Category: Pyrazines

Synthesis, spectral characterization, dna interaction and anticancer evaluation of transition metal complexes of hydroxamic acid derivative was written by Hegde, Divya S.;Gudasi, Kalagouda B.. And the article was included in World Journal of Pharmacy and Pharmaceutical Sciences in 2016.Safety of Ethyl pyrazine-2-carboxylate This article mentions the following:

A novel tetradentate chelating ligand, N閳?(1-(hydroxyamino)-1-oxopropan-2-ylidene)pyrazine-2-carbohydrazide and its Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) complexes were synthesized and characterized by elemental analyses, spectral (vibrational, electronic, ¹H NMR,¹³C NMR and Mass) and thermal studies. The interaction of ligand and complexes with calf-thymus DNA (CT-DNA) has been extensively studied using absorption, emission, viscosity and thermal denaturation studies with E. coli DNA. The DNA cleavage ability of ligand and metal complexes was tested using plasmid pBR322 DNA by gel electrophoresis method. The compounds were evaluated for their in vitro antiproliferative activity against human cancer cells of different origin such as MCF-7, Mia-Pa-Ca-2 and DU-145 by using SRB(sulforhodamineB) assay. The copper and iron complex have shown better anticancer activity as compared to other compounds under study. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Safety of Ethyl pyrazine-2-carboxylate).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) 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). Pyrazine-based skeletons were incorporated into agents targeting a range of ailments. Many derivatives were synthesized and evaluated as potential cancer treatments.Safety of Ethyl pyrazine-2-carboxylate

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Development of Large-Scale Routes to Potent GPR119 Receptor Agonists was written by Matsuoka, Richard T.;Boros, Eric E.;Brown, Andrew D.;Bullock, Kae M.;Canoy, Will L.;Carpenter, Andrew J.;Cobb, Jeremy D.;Condon, Shannon E.;Deschamps, Nicole M.;Elitzin, Vassil I.;Erickson, Greg;Fang, Jing M.;Igo, David H.;Joshi, Biren K.;Kaldor, Istvan W.;Mitchell, Mark B.;Peckham, Gregory E.;Reynolds, Daniel W.;Salmon, Matthew C.;Sharp, Matthew J.;Tabet, Elie A.;Toczko, Jennifer F.;Wu, Lianming Michael;Zhou, Xiao-ming M.. And the article was included in Organic Process Research & Development in 2016.Recommanded Product: 2-Bromo-5-chloropyrazine This article mentions the following:

Practical and scalable syntheses were developed that were used to prepare multi kilogram batches of GSK1292263A (1) and GSK2041706A (15), two potent G protein-coupled receptor 119 (GPR119) agonists. Both syntheses employed relatively cheap and readily available starting materials, and both took advantage of an S_NAr synthetic strategy. In the experiment, the researchers used many compounds, for example, 2-Bromo-5-chloropyrazine (cas: 912773-21-8Recommanded Product: 2-Bromo-5-chloropyrazine).

2-Bromo-5-chloropyrazine (cas: 912773-21-8) 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. 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.Recommanded Product: 2-Bromo-5-chloropyrazine

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis, mechanochromism and acid response of fluorescence dyes based on quinoxalines modified with tetraphenylethlenes was written by Sun, Jingbo;Zhang, Gonghe;Jia, Xiaoyu;Xue, Pengchong;Jia, Junhui;Lu, Ran. And the article was included in Huaxue Xuebao in 2016.Recommanded Product: 148231-12-3 This article mentions the following:

Three new D-锜?A type quinoxalines modified with tetraphenylethylenes BTPQ, DBTPQ and BTBQ were synthesized via Suzuki coupling reactions between (4-(1,2,2-triphenylvinyl)phenyl)boronic acid and bromo aromatic hydrocarbons. It was found that BTPQ and DBTPQ, in which tetraphenylethylenes were substituted on 5,8-positions of quinoxalines gave the absortion bands at 316 nm and 303 nm, resp., originated from 锜?锜? transition. For BTBQ, in which tetraphenylethylene units were located at 2,3-positions of quinoxaline, the 锜?锜? transition absorption blue-shifted to 287 nm on account of the poor planarity and low conjugation. Meanwhile, the intermol. charge transfer (ICT) emission could be detected for BTPQ and DBTPQ, whose emission bands red-shifted significantly and emission intensities decreased with increasing the solvent polarities. It should be noted that the three compounds exhibited aggregation-induced emission (AIE) behaviors. For instance, when the water faction in the THF solution increased to 90%, the emission intensity at ca. 400 nm for BTBQ, was ca. 54 times higher than that in THF. Addnl., trifluoroacetic acid (TFA) could lead to the changes of color and emitting color of BTBQ in solution as well as in solid state due to the formation of protonated quinoxaline. We found that the gray solid of BTBQ could turn into red one upon exposed to gaseous TFA, accompanying with the quench of the emission. Other kinds of acids of HCl, HNO₃ and acetic acid also could lead to the fluorescence quenching of solid BTBQ to some extent. Therefore, BTBQ could be used as sensory material to detect acid vapors by naked eyes. However, the protonation would be prohibited in BTPQ and DBTPQ on account of the steric effect of tetraphenylethylene units linked to 5,8-positions of quinoxaline, so BTPQ and DBTPQ could not detect acid. Interestingly, the solid emitting colors of BTPQ as well as DBTPQ were quite different before and after grinding, exhibiting mechanochromic properties. The as-prepared crystal of BTPQ emitting blue light under UV irradiation could be changed into amorphous powder with bluish green emission. The XRD patterns suggested that the mechanochromism was originated from the transition between the crystalline and amorphous states. Such mechanochromism was reversible under the treatment of grinding and heating/fuming with DCM. In the experiment, the researchers used many compounds, for example, 5,8-Dibromoquinoxaline (cas: 148231-12-3Recommanded Product: 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, 浼?hydroxyketone, 浼?methyl ketone. 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.Recommanded Product: 148231-12-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Metal-catalyzed oxidations. Part 6. Molybdenum-catalyzed olefin epoxidation: ligand effects was written by Thiel, Werner R.;Eppinger, Joerg. And the article was included in Chemistry – A European Journal in 1997.Electric Literature of C7H8N2O2 This article mentions the following:

0E synthesized substituted pyrazolylpyridine ligands to examine their donor properties by spectroscopic (IR, NMR) and computational (AM1) methods. The influence of the substitution patterns on spectroscopic and thermodn. features of molybdenum oxobisperoxo complexes [(L-L)MoO(O₂)₂] [L-L = 2-(1-alkyl-3-pyrazolyl)pyridine/pyrazine] correlates with the activities of the complexes in catalytic olefin epoxidation reactions. This further proof for the relation between the Lewis acidity and the catalytic activity of epoxidation catalysts supports a reaction mechanism in which the peroxo complex activates the oxidizing agent (H₂O₂, ROOH) instead of directly transferring an oxygen atom from a 鐣?sup>2-peroxo ligand to the olefin. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Electric Literature of C7H8N2O2).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) 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 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.Electric Literature of C7H8N2O2

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Syntheses of pyrazines. I was written by Tsai, Songchuan;Chang, Zhangfu;Wang, Wingziang;Chang, Ming;Ji, Suping. And the article was included in Nanjing Daxue Xuebao, Ziran Kexue in 1984.Application of 6924-68-1 This article mentions the following:

Six alkylpyrazines I (R = Me, Et; R¹ = Et, CHMe₂; R² = H, Me) were prepared by the cyclocondensation of H₂NCHR²CH₂NH₂ and RCOCOR¹, followed by catalytic dehydrogenation. Oxidation of I (R = Me, Et, R¹ = Et, R² = H, Me) with Na₂Cr₂O₇ and AcOH gave acetylpyrazines I (R = Me, Et, R¹ = Ac, R² = H, Me). 2-Acetylpyrazine was prepared by the cyclocondensation of o-C₆H₄(NH₂)₂ with glyoxal to give quinoxaline, then oxidation and decarboxylation to pyrazinecarboxylic acid, followed by esterification and Claisen condensation with AcOEt. All pyrazines prepared have unique aroma useful for food flavorings. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Application of 6924-68-1).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) belongs to pyrazine derivatives. Pyrazines are volatile compounds that are used in the cosmetic, food, flavor, and fragrance industries. Pyrazine-based skeletons were incorporated into agents targeting a range of ailments. Many derivatives were synthesized and evaluated as potential cancer treatments.Application of 6924-68-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis and spectroscopic study of three new oxadiazole derivatives with detailed computational evaluation of their reactivity and pharmaceutical potential was written by Mary, Y. Sheena;Miniyar, Pankaj B.;Mary, Y. Shyma;Resmi, K. S.;Panicker, C. Yohannan;Armakovic, Stevan;Armakovic, Sanja J.;Thomas, Renjith;Sureshkumar, B.. And the article was included in Journal of Molecular Structure in 2018.Synthetic Route of C7H8N2O2 This article mentions the following:

Local reactivity properties and potential for application in new pharmaceutical compounds have been addressed for the three newly synthesized oxadiazole derivatives 2-(5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl)pyrazine (ORTHONITRO), 2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl)pyrazine (METANITRO) and 2-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)pyrazine (PARANITRO), by application of computational mol. modeling. Within the framework of d. functional theory (DFT) this study encompassed calculations of mol. electrostatic potential (MEP), average local ionization energies (ALIE) and bond dissociation energies for hydrogen abstraction (H-BDE). MD simulations have been used in order to assess the influence of water and to identify the atoms of these mols. with preference towards the interaction with water mols. Mol. docking procedure has been applied in order to check the binding activity of these derivatives against the Glucan endo-1.6-beta-glucosidase inhibitor, Acrocylindropepsin inhibitor and Chymosin inhibitor proteins. The pharmaceutical potential of these derivatives has been assessed by the calculations of the well-established drug likeness parameters. A strong out-of-plane CH mode of the Ph rings are observed at 769 cm^-1 for ORTHONITRO, 768 cm^-1 for METANITRO and at 848 cm^-1 for PARANITRO in the IR spectrum as expected for substituted benzenes. The VCD signals, corresponding to C=N and NO₂ modes of the title compounds are good markers for assigning of absolute configuration. In the title compounds, in ORTHONITRO, the oxadiazole ring is tilted from the Ph and pyrazine ring while for METANITRO and PARANITRO, there is a planar orientation. The first hyperpolariazabilities of ORTHONITRO, METANITRO and PARANITRO are resp., 34.83, 54.50 and 174.05 times that of urea. For all the compounds, HOMO is delocalized over the pyrazine and oxadiazole rings, while LUMO is delocalized over whole mol., except pyrazine ring of ORTHONITRO, over Ph ring and NO₂ group of METANITRO and in the entire mol. of PARANITRO. The title compounds are docked with the proteins, Glucan endo-1.6-beta-glucosidase inhibitor, Acrocylindropepsin inhibitor and Chymosin inhibitor and METANITRO exhibits more inhibitory activity against the receptors than the other ligands. The results obtained from anti-TB activity are more promising as the compounds were found to be more potent than reference standard, ORTHONITRO (MIC = 1.6 娓璯/mL), METANITRO (MIC = 0.8 娓璯/mL), PARANITRO (MIC = 1.6 娓璯/mL), streptomycin (MIC = 6.2 娓璯/mL) and pyrazinamide (MIC = 3.1 娓璯/mL). In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Synthetic Route of C7H8N2O2).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) belongs to pyrazine derivatives. Pyrazines are volatile compounds that are used in the cosmetic, food, flavor, and fragrance industries. A large number of pyrazine derivatives are known for their antitumor, antibiotic, anticonvulsant, antituberculosis, and diuretic activities.Synthetic Route of C7H8N2O2

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Stabilizing biochemically important intermediates through metal coordination. 5,8-Bis(trimethylsilyl)-5,8-dihydropteridine and its deaza derivative was written by Bessenbacher, Christian;Kaim, Wolfgang. And the article was included in Journal of Organometallic Chemistry in 1989.Reference of 322-46-3 This article mentions the following:

Reductive trimethylsilylation of pteridine and its deaza derivatives 1,4,6- and 1,4,5-triazanaphthalene and quinoxaline yields the primary reduced forms of these heterocycles, which contain the 1,4-dihydro-1,4-diazine ring with 8 conjugated 锜?electrons as the only low mol. weight products. Although the organometallic substituents stabilize these biochem. important yet normally short-lived dihydro forms and so allow unambiguous characterization by NMR, the non-crystalline, colored compounds are still highly reactive. Unexpectedly, the deaza derivatives prove to be less electron-rich than the silylated dihydropteridine despite a clear increase in the electron d. in the aromatic ring. The characteristic conformational flexibility of these intermediates is responsible for this inverse annulation effect. Reductive trimethylsilylation of 1,5-naphthyridine yields the 1-trimethylsilyl-1,4-dihydro derivative as the major product. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Reference of 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. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.Reference of 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis of organosilicon polymers containing donor-acceptor type 锜?conjugated units and their application to dye-sensitized solar cells was written by Ohshita, Joji;Kangai, Sinji;Yoshida, Hiroto;Kunai, Atsutaka;Kajiwara, Shotaro;Ooyama, Yousuke;Harima, Yutaka. And the article was included in Journal of Organometallic Chemistry in 2007.Reference of 148231-12-3 This article mentions the following:

Novel organosilicon polymers with donor-acceptor type 锜?conjugated units in the backbone were prepared by Stille coupling reaction of bis(tributylstannylthienyl)silanes with diiodoquinoxaline, benzothiadiazole, and benzoselenadiazole. De-halogenative copolymerization of di(bromothienyl)silanes and dibromoquinoxaline which gave the corresponding random copolymer was also studied. Applications of these polymers to dye-sensitized solar cells (DSSCs) were examined and the polymer containing benzoselenadiazole units as the acceptor had the best sensitizer performance. In the experiment, the researchers used many compounds, for example, 5,8-Dibromoquinoxaline (cas: 148231-12-3Reference of 148231-12-3).

5,8-Dibromoquinoxaline (cas: 148231-12-3) belongs to pyrazine derivatives. Pyrazine is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.Reference of 148231-12-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reaction of 1-ethoxyalylmethylpyrido[2,3-b]pyrazinium bromide with ammonium acetate: synthesis of imidazo[1′,2′:1,2]pyrido[5,6-b]pyrazines was written by Blache, Yves;Gueiffier, Alain;Chavignon, Olivier;Elhakmaoui, Ahmed;Viols, Henry;Teulade, Jean Claude;Milhavet, Jean Claude;Dauphin, Gerard;Chapat, Jean Pierre. And the article was included in Heterocycles in 1994.Recommanded Product: Pyrido[2,3-b]pyrazine This article mentions the following:

The synthesis of some imidazo[1,2′:1,2]pyrido[5,6-b]pyrazines I (R¹ = H, Me, R² = H; R¹ = R² = Me) by treatment of quaternary salts of pyrido[2,3-b]pyrazines II (R³ = H) with ammonium acetate in AcOH media is described. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Recommanded Product: Pyrido[2,3-b]pyrazine).

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 large number of pyrazine derivatives are known for their antitumor, antibiotic, anticonvulsant, antituberculosis, and diuretic activities.Recommanded Product: Pyrido[2,3-b]pyrazine

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Self-consistent field molecular orbital calculations of ultraviolet electronic spectra of azanaphthalenes with the variable 灏?approximation was written by Tinland, Bernard. And the article was included in Theoretica Chimica Acta in 1967.Product Details of 322-46-3 This article mentions the following:

The stable crystal field M.O. calculations of uv electronic spectra of 10 azonaphthalenes with the variable 灏?approximation (K. Nishimoto, et al., 1966) are presented. The transition energies and bond lengths of these mols. were calculated and the results are in satisfactory agreement with experiment In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Product Details of 322-46-3).

Pyrido[2,3-b]pyrazine (cas: 322-46-3) 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. Pyrazines are chemical compounds (technically called 閳ユ笗ethoxypyrazines閳? found in grape skin and stems that are responsible for many 閳ユ笀reen閳?flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.Product Details of 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem