Category: Pyrazines

Dramatically enhanced fluorescence of heteroaromatic chromophores upon insertion as spacers into oligo(triacetylene)s was written by Edelmann, Michael J.;Raimundo, Jean-Manuel;Utesch, Nils F.;Diederich, Francois. And the article was included in Helvetica Chimica Acta in 2002.SDS of cas: 148231-12-3 This article mentions the following:

In continuation of a previous study on the modulation of π-electron conjugation of oligo(triacetylene)s by insertion of central hetero-spacer fragments between two (E)-hex-3-ene-1,5-diyne ((E)-1,2-diethynylethene, DEE) moieties, trimeric hybrid oligomers (I; A = spacer, R = SiEt₃, SiMe₃) were prepared Spacers used were both electron-deficient (quinoxaline-based heterocycles, pyridazine) and electron-rich (2,2′-bithiophene, 9,9-dioctyl-9H-fluorene)chromophores. With a dipyridophenazine spacer, transition metal complexes were synthesized as potential precursors for nanoscale scaffolding based on both covalent acetylenic coupling and supramol. assembly. The UV/visible spectra revealed that the majority of spacers provided heterotrimers featuring extended π-electron delocalization. The new hybrid chromophores show a dramatically enhanced fluorescence compared with the DEE dimer and homo-trimer. This increase in emission intensity appears as a general feature of these systems: even if the spacer mol. is nonfluorescent, the corresponding hetero-trimer may show a strong emission. The redox properties of the new hybrid chromophores were determined by cyclic voltammetry (CV) and rotating disk voltammetry (RDV). In each case, the first 1-electron reduction step in the hetero-trimers appeared anodically shifted compared with DEE dimer and homo-trimer. With larger spacer chromophore extending into two dimensions, the anodic shift (by 240-490 mV) seems to originate from inductive effects of the two strongly electron-accepting DEE substituents rather than from extended π-electron conjugation along the oligomeric backbone, as had previously been observed for DEE substituted porphyrins. In the experiment, the researchers used many compounds, for example, 5,8-Dibromoquinoxaline (cas: 148231-12-3SDS of cas: 148231-12-3).

5,8-Dibromoquinoxaline (cas: 148231-12-3) 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 undergo nearly all of the same reactions as pyrimidines, from nucleophilic substitution (SNAr) to palladium-catalyzed cross coupling reactions.SDS of cas: 148231-12-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Hydrophobicity parameters determined by reversed-phase liquid chromatography. I. Relationship between capacity factors and octanol-water partition coefficients for monosubstituted pyrazines and the related pyridines was written by Yamagami, Chisako;Ogura, Tamaki;Takao, Narao. And the article was included in Journal of Chromatography in 1990.Application of 6924-68-1 This article mentions the following:

The capacity factors (k‘) of monosubstituted pyrazines and 2-substituted pyridines were measured on a Capcellpack C₁₈ column using methanol-buffer (pH 9.2) mobile phases of different compositions, and the relationship between log P (n-octanol-water partition coefficient) and log k‘ was analyzed. In all instances the amphiprotic substituents were eluted faster than expected on the assumption of log P-log k‘ linearity, reflecting that these groups act as hydrogen donors. For other substituents, a good linear relationship between log P and log k‘ was obtained with eluents containing 50-70% (volume/volume) of methanol. However, as the methanol content decreased, linearity no longer held and correction terms for the electronic effects and specific effects attributed to ester and amide groups were required. The relationship between log k‘ (pyrazine) and log k‘ (pyridine) was studied by applying a modified bidirectional Hammett-type correction for the component in π-value attributable to electronic effects of substituents and aza functions on the hydrogen-bonding solvation effect. The retention behavior changes systematically with changes in mobile phase composition 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 part of several biologically active polycyclic compounds; examples are quinoxalines, phenazines; and the bio-luminescent natural products pteridines, flavins, and their derivatives. A number of pyrazine-based derivatives were used as dyes or fluorescent probes.Application of 6924-68-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis of the novel ligustrazine derivatives and their protective effect on injured vascular endothelial cell damaged by hydrogen peroxide was written by Liu, Xinyong;Zhang, Rui;Xu, Wenfang;Li, Chaowu;Zhao, Quanqin;Wang, Xingpo. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2003.Formula: C8H12N2O This article mentions the following:

A series of novel 2-acyloxymethyl-3,5,6-trimethylpyrazine derivatives, e.g. I (R = Ph), was designed and synthesized. Most compounds were found to be 1.5-4.5-fold higher potency than tetramethylpyrazine (TMP) in stimulating the proliferation of normal vascular endothelial cells and in protecting against hyperoxic acute injury. The most active one is I (RCO = 2-nicotinoyl) exhibiting the maximum proliferation rate (P_max) of 88.57% at the concentration of 0.1 mmol L^-1. Structure-activity relationships of these compounds were discussed. 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 an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, α-hydroxyketone, α-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.Formula: C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis and anti-platelet aggregation activity evaluation of ligustrazine derivatives was written by Fan, Lingling;Li, Yi;Wu, Xiaofang;Li, Yong;Zhang, Jue. And the article was included in Huaxue Tongbao in 2018.Safety of (3,5,6-Trimethylpyrazin-2-yl)methanol This article mentions the following:

Using ligustrazine (TMP) and o-phenylenediamine as raw materials, seven derivatives were synthesized via KMnO₄ oxidation, esterification, cyclization and reduction The structures were confirmed by ¹H NMR, ¹³C NMR and HRMS. The in vitro anti-platelet aggregation activities of the target compounds have been preliminarily tested by the Born turbidimetric method, and the exptl. results showed that compounds 3 (IC₅₀ = 0.23 mmol/L) and 7 (IC₅₀ = 0.27mmol/L) have significant inhibitory activity of against ADP (ADP) induced platelet aggregation, higher than that of ligustrazine (IC₅₀ = 0.42mmol/L). 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. Pyrazines are part of several biologically active polycyclic compounds; examples are quinoxalines, phenazines; and the bio-luminescent natural products pteridines, flavins, and their derivatives. Pyrazines undergo nearly all of the same reactions as pyrimidines, from nucleophilic substitution (SNAr) to palladium-catalyzed cross coupling reactions.Safety of (3,5,6-Trimethylpyrazin-2-yl)methanol

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Antioxidative and thrombolytic TMP nitrone for treatment of ischemic stroke was written by Sun, Yewei;Jiang, Jie;Zhang, Zaijun;Yu, Pei;Wang, Linda;Xu, Changlin;Liu, Wei;Wang, Yuqiang. And the article was included in Bioorganic & Medicinal Chemistry in 2008.COA of Formula: C8H12N2O This article mentions the following:

Ischemic stroke results from brain blood vessel blockage by thrombus, and produces neuronal cell damage and death. While thrombolytic therapy with tPA has achieved some success in clinic, the strategy of using neuroprotective agents to treat ischemic stroke has been disappointing thus far. In the present work, the authors synthesized TBN, a derivative of the clin. useful stroke drug TMP armed with a powerful free radical-scavenging nitrone moiety. TBN retains the thrombolytic activity of the parent TMP and possesses strong antioxidative properties. TBN demonstrates significant activity in the rat MCAo stroke model. The results suggest that design of mols. possessing both thrombolytic and neuroprotective properties may be a novel strategy for effective stroke therapeutics. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3COA of Formula: C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) 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.COA of Formula: C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Preparation and investigation of the spectral and electrochemical properties of mixed-ligand ruthenium(II) complexes containing 1,8-naphthyridines was written by Staniewicz, Robert J.;Sympson, Robert F.;Hendricker, David G.. And the article was included in Inorganic Chemistry in 1977.Related Products of 322-46-3 This article mentions the following:

Mixed-ligand complexes of the form Ru(bpy)2L2+ and Ru(phen)2L2+, L = 1,8-naphthyridine (napy), 2,7-dimethyl-1,3-naphthyridine, 2-methyl-1,8-naphthyridine, and pyrido[2,3-b]pyrazine, and bpy is 2,2′-bipyridine and phen is 1,10-phenanetroline were prepared and isolated as their PF6- salts. The formulations were confirmed by elemental and anal. and conductivity measurements while the purity of the compounds was judged by the single maximum observed in the a.c. polarograms. The solution spectra of the mixed-ligand complexes are characterized by a high-intensity (ε âˆ?04) metal-to-ligand charge-transfer band at âˆ?50 nm and π â†?π* intraligand UV transitions. The energies and intensities of these absorptions are compared with previously reported Ru(byp)2X22+ complexes. The reduction potentials (Ru3+/Ru2+) for the napy mixed-ligand complexes were determined using both cyclic voltammetry and a.c. polarog. and the reversibility of the electrochem. couples was established. The E1/2 values do not vary greatly from those observed for the (phen)3- and (bpy)3Ru(II) complexes thus indicating that the stability of the Ru(II) state has not been significantly altered by the replacement of a phen or bpy with a napy type ligand. In the experiment, the researchers used many compounds, for example, Pyrido[2,3-b]pyrazine (cas: 322-46-3Related Products 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. Pyrazine-based skeletons were incorporated into agents targeting a range of ailments. Many derivatives were synthesized and evaluated as potential cancer treatments.Related Products of 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Ligustrazine derivatives. Part 4: Design, synthesis, and biological evaluation of novel ligustrazine-based stilbene derivatives as potential cardiovascular agents was written by Deng, Lijuan;Guo, Xiuli;Zhai, Li;Song, Yuning;Chen, Hongfei;Zhan, Peng;Wu, Jingde;Liu, Xinyong. And the article was included in Chemical Biology & Drug Design in 2012.Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol This article mentions the following:

A series of novel stilbene derivatives containing ligustrazinyl moiety was designed, synthesized, and assayed for their protective effects on damaged endothelial cells. The results showed that most ligustrazinyl stilbene derivatives exhibited high protective effects on the human umbilical vascular endothelial cells (HUVECs) damaged by hydrogen peroxide in comparison with Ligustrazine. Structure-activity relationships were briefly discussed. 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 derivatives have antitumor, antibiotic, anticonvulsant, antituberculous and diuretic effects as well as kinase, enzymatic and potent tubulin and FtsZ polymerization inhibitory activities. Pyrazines undergo nearly all of the same reactions as pyrimidines, from nucleophilic substitution (SNAr) to palladium-catalyzed cross coupling reactions.Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Calculation of electronic spectra of azabenzenes and azanaphthalenes by a simplified version of the Pariser-Parr-Pople method was written by Favini, Giorgio;Vandoni, Ida;Simonetta, Massimo. And the article was included in Theoretica Chimica Acta in 1965.SDS of cas: 322-46-3 This article mentions the following:

The simplified version given by Heilbronner, et al. (CA 60, 15160h) of the Pariser-Parr-Pople treatment was used to calculate transition energies and intensities of the π – π^* bands in the electronic spectra of 31 azines (azabenzenes and azanaphthalenes). A comparison with exptl. data results in a better agreement than for the complete treatment. 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 is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. 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.SDS of cas: 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In Silico Design of 2D and 3D Covalent Organic Frameworks for Methane Storage Applications was written by Mercado, Rocio;Fu, Rueih-Sheng;Yakutovich, Aliaksandr V.;Talirz, Leopold;Haranczyk, Maciej;Smit, Berend. And the article was included in Chemistry of Materials in 2018.Recommanded Product: 5,8-Dibromoquinoxaline This article mentions the following:

We present a database of 69,840 largely novel covalent organic frameworks assembled in silico from 666 distinct organic linkers and 4 established synthetic routes. Due to their light weights and high internal surface areas, the frameworks are promising materials for CH₄ storage applications. To assess their CH₄ storage performance, we used grand-canonical Monte Carlo simulations to calculate their deliverable capacities. We demonstrate that the best structure, composed of C-C bonded triazine linkers in the tbd topol., has a predicted 65-bar deliverable capacity of 216 v STP/v, better than the best CH₄ storage materials published to date. Using our approach, we also discovered other high-performing materials with 300 structures with calculated deliverable capacities >190 v STP/v and 10% of these outperforming 200 v STP/v. To encourage screening studies of these materials for other applications, all structures and their properties were made available on the Materials Cloud. In the experiment, the researchers used many compounds, for example, 5,8-Dibromoquinoxaline (cas: 148231-12-3Recommanded Product: 5,8-Dibromoquinoxaline).

5,8-Dibromoquinoxaline (cas: 148231-12-3) 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 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.Recommanded Product: 5,8-Dibromoquinoxaline

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Ligustrazine derivatives. Part 3: Design, synthesis and evaluation of novel acylpiperazinyl derivatives as potential cerebrocardiac vascular agents was written by Cheng, Xian-Chao;Liu, Xin-Yong;Xu, Wen-Fang;Guo, Xiu-Li;Zhang, Ning;Song, Yu-Ning. And the article was included in Bioorganic & Medicinal Chemistry in 2009.SDS of cas: 75907-74-3 This article mentions the following:

A series of novel acylpiperazinyl Ligustrazine derivatives was designed, synthesized, and their protective effects on damaged ECV-304 cells and antiplatelet aggregation activities were evaluated. The results showed that compound I (R = salicyloyl) displayed most potential protective effects on the ECV-304 cells damaged by hydrogen peroxide, and compound I (R = acetylsalicyloyl) was found to be the most active antiplatelet aggregation agent. Structure-activity relationships were briefly discussed. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3SDS of cas: 75907-74-3).

(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. 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.SDS of cas: 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem