Category: Pyrazines

Structure vs. reactivity in quinoxalinecarboxylic acids and esters was written by Gum, Wilson F. Jr.;Joullie, Madeleine M.. And the article was included in Journal of Organic Chemistry in 1965.Formula: C7H8N2O2 This article mentions the following:

In an attempt to establish a correlation between the calculated electron densities in an unperturbed quinoxaline nucleus and the reactivities of its derivatives, the pK_A values of 2-, 2,3-, 6-, 5-, and 2,3-dimethyl-5-quinoxalinecarboxylic acids (I, II, III, IV, V) were measured. The carbonyl frequencies of the corresponding Me and Et esters (VI-XII) were determined by ir spectroscopy and tabulated together with those of Et and Me pyra-zinecarboxylate. Good correlation seemed to exist between pK_A values of the acids I-V and the electron d. calculated by Longuet-Higgins and Coulson (CA 41, 4978b) but only poor correlation with those reported by Basur and Bhattacharya (CA 52, 864i and by Pullman (CA 41, 197b). The split carbonyl bands observed for the esters VI-XII should be ascribed to conformational isomerism rather than to Fermi resonance. Relative pK_A values of I-V were predictable from electron densities of the unsubstituted quinoxaline ring even though the carboxylate anions formed during the determination must perturb the ring densities. The effect is apparently small in relation to the perturbed electron d. caused by the ring N atoms in the unsubstituted quinoxaline nucleus. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Formula: C7H8N2O2).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) belongs to pyrazine derivatives. Pyrazines are part of several biologically active polycyclic compounds; examples are quinoxalines, phenazines; and the bio-luminescent natural products pteridines, flavins, and their derivatives. Pyrazine and a variety of alkylpyrazines are flavor and aroma compounds found in baked and roasted goods. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human Granulocytes.Formula: C7H8N2O2

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Vicarious nucleophilic substitution of hydrogen, bisannulation and competitive reactions of α-haloalkyl carbanions with bicyclic azaaromatic compounds was written by Makosza, Mieczyslaw;Golinski, Jerzy;Ostrowski, Stanislaw;Rykowski, Andrzej;Sahasrabudhe, Arvind B.. And the article was included in Chemische Berichte in 1991.HPLC of Formula: 322-46-3 This article mentions the following:

Carbanions of RR¹CHSO₂R² (I; R = Cl, R¹ = H, Me, R² = NMe₂, Ph, CMe₃, morpholino, tolyl; R = Br, R¹ = H, R² = tolyl) react with bicyclic heteroaromatic compounds (quinoxalines, naphthyridines, and 5-azaquinoxalines) according to 2 general pathways: vicarious nucleophilic substitution (VNS) of hydrogen and/or bisannulation. In some cases other competitive reactions are observed Factors governing the direction of these reactions are discussed in terms of the charge distribution in the anionic σ adducts and the reaction conditions. For example reaction of quinoxaline and quinoxaline N-oxide with I (R = Cl, R¹ = H, R² = Ph) gave bisazirinoquinoxaline II and VNS product III resp. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3HPLC of Formula: 322-46-3).

Pyrido[2,3-b]pyrazine (cas: 322-46-3) belongs to pyrazine derivatives. Pyrazine is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. Pyrazines are chemical compounds (technically called “methoxypyrazinesâ€? found in grape skin and stems that are responsible for many “greenâ€?flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.HPLC of Formula: 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Heterogeneous and homogeneous redox catalyzed reduction of some sulfilimines was written by Griggio, L.;Severin, M. G.. And the article was included in Journal of Electroanalytical Chemistry and Interfacial Electrochemistry in 1987.SDS of cas: 322-46-3 This article mentions the following:

The homogeneous and electrode 2-electron reduction of some sulfonylsulfilimines were investigated in order to obtain more quant. kinetic and thermodn. information. The 2 processes were analyzed on the basis of homogeneous redox catalysis and voltammetric results, resp. Both reactions were shown, in most cases, to be controlled by the 1st endergonic electron uptake. The kinetic data for the process were interpreted on the basis of simple theories for electron-transfer reactions, allowing intrinsic thermodn. and activation parameters of the charge-transfer steps to be estimated The results were found to be more consistent with the hypothesis of a simple outer-sphere electron transfer followed by a fast 1st-order reaction rather than with a concerted bond breaking-charge transfer step. No relevant differences were observed owing to the replacement of Et with Ph groups in the sulfilimine moiety, the substitution effect being apparent only from a thermodn. point of view. On the contrary, the introduction of a CN group in the sulfonyl moiety increased sensibly the stability of the intermediate radical anion. This caused the electrode process kinetics to be partially dependent on the radical anion decay, allowing the quant. evaluation of its lifetime. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3SDS of cas: 322-46-3).

Pyrido[2,3-b]pyrazine (cas: 322-46-3) belongs to pyrazine derivatives. Pyrazinesare six-membered aromatic heterocyclic organic compounds with two nitrogen atoms at 1,4-positions. Pyrazine is a weaker base (pKb = 13.4) than pyridine (pKb = 8.8), pyrimidine (pKb = 12.7). A number of pyrazine-based derivatives were used as dyes or fluorescent probes.SDS of cas: 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

An efficient hydration of nitriles with ruthenium-supported heterogeneous catalyst in water under moderate conditions was written by Hussain, Muhammad Asif;Choi, Eun Ju;Maqbool, Adnan;Atif, Muhammad;Zeb, Hassan;Yeo, JaeGoo;Yu, Jung-A.;Cho, Yong-Hun;Noh, Moses;Kim, Jung Won. And the article was included in Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) in 2021.Application of 89323-09-1 This article mentions the following:

A facile eco-friendly heterogeneous catalytic system has been developed for amide synthesis that further utilized in pharmaceutical and organic chem. The Ru/MnO₂ catalyst has shown outstanding and unprecedented activity for a wide range of aliphatic and benzylic nitriles in green solvent water at 60°C. The system has also exhibited a remarkable tolerance for selective hydration of heteroatom (e.g. nitrogen, oxygen and sulfur atoms) containing nitriles. Pharmaceutically important nicotinamides and pyrazinamide has been synthesized by hydration of the heteroat. nitriles with appreciable yields and selectivities. Moreover, the Ru/MnO₂ catalyst has employed water as a benign solvent, with more than 30,000 TONs and reusability five times after isolation from the reaction mixture by centrifugation and easy workup that established a path for green environmental and technol. acceptable protocol. In the experiment, the researchers used many compounds, for example, 5-Aminopyrazine-2-carboxamide (cas: 89323-09-1Application of 89323-09-1).

5-Aminopyrazine-2-carboxamide (cas: 89323-09-1) belongs to pyrazine derivatives. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging. Pyrazines are chemical compounds (technically called “methoxypyrazinesâ€? found in grape skin and stems that are responsible for many “greenâ€?flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.Application of 89323-09-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis, structures, and spectroscopic properties of 3-aryl-5-(2-pyridyl)pyrazoles and related pyrazoles was written by Schowtka, Bjoern;Mueller, Christoph;Goerls, Helmar;Westerhausen, Matthias. And the article was included in Zeitschrift fuer Anorganische und Allgemeine Chemie in 2014.Recommanded Product: 6924-68-1 This article mentions the following:

3-Aryl-5-(2-pyridinyl)pyrazoles and related compounds I (R¹ = Ph, 4-MeC₆H₄, 3,4,5-Me₃C₆H₂, etc.; R² = 2-pyridinyl, 1-isoquinolinyl, 2-quinolinyl, etc.) were easily accessible via the reaction of the appropriate 1,3-diketone with hydrazine hydrate. The central pyrazole rings show a far-reaching equalization of the bond lengths. In the crystalline state dimeric and strand-like structures are observed due to the formation of intermol. N-H···N hydrogen bridges between the pyrazole N-H functionality and a pyrazole or pyridine base. The structures mainly depend on the steric demand of the aryl groups. Planar 3-aryl-5-(2-pyridinyl)pyrazoles also show π stacking, which reduces their solubility in common organic solvents. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Recommanded Product: 6924-68-1).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) belongs to pyrazine derivatives. Pyrazine is an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, α-hydroxyketone, α-methyl ketone. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.Recommanded Product: 6924-68-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Molecular pharmacology of the amiloride analog 3-amino-6-chloro-5-[(4-chloro-benzyl)amino]-N-[[(2,4-dimethylbenzyl)-amino]iminomethyl]-pyrazinecarboxamide (CB-DMB) as a pan inhibitor of the Na⁺-Ca²⁺ exchanger isoforms NCX1, NCX2, and NCX3 in stably transfected cells was written by Secondo, Agnese;Pannaccione, Anna;Molinaro, Pasquale;Ambrosino, Paolo;Lippiello, Pellegrino;Esposito, Alba;Cantile, Maria;Khatri, Priti R.;Melisi, Daniela;Di Renzo, Gianfranco;Annunziato, Lucio. And the article was included in Journal of Pharmacology and Experimental Therapeutics in 2009.Reference of 1458-01-1 This article mentions the following:

With the help of single-cell microfluorimetry, ⁴⁵Ca²⁺ radiotracer fluxes, and patch-clamp in whole-cell configuration, the authors examined the effect of the amiloride derivative 3-amino-6-chloro-5-[(4-chloro-benzyl)amino]-N-[[(2,4-dimethylbenzyl) amino]-iminomethyl]-pyrazinecarboxamide (CB-DMB) on the activity of the three isoforms of the Na⁺/Ca²⁺ exchanger (NCX) and on several other membrane currents including voltage- and pH-sensitive ones. This amiloride analog suppressed the bidirectional activity of all NCX isoforms in a concentration-dependent manner. The IC₅₀ values of CB-DMB were in the nanomolar range for the outward and the inward components of the bidirectional NCX1, NCX2, and NCX3 activity. Deletion mutagenesis showed that CB-DMB inhibited NCX activity mainly at level of the f-loop but not through the interaction with Gly 833 located at the level of the α₂ repeat. CB-DMB suppressed in the micromolar range the other plasma membrane currents encoded by voltage-dependent Ca²⁺ channels, tetrodotoxin-sensitive Na⁺ channels, and pH-sensitive ASIC1a. Collectively, the data of the present study showed that CB-DMB, when used in the nanomolar range, is one of the most potent compounds that can block the activity of the three NCX isoforms when they work both in the forward and in the reverse modes of operation without interfering with other ionic channels. In the experiment, the researchers used many compounds, for example, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1Reference of 1458-01-1).

Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1) belongs to pyrazine derivatives. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging.Reference of 1458-01-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Degradation behavior of poly(ethylene glycol) dicarboxylic acid (2-hydroxymethyl-3,5,6-trimethylpyrazine) ester in vitro was written by Xia, Cheng-jian;Wang, Song;Zhu, He-sun. And the article was included in Jingxi Huagong in 2004.Formula: C8H12N2O This article mentions the following:

Poly(ethylene glycol) (PEG) dicarboxylic acid (2-hydroxymethyl-3,5,6-trimethylpyrazine) ester (patented by BIT) was prepared in 92% yield by condensation of PEG-10000 and 2-hydroxymethyl-3,5,6-trimethylpyrazine with 1,1′-carbonyldiimidazole (CDI) as condensating agent. The product was characterized by m.p., FTIR and ¹HNMR: m.p. 53 âˆ?55 °C; FTIR absorption 1747 cm^-1 (C=O), 1254 cm^-1 (C-O-C); ¹HNMR δ = 1.9 (-CH₃, 3H, s), 2.2 (-CH₃, 6H, s), 4.2 (-CH₂-, 2H, s), 3.6 (-OCH₂-, multi – H, s). The hydrolytic degradation of the ester in vitro was performed and results indicated that the degradation rate was pH-dependent. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Formula: C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. Pyrazines are chemical compounds (technically called “methoxypyrazinesâ€? found in grape skin and stems that are responsible for many “greenâ€?flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.Formula: C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Enhanced performance of quasi-solid-state dye-sensitized solar cells by tuning the building blocks in D-(π)-A’-π-A featured organic dyes was written by Lan, Tian;Lu, Xuefeng;Zhang, Lu;Chen, Yijing;Zhou, Gang;Wang, Zhong-Sheng. And the article was included in Journal of Materials Chemistry A: Materials for Energy and Sustainability in 2015.Product Details of 148231-12-3 This article mentions the following:

D-(π)-A’-π-A featured organic dyes with different numbers of 3,4-ethylenedioxythiophene (EDOT) bridges and different anchoring groups, i.e., cyanoacrylic acid or rhodanine-3-acetic acid, have been designed and synthesized for application in quasi-solid-state dye-sensitized solar cells (DSSCs). The absorption, electrochem. and photovoltaic properties are systematically studied. Upon the incorporation of an auxiliary EDOT unit into sensitizers FNE60 and FNE61 with D-A’-π-A configuration, sensitizers FNE62 and FNE63 with D-π-A’-π-A configuration exhibit much broader absorption spectra, which is beneficial to the light-harvesting capability and photocurrent generation. When the cyanoacrylic acid group in sensitizers FNE60 and FNE62 is replaced by a much stronger electron-withdrawing group, rhodanine-3-acetic acid, strengthened intramol. charge transfer interactions are realized, which results in the significantly bathochromically shifted maximum absorption wavelengths for sensitizers FNE61 and FNE63. However, the methylene group in the rhodanine-3-acetic acid unit interrupts the LUMO delocalization on the anchoring group in sensitizers FNE61 and FNE63, as revealed by theor. calculation, which may result in less effective electron injection from the LUMO to the conduction band of the TiO₂ semiconductor. Consequently, the quasi-solid-state DSSC based on FNE62 exhibits a highest power conversion efficiency of 8.2%, which illustrates good long-term stability after continuous light soaking for 1000 h. In the experiment, the researchers used many compounds, for example, 5,8-Dibromoquinoxaline (cas: 148231-12-3Product Details of 148231-12-3).

5,8-Dibromoquinoxaline (cas: 148231-12-3) belongs to pyrazine derivatives. Pyrazine is an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, α-hydroxyketone, α-methyl ketone. Pyrazines are chemical compounds (technically called “methoxypyrazinesâ€? found in grape skin and stems that are responsible for many “greenâ€?flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.Product Details of 148231-12-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The out-of-plane vibrations of aza-aromatic molecules was written by Chappell, P. J.;Ross, I. G.. And the article was included in Journal of Molecular Spectroscopy in 1977.SDS of cas: 322-46-3 This article mentions the following:

A transferable valence force field is developed for application to the out-of-plane vibrations of C6H6, naphthalene, and their aza analogs. Existing vibrational frequency assignments are rationalized and in some cases extensively revised. The mols. treated are quinoline and isoquinoline; 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3- and 2,7-diazanaphthalene; 1,3,5-, 1,3,6-, 1,3,7-, 1,3,8-, 1,4,5- and 1,4,6-triazanaphthalene; and 1,3,5,8-, 1,4,5,8- and 2,3,6,7-tetraazanaphthalene. The assignment of the planar frequencies at 350-1000 cm-1 is also reviewed for these mols. The calculations on the azabenzenes are discussed. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3SDS of cas: 322-46-3).

Pyrido[2,3-b]pyrazine (cas: 322-46-3) belongs to pyrazine derivatives. Pyrazine derivatives have antitumor, antibiotic, anticonvulsant, antituberculous and diuretic effects as well as kinase, enzymatic and potent tubulin and FtsZ polymerization inhibitory activities. A number of pyrazine-based derivatives were used as dyes or fluorescent probes.SDS of cas: 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

BA-12 inhibits angiogenesis via glutathione metabolism activation was written by Cui, Herong;Guo, Wenbo;Zhang, Beibei;Li, Guoping;Li, Tong;Yuan, Yanyan;Zhang, Na;Yang, Yuwei;Feng, Wuwen;Chu, Fuhao;Wang, Shenglan;Xu, Bing;Wang, Penglong;Lei, Haimin. And the article was included in International Journal of Molecular Sciences in 2019.Safety of (3,5,6-Trimethylpyrazin-2-yl)methanol This article mentions the following:

There is a need for an efficient and low-cost leading compound discovery mode. However, drug development remains slow, expensive, and risky. Here, this manuscript proposes a leading compound discovery strategy based on a combination of traditional Chinese medicine (TCM) formulas and pharmacochem., using a ligustrazine-betulinic acid derivative (BA-12) in the treatment of angiogenesis as an example. Blocking angiogenesis to inhibit the growth and metastasis of solid tumors is currently one recognized therapy for cancer in the clinic. Firstly, based on a traditional Prunella vulgaris plaster, BA-12 was synthesized according to our previous study, as it exhibited better antitumor activities than other derivatives on human bladder carcinoma cells (T24); it was then uploaded for target prediction. Secondly, the efficacy and biotoxicity of BA-12 on angiogenesis were evaluated using human umbilical vein endothelial cells (HUVECs), a quail chick chorioallantoic membrane, and Caenorhabditis elegans. According to the prediction results, the main mechanisms of BA-12 were metabolic pathways. Thus, multiple metabolomics approaches were applied to reveal the mechanisms of BA-12. Finally, the predictive mechanisms of BA-12 on glutathione metabolism and glycerophospholipid metabolism activation were validated using targeted metabolomics and pharmacol. assays. This strategy may provide a reference for highly efficient drug discovery, with the aim of sharing TCM wisdom for unmet clin. needs. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Safety of (3,5,6-Trimethylpyrazin-2-yl)methanol).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging. A large number of pyrazine derivatives are known for their antitumor, antibiotic, anticonvulsant, antituberculosis, and diuretic activities.Safety of (3,5,6-Trimethylpyrazin-2-yl)methanol

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem