Category: Pyrazines

Synthesis, spectroscopic analyses (FT-IR and NMR), vibrational study, chemical reactivity and molecular docking study and anti-tubercular activity of condensed oxadiazole and pyrazine derivatives was written by El-Azab, Adel S.;Mary, Y. Sheena;Abdel-Aziz, Alaa A. M.;Miniyar, Pankaj B.;Armakovic, Stevan;Armakovic, Sanja J.. And the article was included in Journal of Molecular Structure in 2018.Application In Synthesis of Ethyl pyrazine-2-carboxylate This article mentions the following:

The Fourier transform IR spectra of the compounds 2-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazine (PHOXPY), 2-(5-styryl-1,3,4-oxadiazol-2-yl)pyrazine (STOXPY) and 2-(5-(furan-2-yl)-1,3,4-oxadiazol-2-yl)pyrazine (FUOXPY) have been recorded and the wavenumbers are computed at the d. functional theory level. The assignments of all the fundamental bands of each mol. are made using potential energy distribution. The computed values of dipole moment, polarizability and hyperpolarizability values indicate that the title mols. exhibit NLO properties. The HOMO and LUMO energies demonstrate the chem. stability of the mols. and NBO anal. is made to study the stability of mols. arising from hyper conjugative interactions and charge delocalization. Detailed computational anal. and spectroscopic characterization has been performed for three newly synthesized oxadiazole derivatives Obtained computational and exptl. results have been mutually compared in order to understand the influence of structural parts specific for each derivative From the MIC determination, MTb H37Rv was found to be sensitive to compounds, PHOXPY, STOXPY and FUOXPY. The results obtained from anti-TB activity are more promising as the compounds were found to be more potent than reference standards, streptomycin and pyrazinamide. Efforts were made in order to predict both global and local reactive properties of the title oxadiazole derivatives, including their sensitivity towards autoxidation mechanism and influence of water. The results obtained from anti-TB activity are more promising for the title compounds Interaction with representative protein Pterindeaminase inhibitor asricin A was also investigated using the mol. docking procedure. The docked ligands form stable complexes with the receptor ricin A and the docking results suggest that these compounds can be developed as new anti-cancer drugs. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Application In Synthesis of Ethyl pyrazine-2-carboxylate).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) 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.Application In Synthesis of Ethyl pyrazine-2-carboxylate

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

2,3-Dihydroxy-1,4-dioxane: a stable synthetic equivalent of anhydrous glyoxal was written by Venuti, Michael C.. And the article was included in Synthesis in 1982.Reference of 322-46-3 This article mentions the following:

1,4-Dioxane-2,3-diol (I) was obtained in 45% yield by treating aqueous glyoxal with ethylene glycol. I reacts as glyoxal with diamines, aldehydes, alcs., and thio ethers to give, e.g., quinoxaline, isonaphthazarin, and 2,5-bis(4-bromobenzoyl)thiophene. 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 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 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Determination and identification of amiloride in human urine by high-performance liquid chromatography and gas chromatography-mass spectrometry was written by Bi, Honggang;Cooper, Sam F.;Cote, Michel G.. And the article was included in Journal of Chromatography, Biomedical Applications in 1992.Application of 1458-01-1 This article mentions the following:

A simple and sensitive high-performance liquid chromatog. method was developed to screen and determine amiloride (I) in human urine. The detection limit of the method is 0.12 μg/mL and the recovery of amiloride from urine was 80.4-85.5% at different concentration The coefficients of variation were less than 2.8 and 4.4% for intra- and inter-assays, resp. Total urinary excretion of I in 24 h after oral administration of 5 mg or 15 mg of I ranged from 22.0 to 33.3% of the total dose for three different subjects. I could be detected in urine up to at least 44 h after a 5-mg dose and 72 h after a 15-mg dose. A gas chromatog.-mass spectrometric (GC-MS) confirmatory method was established based on the methanolysis of I to Me 3,5-diamino-6-chloropyrazinecarboxylate (II). The di-N-trimethylsilyl derivative of II showed very good GC-MS properties and provided reliable structure information for confirmation anal. of I. This is the first time that a reliable GC-MS method has been reported for the detection of urinary I. In the experiment, the researchers used many compounds, for example, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1Application of 1458-01-1).

Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1) 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.Application of 1458-01-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Optical and magnetic properties of the lowest triplet state of pyrido(2,3-b)pyrazine. An example of ³nπ* azanaphthalene was written by Yamauchi, Seigo;Hirota, Noboru. And the article was included in Journal of Physical Chemistry in 1987.Name: Pyrido[2,3-b]pyrazine This article mentions the following:

The lowest excited triplet (T₁) states of pyrido(2,3-b)pyrazine (PP; 1,4,5-triazanaphthalene) in 3 kinds of environments were studied by using various spectroscopic and magnetic resonance techniques. Phosphorescence emission and excitation spectra, triplet lifetimes, zero field splittings (zfs), and triplet sublevel properties were obtained. From the anal. of the results T₁ is ³nπ^* in character in a single crystal of durene and in EtOH, but it is ³ππ^* in trifluoroethanol. Observation of the ³nπ^* phosphorescence was made for the 1st time in azanaphthalenes, which provides direct information about ³nπ^* azanaphthalene. The 0-0 band and vibronic bands involving a’ vibrations are dominant in the phosphorescence spectrum. Large zfs and neg. D (≡ -311₂x; -3.1 GHz) were obtained. As for the sublevel properties T_z is the most active and T_x is inactive in both radiative and nonradiative processes, whereas T_y is moderately active in the T₁ ∼→ S₀ nonradiative decay process. These ³nπ^* properties are discussed in comparison with those of ³ππ^* PP and azanaphthalenes and ³nπ^* azabenzenes. Possible mechanisms to explain the radiative and nonradiative properties are given. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Name: Pyrido[2,3-b]pyrazine).

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. 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.Name: Pyrido[2,3-b]pyrazine

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Effects of 2-hydroxymethyl-3,5,6-trimethylpyrazine on cardiovascular system was written by Chen, Xue-Min;Cao, Yong-Xiao;Li, Guan-Wu;Lin, Zhang-Quan;Li, Xue-Fei;Liu, Jing. And the article was included in Zhongguo Yiyao Gongye Zazhi in 1998.Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol This article mentions the following:

The cardiovascular effects of 2-hydroxymethyl-3,5,6-trimethylpyrazine (I), one of the major metabolites of tetramethylpyrazine, were studied. I significantly prolonged cardiac potential lasting time and blood coagulating time in mice. It also significantly deduced the arterial blood pressure but had no effect on heart rates in rats. It was demonstrated that I improved the anoxemia-resistant ability and had the effects of antihypertension and anticoagulation. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine has the elements of symmetry for the point group D2h. It has three mutually perpendicular two-fold axes. It also has three mutually perpendicular planes of symmetry. As a result, pyrazine also has a centre of symmetry. Pyrazines are chemical compounds (technically called “methoxypyrazines”) found in grape skin and stems that are responsible for many “green” flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis, characterization and properties of aryl-fused bis-BN dihydropyrenes was written by Zhang, Jinyun;Liu, Fude;Sun, Zhe;Li, Chenglong;Zhang, Qian;Zhang, Chen;Liu, Zhiqiang;Liu, Xuguang. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2018.HPLC of Formula: 148231-12-3 This article mentions the following:

Aryl-fused bis-BN dihydropyrenes such as I were prepared from 5,8-dibromoquinoxaline (prepared in four steps from o-phenylenediamine), arylboronic acids, and PhBCl₂ using an amino-directed borylation reaction as the key step.. The UV/visible and fluorescence spectra, oxidation potentials, and optical bandgaps for four of the aryl-fused bis-BN dihydropyrenes were determined; their NICS aromaticities and the structures and energies of their HOMO and LUMO were calculated The aryl-fused bis-BN dihydropyrenes showed blue emission, and their phys. properties could be finely tuned through varying the fused aryl rings. The complexation of fluoride ion by the bis-BN dihydropyrenes was determined; the fluoride ion response depended strongly on the fused aryl rings. The structures of I and of two other aryl-fused bis-BN dihydropyrenes were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, 5,8-Dibromoquinoxaline (cas: 148231-12-3HPLC of Formula: 148231-12-3).

5,8-Dibromoquinoxaline (cas: 148231-12-3) 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.HPLC of Formula: 148231-12-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Design, Synthesis, and Structure-Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers: Drugs for Cystic Fibrosis and Chronic Bronchitis was written by Hirsh, Andrew J.;Molino, Bruce F.;Zhang, Jianzhong;Astakhova, Nadezhda;Geiss, William B.;Sargent, Bruce J.;Swenson, Brian D.;Usyatinsky, Alexander;Wyle, Michael J.;Boucher, Richard C.;Smith, Rick T.;Zamurs, Andra;Johnson, M. Ross. And the article was included in Journal of Medicinal Chemistry in 2006.Application In Synthesis of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate This article mentions the following:

Amiloride, the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogs of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent short-circuit current than amiloride. Compounds I [R = NH(CH₂)₄C₆H₄O(CH₂)₂OH-4, NH(CH₂)₄C₆H₄O(CH₂)₃OH-4, NH(CH₂)₄C₆H₄OCH₂CH(OH)CH₂OH-4 (both R and S isomers)] showed the greatest potency on ENaC with IC₅₀ values below 10 nM. A regioselective difference in potency was found, whereas no stereospecific difference in potency on ENaC was displayed. Lead compound I [R = NH(CH₂)₄C₆H₄OCH₂CH(OH)CH₂OH-4 (racemic)] was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC₅₀ value ever reported for an ENaC blocker. In the experiment, the researchers used many compounds, for example, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1Application In Synthesis of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate).

Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1) belongs to pyrazine derivatives. Pyrazine is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. A large number of pyrazine derivatives are known for their antitumor, antibiotic, anticonvulsant, antituberculosis, and diuretic activities.Application In Synthesis of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Preparation of poly(quinoxaline-5,8-diyl) derivatives by using zero-valent nickel complexes. Electrical and optical properties and light-emitting diodes was written by Kanbara, T.;Inoue, T.;Sugiyama, K.;Yamamoto, T.. And the article was included in Synthetic Metals in 1995.Application In Synthesis of 5,8-Dibromoquinoxaline This article mentions the following:

Dehalogenation polycondensation of 5,8-dibromoquinoxaline derivatives affords π-conjugated poly(quinoxaline-5,8-diyl) derivatives having high electron-accepting properties, and the polymers are easily converted into elec. conducting materials on chem. and electrochem. reductions The polymers having aromatic substituents show strong fluorescence and are useful materials to make light-emitting diodes. In the experiment, the researchers used many compounds, for example, 5,8-Dibromoquinoxaline (cas: 148231-12-3Application In Synthesis of 5,8-Dibromoquinoxaline).

5,8-Dibromoquinoxaline (cas: 148231-12-3) 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 “methoxypyrazines”) found in grape skin and stems that are responsible for many “green” flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.Application In Synthesis of 5,8-Dibromoquinoxaline

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Linear Conjugated Polymers for Solar-Driven Hydrogen Peroxide Production: The Importance of Catalyst Stability was written by Liu, Lunjie;Gao, Mei-Yan;Yang, Haofan;Wang, Xiaoyan;Li, Xiaobo;Cooper, Andrew I.. And the article was included in Journal of the American Chemical Society in 2021.Computed Properties of C8H4Br2N2 This article mentions the following:

Hydrogen peroxide (H₂O₂) is one of the most important industrial oxidants. In principle, photocatalytic H₂O₂ synthesis from oxygen and H₂O using sunlight could provide a cleaner alternative route to the current anthraquinone process. Recently, conjugated organic materials have been studied as photocatalysts for solar fuels synthesis because they offer synthetic tunability over a large chem. space. Here, we used high-throughput experiments to discover a linear conjugated polymer, poly(3-4-ethynylphenyl)ethynyl)pyridine (DE7), which exhibits efficient photocatalytic H₂O₂ production from H₂O and O₂ under visible light illumination for periods of up to 10 h or so. The apparent quantum yield was 8.7% at 420 nm. Mechanistic investigations showed that the H₂O₂ was produced via the photoinduced stepwise reduction of O₂. At longer photolysis times, however, this catalyst decomposed, suggesting a need to focus the photostability of organic photocatalysts, as well as the initial catalytic production rates. In the experiment, the researchers used many compounds, for example, 5,8-Dibromoquinoxaline (cas: 148231-12-3Computed Properties of C8H4Br2N2).

5,8-Dibromoquinoxaline (cas: 148231-12-3) belongs to pyrazine derivatives. Pyrazines are volatile compounds that are used in the cosmetic, food, flavor, and fragrance industries. 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.Computed Properties of C8H4Br2N2

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The preparation of 2-amino-5-pyrazinecarboxylic acid and its derivatives was written by Felder, E.;Pitre, D.;Grabitz, E. B.. And the article was included in Helvetica Chimica Acta in 1964.Synthetic Route of C5H6N4O This article mentions the following:

2-Acetamidoquinoxazoline was treated with KMnO₄ in small portions over 1 hr. at 90-5° to give 60% mono-K salt (I) of 2-acetamidopyrazine-5,6-dicarboxylic acid, m. 293° (decomposition). I (1 g.) refluxed 0.5 hr. in 35 ml. H₂O with 5 ml. N HCl gave 0.7 g. 2-aminopyrazine-5,6-dicarboxylic acid, m. 262° (decomposition), which, heated in H₂O 12 min. at 170-5°, gave 77% 2-aminopyrazine-5-carboxylic acid (II), m. 282-3° (decomposition); 70% Me ester (MeOH-HCl) m. 230-1°; Et ester m. 172-3°; amide m. 266-7°. II was treated in H₂SO₄ with NaNO₂ at 5° and the mixture heated 5 min. at 80° to give 2-hydroxypyrazine-5-carboxylic acid, m. 300°. In the experiment, the researchers used many compounds, for example, 5-Aminopyrazine-2-carboxamide (cas: 89323-09-1Synthetic Route of C5H6N4O).

5-Aminopyrazine-2-carboxamide (cas: 89323-09-1) 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 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.Synthetic Route of C5H6N4O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem