Category: Pyrazines

Pi-electron delocalization in aza derivatives of naphthalene and indole was written by Mohajeri, Afshan;Shahamirian, Mozhgan. And the article was included in Computational & Theoretical Chemistry in 2011.Reference of 322-46-3 This article mentions the following:

The influence of increasing number of nitrogens and their sequences on π-electron delocalization of aza derivatives of naphthalene and indole was studied using different quant. descriptors including the geometry-based harmonic oscillator model of aromaticity (HOMA), magnetic index nucleus independent chem. shift (NICS) and electronic indexes. Also the authors used HOMO-LUMO gap and anisotropy of magnetic susceptibility as global descriptors. N-N bond destabilizes both endosubstituted naphthalenes and indoles and the most stable isomers are those having smallest number of such units. All studied indexes except HOMA indicate aromaticity lowering with an increase of the number of N atoms in a ring, however, the anomaly high aromatic characters are observed for the cases when N-N bond is formed. Anal. of at. charge d. shows that the maximum local aromaticity belongs to position isomer in which the average over at. charges on heteroatoms is less in the individual rings. 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 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.Reference of 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Antilipolytic activity of a series of pyrazine-N-oxides was written by Ambrogi, Vittorio;Cozzi, Paolo;Sanjust, Paolo;Bertone, Leone;Paolo Lovisolo, Pier;Briatico Vangosa, Gabriella;Angelucci, Romano. And the article was included in European Journal of Medicinal Chemistry in 1980.Recommanded Product: 89323-09-1 This article mentions the following:

Of the 45 pyrazinecarboxamide 4-oxides I (R = H, Cl, alkyl, NH₂, etc.; R¹ = H, Et; R² = H, OH, Et, etc.; or NR¹,R² = morpholino) and pyrazine 4-oxide carboxylic acids and esters II (R = H, Me, Cl, etc.; R¹ = H, Me, Et, etc.) synthesized, 3 showed pronounced and lasting antilipolytic activity in rats. The 3 were: 5-methylpyrazine-2-carboxylic acid 4-oxide (II; R = 5-Me; R¹ = H) [51037-30-0], 5-methylpyrazine-2-carboxylic acid diethylamide 4-oxide (I; R = 5-Me; R¹ = R² = Et) [51037-28-6], and allyl 5-methylpyrazine-2-carboxylate-4-oxide (II; R = 5-Me; R¹ = CH₂CH:CH₂) [74416-40-3]. The presence of a Me group at position 5 in the mol. was indispensable for pharmacol. activity. Esterification of the carboxyl in position 2 or its substitution with a primary, secondary, or tertiary carboxamide group did not cause notable changes in activity. In the experiment, the researchers used many compounds, for example, 5-Aminopyrazine-2-carboxamide (cas: 89323-09-1Recommanded Product: 89323-09-1).

5-Aminopyrazine-2-carboxamide (cas: 89323-09-1) 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.Recommanded Product: 89323-09-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Biochemical identification of two types of phenamil binding sites associated with amiloride-sensitive sodium channels was written by Barbry, Pascal;Chassande, Olivier;Duval, Daniele;Rousseau, Bernard;Frelin, Christian;Lazdunski, Michel. And the article was included in Biochemistry in 1989.Safety of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate This article mentions the following:

The biochem. basis for the existence of distinct forms of the epithelium Na⁺ channel that differ in their sensitivity to amiloride was analyzed by using phenamil, the most potent inhibitor known so far for the epithelium Na⁺ channel. [³H]Phenamil of high radioactive specific activity (30 Ci/mmol) was prepared and used to titrate [³H]phenamil-binding sites in pig kidney membranes. Kinetic experiments, equilibrium binding studies, and competition experiments indicated the presence in crude membrane preparations of 12 classes of independent binding sites. The 1st binding site was characterized by a high affinity for phenamil (dissociation constant 1 (K_d1) = 0.4 nM) and for amiloride (K_d1 = 0.1 μM). The 2nd binding site recognized phenamil and amiloride with lower affinities (K_d2(phenamil) = 28 nM, K_d2(amiloride) = 4 μM). The ratio of the resp. amounts of low- and high-affinity binding sites was 14 in different membrane preparations (range: 6-22). The 2 types of binding sites for [³H]phenamil copurified and were still observed after purification of the epithelium Na⁺ channel to homogeneity. Thus, â‰? types of pharmacol. distinguishable Na⁺ channels exist in the kidney. They correspond either to 2 isoforms of the apical Na⁺ channel or to 1 single type of channel under 2 different states of covalent regulation. In the experiment, the researchers used many compounds, for example, Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate (cas: 1458-01-1Safety 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. 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). 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.Safety of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Redox-sensitive carrier-free nanoparticles self-assembled by disulfide-linked paclitaxel-tetramethylpyrazine conjugate for combination cancer chemotherapy was written by Zou, Liang;Liu, Xiaowei;Li, Jingjing;Li, Wei;Zhang, Lele;Fu, Chaomei;Zhang, Jinming;Gu, Zhongwei. And the article was included in Theranostics in 2021.COA of Formula: C8H12N2O This article mentions the following:

Combinations of two or more therapeutic agents targeting different signaling pathways involved in tumor progression can have synergistic anticancer effects. However, combination chemotherapies are greatly limited by the different pharmacokinetics, tumor targeting, and cellular uptake capacities of the combined drugs. We have previously demonstrated the potential synergistic efficacy of paclitaxel (PTX) and the natural anti-angiogenic agent tetramethylpyrazine (TMP) for suppressing ovarian carcinoma growth. An efficient, facile, and smart nanosystem to deliver PTX and TMP simultaneously in vivo is greatly desired. We constructed a redox-sensitive nanosystem based on the amphiphilic PTX-ss-TMP conjugate, in which PTX and TMP are linked by a disulfide bond. We characterized the structure of the drug conjugate by ¹H NMR and LC-MS, and then prepared PTX-ss-TMP NPs by a one-step nanopptn. method. We investigated the redox sensitivity, tumor-targeting ability, anticancer efficacy, and anti-angiogenesis activity of PTX-ss-TMP NPs in vitro and in vivo. The amphiphilic PTX-ss-TMP conjugate readily self-assembled into stable nanoparticles in aqueous solution with a low critical association concentration of 1.35 μg/mL, well-defined spherical structure, small particle size (152 nm), high drug loading, redox-responsive drug release, high biocompatibility, and high storage stability. In cancer cells pretreated with GSH-OEt, PTX-ss-TMP NPs exhibited higher cytotoxicity, apoptosis rate, and cell-cycle arrest than monotherapy or combination therapy with free drugs, which was attributed to their improved cellular uptake and rapid intracellular drug release. Addnl., PTX-ss-TMP NPs also had a stronger anti-angiogenesis effect in HUVECs than free drug, which was mediated by VEGFR2-involved downstream signals. Finally, PTX-ss-TMP NPs showed tumor-specific accumulation and excellent antitumor activity in A2780 xenograft mice compared with free drug. These in vitro and in vivo results provide clear evidence that this redox-responsive carrier-free nanosystem with intrinsic amphiphilicity has great potential for combination cancer chemotherapy. 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. Pyrazine is an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, α-hydroxyketone, α-methyl ketone. Pyrazine-based skeletons were incorporated into agents targeting a range of ailments. Many derivatives were synthesized and evaluated as potential cancer treatments.COA of Formula: C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Practical Approach for the Preparation of α-Keto Amides by Direct Aminocarbonylation of Carboxylic Esters with a Carbamoylsilane was written by Han, Yuling;Han, Shenghua;Ma, Jiangwen;Li, Weidong;Chen, Jianxin. And the article was included in Synlett in 2020.Related Products of 6924-68-1 This article mentions the following:

A novel and practical method has been developed for the preparation of α-keto amides e.g., Me 3-[(dimethylcarbamoyl)carbonyl]benzoate by a catalyst-free aminocarbonylation of carboxylic esters RC(O)OR¹ (R = CF₃, 4-nitrophenyl, 6-fluoropyridin-3-yl, pyrazin-2-yl, etc.; R¹ = Me, Et, Ph) with N,N-dimethylcarbamoyl(trimethyl)silane under neutral conditions. A new protocol for the synthesis of N,N-dimethyl-β-ethoxy-α,β-dioxo-propionamide was also developed by using this method. In the case of di-Et oxalate, only one ester group reacted selectively with 1.2 equiv of the N,N-dimethylcarbamoyl(trimethyl)silane, leading to the formation of N,N-dimethyl-β-ethoxy-α,β-dioxo-propionamide. The reaction was suitable for aryl, hetaryl, or open-chain esters containing strongly electron-withdrawing groups. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Related Products of 6924-68-1).

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. 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.Related Products of 6924-68-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Excited singlet state absorption spectra and relaxation kinetics of the azanaphthalenes was written by Boldridge, David W.;Scott, Gary W.. And the article was included in Journal of Chemical Physics in 1986.Related Products of 322-46-3 This article mentions the following:

Picosecond excited-state singlet-singlet absorption spectra (S_n â†?S₁) and excited-state decay kinetics are reported for several diazanaphthalenes and a triazanaphthalene in room temperature solution New S_n (¹nπ^*) state energies were obtained empirically from these spectra. INDO-PSDCI mol. calculations were used to confirm the S_n â†?S₁ nature of the excited state transitions observed Decay rates were calculated from models based on a semiempirical mol. formalism, and these calculated rates were compared with the observed ones. Agreement of the calculated and observed rates are good except in cases of substantial nπ^*-ππ^* mixing of the actual excited states and in a particular case of high mol. symmetry (1,5-naphthyridine). 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 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.Related Products of 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis of substituted pyrazines derived from pyrazinecarboxaldehyde and hydroxymethylpyrazine was written by Piera, F.;Seoane, E.;Mestres, R.. And the article was included in Anales de Quimica (1968-1979) in 1979.SDS of cas: 6924-68-1 This article mentions the following:

From pyrazinecarboxylic and 2,3-pyrazinedicarboxylic esters were prepared from their acids. Pyrazinecarboxaldehyde (I) was obtained by LiAlH₄ reduction of Me pyrazinecarboxylate (II). Pyrazinylacrylates were obtained by Wittig reactions of I and alkyl pryazinyl carbinols by Grignard reactions of I. Pyrazinylmethacrolein was prepared by reducing pyrazinylmethacrylate to the alc. and MnO₂ oxidation NaBH₄ reduction of II gave pyrazinemethanol which when mesylated underwent a variety of substitution reactions. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1SDS of cas: 6924-68-1).

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. A large number of pyrazine derivatives are known for their antitumor, antibiotic, anticonvulsant, antituberculosis, and diuretic activities.SDS of cas: 6924-68-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Scavenging action to hydroxyl free radical of ligustrazine and it’s derivatives was written by Bian, Xiaoli;Chen, Xuemin;Liu, Yanxia;Pan, Qing. And the article was included in Zhongguo Yiyuan Yaoxue Zazhi in 2003.Reference of 75907-74-3 This article mentions the following:

The hydroxyl free radical scavenging activity of ligustrazine and its derivatives (2-hydromethyl-3,5,6- trimethylpyrazine, tetramethylpyrazine-N-monoxygen and tetramethylpyrazine-N-dioxygen) were evaluated using Fenton reaction to assay and calculate the concentration of compounds for scavenging 50% of hydroxyl free radicals (EC₅₀). In scavenging action to ·OH, a significant difference was observes between the ligustrazine as well as its derivatives and benzoic acid and mannitol (P <0.01), however, there was no apparent difference between ligustrazine and its derivatives (P >0.05). Ligustrazine and its derivatives had strong scavenging action to hydroxyl free radical. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Reference of 75907-74-3).

(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. A number of pyrazine-based derivatives were used as dyes or fluorescent probes.Reference of 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Chemotherapeutic studies on schistosomiasis. XXXVI. Synthesis of 4-phenyl- and 4-allyl-5-(2-pyrazinyl)-1,2,4-triazole-3-thione derivatives was written by Xu, Maoli;Lei, Xinghan. And the article was included in Yaoxue Xuebao in 1985.Quality Control of Ethyl pyrazine-2-carboxylate This article mentions the following:

Twenty-eight title compounds (I; R = Ph, allyl; R¹ = H, alkyl, acyl, dialkylaminomethyl, cyclic aminomethyl, etc.), effective schistosomicides at 1050 mg/kg in mice, were prepared Thus, heating 0.2 mol II (R² = EtO) with N₂H₄·H₂O in EtOH at 40-50° gave hydrazide II (R² = H₂NNH), which (0.075 mol) was heated with 0.09 mol PhNCS in EtOH at 110-50° to give 60-70% II (R² = PhNHCSNHNH) (III). Heating 0.08 mol III with 2 N NaOH at 70° gave 80-90% IV·Na (R = Ph), which (0.0045 mol) was heated with 0.0055 mol Me₂SO₄ in EtOH at 75° to give I (R = Ph, R¹ = H). In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Quality Control of Ethyl pyrazine-2-carboxylate).

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. A large number of pyrazine derivatives are known for their antitumor, antibiotic, anticonvulsant, antituberculosis, and diuretic activities.Quality Control of Ethyl pyrazine-2-carboxylate

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Hydrophobicity parameters determined by reversed-phase liquid chromatography. XIV. Application of a new hydrogen-accepting scale of monosubstituted pyrazines to analysis of the relationship between octanol-water partition coefficients and retention factors measured in different mobile phases was written by Yamagami, Chisako;Haraguchi, Miyako. And the article was included in Chemical & Pharmaceutical Bulletin in 2000.HPLC of Formula: 6924-68-1 This article mentions the following:

The authors recently proposed a new H-accepting scale, S_HA, for monosubstituted pyrazines, and demonstrated that this parameter works effectively in expressing the relation between log P (P: 1-octanol/H₂O partition coefficient) and log k’ (k’: retention factor derived from reversed phase liquid chromatog.) with aqueous MeOH solutions as the mobile phase, according to the equation: log k’ = a log P+ρσ₁+sS_HA+constant, where σ₁ represents the electronic substituent constant The authors have extended the same treatment to anal. of log k’ measured in mobile phases containing different organic modifiers such as 1-propanol, MeCN, and dioxane, and found that the above equation is still useful. By comparing the correlations obtained, the parameter S_HA could be universally used for representing the difference in H-bonding effects involved in different partitioning systems. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1HPLC of Formula: 6924-68-1).

Ethyl pyrazine-2-carboxylate (cas: 6924-68-1) 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.HPLC of Formula: 6924-68-1

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem