which mentions a compound: 591-54-8, SMILESS is C1=CN=CN=C1N, Molecular C4H5N3, Safety of 4-Aminopyrimidine.

Variously substituted N-heterocyclic compounds are widespread across bio- and medicinal chem. The work aims to computationally evaluate the influence of the type of N-heterocyclic compound and the substitution position on the properties of three model substituents: NO2, Cl, and NH2. For this reason, the energetic descriptor of global substituent effect (Erel), geometry of substituents, and electronic descriptors (cSAR, pEDA, sEDA) are considered, and interdependences between these characteristics are discussed. Furthermore, the existence of an endocyclic N atom may induce proximity effects specific for a given substituent. Therefore, various quantum chem. methods are used to assess them: the quantum theory of atoms in mols. (QTAIM), anal. of non-covalent interactions using reduced d. gradient (RDG) function, and electrostatic potential maps (ESP). The study shows that the energetic effect associated with the substitution is highly dependent on the number and position of N atoms in the heterocyclic ring. Moreover, this effect due to interaction with more than one endo N atom (e.g., in pyrimidines) can be assessed with reasonable accuracy by adding the effects calculated for interactions with one endo N atom in substituted pyridines. Finally, all possible cases of proximity interactions for the NO2, Cl, and NH2 groups are thoroughly discussed.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of C5H5FN2. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 5-Amino-2-fluoropyridine, is researched, Molecular C5H5FN2, CAS is 1827-27-6, about Synthesis of 6-substituted pyrido[3,4-d]pyrimidin-4(3H)-ones via directed lithiation of 2-substituted 5-aminopyridine derivatives.

Directed lithiation of Boc or pivaloyl derivatives of 2-substituted 5-aminopyridines I (R = Cl, F, OMe, R1 = COnCMe3, X = H, n = 1, 2) with BuLi-TMEDA in di-Et ether at -10°C gave 4-lithio derivatives which were quenched with CO2 to give the analogous C-4 carboxylic acids I (X = CO2H). Hydrolysis of the protecting groups with either TFA or aqueous KOH gave 2-substituted 5-aminopyridine-4-carboxylic acids I (R1 = H, X = CO2H) which were converted to 6-substituted pyrido[3,4-d]pyrimidin-4(3H)-ones II by reaction with formamide or, more optionally, formamidine acetate. Boc protected aminopyridines provided the best overall results, with synthesis of these derivatives best achieved by direct reaction of the aminopyridine with di-tert-Bu dicarbonate in the absence of added base.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem