Category: Pyrazines

A platform for designing HIV integrase inhibitors. 2-Hydroxy-3-heteroaryl acrylic acid derivatives as novel HIV integrase inhibitor and modeling of hydrophilic and hydrophobic pharmacophores was written by Kawasuji, Takashi;Yoshinaga, Tomokazu;Sato, Akihiko;Yodo, Mitsuaki;Fujiwara, Tamio;Kiyama, Ryuichi. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Synthetic Route of C7H8N2O2 This article mentions the following:

The authors present a novel series of HIV integrase inhibitors, showing IC₅₀s ranging from 0.01 to over 370 μM in an enzymic assay. Furthermore, pharmacophore modeling study for the inhibitors was carried out to elucidate the structure-activity relationships. Finally, the authors found a 3D-pharmacophore model, which is composed of a hydrophilic and a hydrophobic domain, providing valuable information for designing other novel types of integrase inhibitors. 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. Pyrazine is a symmetrical molecule with point group D2h. Pyrazine is less basic than pyridine, pyridazine and pyrimidine. Pyrazines undergo nearly all of the same reactions as pyrimidines, from nucleophilic substitution (SNAr) to palladium-catalyzed cross coupling reactions.Synthetic Route of C7H8N2O2

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A systems biology approach to understanding the mechanisms of action of Chinese herbs for treatment of cardiovascular disease was written by Li, Bohui;Xu, Xue;Wang, Xia;Yu, Hua;Li, Xiuxiu;Tao, Weiyang;Wang, Yonghua;Yang, Ling. And the article was included in International Journal of Molecular Sciences in 2012.Synthetic Route of C8H12N2O This article mentions the following:

Traditional Chinese Medicine (TCM) involves a broad range of empirical testing and refinement and plays an important role in the health maintenance for people all over the world. However, due to the complexity of Chinese herbs, a full understanding of TCM’s action mechanisms is still unavailable despite plenty of successful applications of TCM in the treatment of various diseases, including especially cardiovascular diseases (CVD), one of the leading causes of death. Thus in the present work, by incorporating the chem. predictors, target predictors and network construction approaches, an integrated system of TCM has been constructed to systematically uncover the underlying action mechanisms of TCM. From three representative Chinese herbs, i.e., Ligusticum chuanxiong Hort., Dalbergia odorifera T. Chen and Corydalis yanhusuo WT Wang which have been widely used in CVD treatment, by combinational use of drug absorption, distribution, metabolism and excretion (ADME) screening and network pharmacol. techniques, we have generated 64 bioactive ingredients and identified 54 protein targets closely associated with CVD, of which 29 are common targets (52.7%) of the three herbs. The result provides new information on the efficiency of the Chinese herbs for the treatment of CVD and also explains one of the basic theories of TCM, i.e., “multiple herbal drugs can treat one disease”. The predicted potential targets were then mapped to target-disease and target-signal pathway connections, which revealed the relationships of the active ingredients with their potential targets, diseases and signal systems. This means that for the first time, the action mechanism of these three important Chinese herbs for the treatment of CVD is uncovered, by generating and identifying both their active ingredients and novel targets specifically related to CVD, which clarifies some of the common conceptions in TCM, and thus provides clues to modernize such specific herbal medicines. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Synthetic Route of C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazines are volatile compounds that are used in the cosmetic, food, flavor, and fragrance industries. 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.Synthetic Route of C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis and evaluation of new chalcones and oximes as anticancer agents was written by Bukhari, Syed Nasir Abbas. And the article was included in RSC Advances in 2022.Category: pyrazines This article mentions the following:

Complex illnesses, such as cancer, are often caused by many disorders, gene mutations, or pathways. Biol. pathways play a significant part in the development of these diseases. Multi-target directed ligands (MTDLs) have been used by medicinal chemists recently in an effort to find single mols. that can affect many targets concurrently. In this work, several chalcones containing the ligustrazine moiety were synthesized and tested for their in vitro anticancer activity and several cancer markers, including EGFR, BRAF^V600E, c-Met, and tubulin polymerization, in order to uncover multitarget bioactive compounds In assays using multiple cancer cell lines, the majority of the compounds examined showed strong anticancer activity against them. To synthesize oximes, all of the chalcones were used as precursors. The IC₅₀ values of two compounds ((1Z,2E)-1-(4-(5-Bromothiophen-2-yl)phenyl)-3-(3,5,6-trimethylpyrazin-2-yl)prop-2-en-1-one oxime and (1Z,2E)-1-(4-(4-Methylthiophen-2-yl)phenyl)-3-(3,5,6-trimethylpyrazin-2-yl)prop-2-en-1-one oxime) were found to be 0.87, 0.28, 2.43, 1.04 μM and (1Z,2E)-1-(4-(Thiophen-2-yl)phenyl)-3-(3,5,6-trimethylpyrazin-2-yl)prop-2-en-1-one oxime, 1.47, 0.79, 3.8, 1.63 μM resp., against A-375, MCF-7, HT-29 and H-460 cell lines. These IC₅₀ values revealed an excellent antiproliferative activity compared to those of the pos. control foretinib, (IC₅₀ = 1.9, 1.15, 3.97, and 2.86 μM). Careful examination of their structure and configuration revealed that both compounds had an oxime functional group with z configuration, in place of carbonyl functional group, along with a 2-Ph thiophenyl moiety with or without a bromo group at position-5. The possible binding pattern was implied by docking simulation, inferring the possibility of introducing interactions with the nearby tubulin chain. Since the novel structural trial has been conducted with a detailed structure activity relationship discussion, this work might stimulate new ideas in further modification of multitarget anti-cancer agents and therapeutic approaches. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Category: pyrazines).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) 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.Category: pyrazines

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Purity of intermediate ammoniate and its influence on quality of amiloride was written by Zhang, Shengqiang;Chen, Jianming;Yu, Wenxian;Jiang, Xinru. And the article was included in Zhongguo Yaoke Daxue Xuebao in 1995.Safety of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate This article mentions the following:

The purity of 3,5-diamino-6-chlor-2-methoxycarboxyl-pyrazine (ammoniate) was examine by HPLC. The chromatog. determination results of crude ammoniate were conformed by melting data. Ammoniate of high purity processed high m.p., the amiloride prepared with ammoniate of high purity had good quality. 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. 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. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.Safety of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The effect of molecular structure on the properties of quinoxaline-based molecules for OLED applications was written by Ledwon, Przemyslaw;Motyka, Radoslaw;Ivaniuk, Khrystyna;Pidluzhna, Anna;Martyniuk, Natalia;Stakhira, Pavlo;Baryshnikov, Glib;Minaev, Boris F.;Agren, Hans. And the article was included in Dyes and Pigments in 2020.SDS of cas: 148231-12-3 This article mentions the following:

Different donor-acceptor-donor (D-A-D) and donor-π-bridge-acceptor-π-bridge-donor (D-π-A-π-D) systems based on a quinoxaline acceptor are compared. A significant difference in electrochem. and photophys. properties was found depending on mol. structure. A luminescence shift from 539 up to 671 nm was observed upon extension of conjugation length. The studied compounds were tested in fluorescent organic light emitting diodes (OLEDs) demonstrating an external quantum efficiency up to 4.5% for a deep red nondoped device and 7% when doped into an exciplex host device. A quantum-chem. interpretation of the electroluminescence spectra for the fabricated OLEDs was carried out including modeling of excimers and exciplexes. 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. 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.SDS of cas: 148231-12-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Cinnolines. IV. Quaternization of 4-amino-6-chloro- and 6-chloro-4-phenoxycinnoline was written by Ames, D. E.. And the article was included in Journal of the Chemical Society in 1964.Name: 5-Aminopyrazine-2-carboxamide This article mentions the following:

The work of Simpson (CA 42, 2978e) on the quaternization of 4-amino-6-chlorocinnoline (I) has been reexamined, and alkylation is shown to occur at N-1 and N-2 on the basis of revised structures for the methylation products of 6-chloro-4-hydroxycinnoline. 6-Chloro-4-phenoxycinnoline, however, appears to form a methiodide only by reaction at N-2. In the experiment, the researchers used many compounds, for example, 5-Aminopyrazine-2-carboxamide (cas: 89323-09-1Name: 5-Aminopyrazine-2-carboxamide).

5-Aminopyrazine-2-carboxamide (cas: 89323-09-1) 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. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.Name: 5-Aminopyrazine-2-carboxamide

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis and biological evaluation of novel ‘CONH’ bridged indole and pyrazine derivatives was written by Kotnal, Ramaling B.. And the article was included in World Journal of Pharmaceutical Research in 2018.Safety of Ethyl pyrazine-2-carboxylate This article mentions the following:

A new series of N’-[(E)-Ph methylidene] pyrazine-2-carbohydrazide like 5-methyl-N’-[(1E)-(2-nitrophenyl)methylidene]pyrazine-2-carbohydrazide, N’-[(1E)-(2-hydroxyphenyl)methylidene]-5-methylpyrazine-2-carbohydrazide and N’-(2-oxo-1,2-dihydro-3H-indol-3-ylidene) pyrazine-2-carbohydrazide derivatives I (R = H, Me; R¹ = H, 5-CH₃, 7-F, 5-NO₂, 6-Br; R² = H, Me) were synthesized and evaluated for their antituberculosis, antibacterial and antifungal activities. All the synthesized compounds I were in good agreement with spectral anal. Three synthesized compounds I (R = Me, R¹ = F, R² = H; R = H, R¹ = F, R² = H; R = H, R¹ = 6-Br, R² = H) have shown significant anti-tubercular activity as compared to the reference drug. Compounds I (R = H, R¹ = 5-NO₂, R² = H; R = Me, R¹ = 5-NO₂, R² = H; R = H, R¹ = 6-Br, R² = H) shown good antibacterial activity against gram pos. bacteria and compounds I (R = H, R¹ = 7-F, R² = H; R = H, R¹ = 6-Br, R² = H) and 5-methyl-N’-[(1E)-(2-nitrophenyl)methylidene]pyrazine-2-carbohydrazide, N’-[(1E)-(2-hydroxyphenyl)methylidene]-5-methylpyrazine-2-carbohydrazide shown significant activity against gram neg. bacteria. Compounds I (R = Me, R¹ = F, R² = H; R = H, R¹ = 5-NO₂, R² = H; R = Me, R¹ = 6-Br, R² = H), 5-methyl-N’-[(1E)-(2-nitrophenyl)methylidene]pyrazine-2-carbohydrazide, N’-[(1E)-(2-hydroxyphenyl)methylidene]-5-methylpyrazine-2-carbohydrazide shown significant antifungal activity when compared with standard pyrazinamide, streptomycin, ciprofloxacin, fluconazole and were used as reference standard drug for the biol. activity, resp. The purity and structure confirmation of the synthesized compounds were done by TLC, IR and 1HNMR spectral 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. 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 large number of pyrazine derivatives are known for their antitumor, antibiotic, anticonvulsant, antituberculosis, and diuretic activities.Safety of Ethyl pyrazine-2-carboxylate

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Polarographic reduction of the azines was written by Wiberg, Kenneth B.;Lewis, Thomas P.. And the article was included in Journal of the American Chemical Society in 1970.HPLC of Formula: 322-46-3 This article mentions the following:

The polarog. reduction of many azines is irreversible, with the initial anion radical undergoing rapid reaction to give other products. Cyclic voltammetry is able in most cases to effect reoxidation of the anion radical before it reacts further, and gives the reversible electrode potential. The observed energy differences between azine and radical anion are well correlated with the results of CNDO (complete neglect of differential overlap) and SCF π-electron calculations 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. 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-based skeletons were incorporated into agents targeting a range of ailments. Many derivatives were synthesized and evaluated as potential cancer treatments.HPLC of Formula: 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A Predictive Model Towards Site-Selective Metalations of Functionalized Heterocycles, Arenes, Olefins, and Alkanes using TMPZnCl·LiCl was written by Balkenhohl, Moritz;Jangra, Harish;Makarov, Ilya S.;Yang, Shu-Mei;Zipse, Hendrik;Knochel, Paul. And the article was included in Angewandte Chemie, International Edition in 2020.SDS of cas: 322-46-3 This article mentions the following:

The development of a predictive model towards site-selective deprotometalation reactions using TMPZnCl·LiCl is reported (TMP = 2,2,6,6-tetramethylpiperidinyl). The pK_a values of functionalized N-, S-, and O-heterocycles, arenes, alkenes, or alkanes were calculated and compared to the exptl. deprotonation sites. Large overlap (>80%) between the calculated and empirical deprotonation sites was observed, showing that thermodn. factors strongly govern the metalation regioselectivity. In the case of olefins, calculated frozen state energies of the deprotonated substrates allowed a more accurate prediction. Addnl., various new N-heterocycles were analyzed and the metalation regioselectivities rationalized using the predictive model. 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. 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.SDS of cas: 322-46-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Hydrophobicity parameter of diazines IV: a new hydrogen-accepting parameter of monosubstituted (di)azines for the relationship of partition coefficients in different solvent systems was written by Yamagami, Chisako;Fujita, Toshio. And the article was included in Journal of Pharmaceutical Sciences in 2000.Name: Ethyl pyrazine-2-carboxylate This article mentions the following:

The authors recently proposed a new H-accepting scale, S_HA, for each member of the substituted (di)azine series from the heat of formation calculated under various dielec. environments by the COSMO method. The S_HA scale was used to examine relations between log P_CL (P_CL: CHCl₃/H₂O partition coefficient) and log P_oct (P_oct: 1-octanol/H₂O partition coefficient) for each of the 2-substituted pyridine (I), monosubstituted pyrazine (II), and pyrimidine (III) series. This S_HA parameter worked nicely, representing the H-accepting effect of the solute mol. A correlation equation with excellent quality, such as log P_CL = a log P_oct + sS_HA + constant, was obtained for each series. The authors further defined the parameter S_HA/PY, derived from S_HA values for the heterocyclic series by shifting the reference points to unsubstituted pyridine, to unify sep. derived correlation equations. Thus, the correlation between log P_CL and log P_oct for all combined data of three series was derived by using a single equation as log P_CL = a log P_oct + sS_HA/PY + constant The S_HA parameters were reasonably considered as being free-energy related, and the rationale for the H-bond-acceptor scale was presented. In the experiment, the researchers used many compounds, for example, Ethyl pyrazine-2-carboxylate (cas: 6924-68-1Name: 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.Name: Ethyl pyrazine-2-carboxylate

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem