54608-52-5

Usage

Uses

Used in Pharmaceutical Industry:
PYRAZIN-2-YL-HYDRAZINE is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
PYRAZIN-2-YL-HYDRAZINE is used as a starting material in the synthesis of various heterocyclic compounds, such as triazolo[4,3-a]pyrazine 7-oxide, 3-β-D-ribofuranosyl-1,2,4-triazolo[4,3-a]pyrazine, monohydrazones of pyridine, and pyrazine. These synthesized compounds have potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.
Used in Organic Synthesis:
PYRAZIN-2-YL-HYDRAZINE is used as a versatile reagent in organic synthesis, allowing for the formation of various functional groups and complex molecular structures. Its ability to participate in a wide range of chemical reactions makes it a valuable tool for the synthesis of novel compounds with potential applications in various industries.

Upstream product

• 14508-49-7 2-chloropyrazin 

Downstream Products

• 58528-48-6 phenyl-pyridin-2-yl-methanone pyrazin-2-ylhydrazone 
• 223743-01-9 C₁₇H₁₄FN₅ 
• 1201943-50-1 3-phenyl-[1,2,4]triazolo[4,3-a]pyrazine 
• 1332301-93-5 3-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyrazine 
• 1202233-20-2 methyl[3-methyl-5-phenyl-1-(pyrazin-2-yl)-1H-pyrazol-4-yl]acetate 
• 717851-32-6 C₁₁H₁₁N₅S 
• 274-82-8 [1,2,4]triazolo[4,3-a]pyrazine 
• 486460-20-2 3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine 
• 205443-43-2 2,6-di-tert-butyl-4-(pyrazin-2-ylhydrazonomethyl)phenol 
• 123518-15-0 3-(5-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazolo<4,3-a>pyrazine 

Relevant academic research and scientific papers

Synthesis and evaluation of the thiosemicarbazone, dithiocarbazonate, and 2'-pyrazinylhydrazone of pyrazinecarboxaldehyde as agents for the treatment of iron overload

Three prototype tridentate ligands (i.e., pyrazinecarboxaldehyde thiosemicarbazone, sodium pyrazinecarboxaldehyde dithiocarbazonate, and pyrazinecarboxalhyde 2'-pyrazinylhydrazone) were prepared and evaluated for their relative abilities to remove iron from model systems designed to mimic particular aspects of chronic transfusional iron overload. These compounds were synthesized by condensation of pyrazinecarboxaldehyde with the appropriate substituted hydrazide. Iron-binding properties were determined, and the ability to remove iron from from the proteins transferrin and ferritin was ascertained. An in vivo model system employing iron-loaded mice was used to demonstrate that all three compounds were effective at reducing tissue iron levels.

Tetrahydroindazole inhibitors of CDK2/cyclin complexes

Over 50 tetrahydroindazoles were synthesized after 7-bromo-3,6,6-trimethyl-1-(pyridin-2-yl)-5,6,7,7a-tetrahydro-1H-indazol-4(3aH)-one (3) was identified as a hit compound in a high throughput screen for inhibition of CDK2 in complex with cyclin A. The activity of the most promising analogues was evaluated by inhibition of CDK2 enzyme complexes with various cyclins. Analogues 53 and 59 showed 3-fold better binding affinity for CDK2 and 2- to 10-fold improved inhibitory activity against CDK2/cyclin A1, E, and O compared to screening hit 3. The data from the enzyme and binding assays indicate that the binding of the analogues to a CDK2/cyclin complex is favored over binding to free CDK2. Computational analysis was used to predict a potential binding site at the CDK2/cyclin E1 interface.

PYRIDINIUM DERIVATIVES AS HERBICIDES

Compounds of the formula (I) (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially as herbicides.

Urea and thiourea derivatives of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1, 2, 4]triazolo[4,3-a]pyrazine: Synthesis, characterization, antimicrobial activity and docking studies

An efficient and robust synthetic procedure was developed primarily for the synthesis of a precursor compound; 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1, 2, 4]triazolo[4,3-a]pyrazine (11), from 2-chloropyrazine (7) through the chemical transformations such as hydrazine substitution, trifluoroacetyl group induction, cyclization and pyrazine ring reduction. A new series of urea derivatives 13a-e and thiourea derivatives 13f-j of compound 11 have been synthesized and the structures of all the compounds were confirmed using spectroscopic analyses such as IR, 1H NMR, 13C NMR, LC-MS and HRMS. The newly synthesized compounds were screened for their in vitro antimicrobial activity against five bacteria and two fungi, in which compounds 13d, 13i and 13j displayed potential activity against bacterial strains and 13a, 13d, 13g and 13j against fungal strains with the MIC values in the range of 6.25–25.0 μg/mL. An overall comparison of the activity results revealed that thiourea derivatives contain better activity than that of urea compounds. Molecular docking studies on poly (ADP-ribose) polymerase 15 (ARTD7, BAL3) demonstrated that all the synthesized compounds possess significant binding energies (-8.1 to -9.8 kcal/mol) with no adverse effect in the active site of protein.

Synthesis, bioactivity, action mode and 3D-QSAR of novel anthranilic diamide derivatives

To study the pesticide effect, action mode, structure-activity relationships (SARs) of anthranilic diamide insecticide and screen highly active pesticides, novel anthranilic diamide derivatives were synthesized. Bioassays indicated that all of the title compounds displayed 100% mortality against diamondback moth and oriental armyworm at 100 mg/L, among which 12v and 12w showed 100% insecticidal acitvity at 5 mg/L. Surprisingly compound 12w exhibited better insecticidal acitvity than commercialized chlorantraniliprole against Pyrausta nubilalis (0.1 mg/L) and Cnaphalocrocis Medinalis (2 mg/L). 3D-QSAR and SARs statistical analysis revealed that title compounds with R2 fixed as methoxy had the highest probability possessing high activity. The calcium fluorescence measurements on neurons revealed that E series compounds containing pyrazinyl may have a molecular target different from caffeine on ryanodine receptors rather than the voltage-gated calcium channel present on cytomembran.

Microwave-Assisted Synthesis and Antituberculosis Screening of Some 4-((3-(Trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-l)methyl)benzenamine Hybrids

In the present investigation, a series of 4-((3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)methyl)benzenamine analogs 6a–o were synthesized and characterized by IR, NMR (1H and 13C), and mass spectra. All newly synthesized compounds 6a–o were prepared under conventional and microwave irradiation methods. These compounds obtained in higher yields and in shorter reaction times in the microwave irradiation method when compared with the conventional method. Synthesized compounds 6a–o were inspected for their in vitro antitubercular activity against Mycobacterium tuberculosis H37Ra using an established XTT reduction menadione assay. Among the screened compounds, 6i (IC50: 1.82?μg/mL), 6j (IC50: 1.02?μg/mL), and 6k (IC50: 1.59?μg/mL) showed excellent activity. Furthermore, compound 6i showed MIC90 value of 16.02?μg/mL. In summary, the results indicate the identification of some novel, selective, and specific inhibitors against M.?tuberculosis that can be explored further for the potential antitubercular drug.

Design, synthesis and biological evaluation of novel 2,4-diaminopyrimidine derivatives as potent antitumor agents

For developing novel therapeutic agents with anticancer activities, two series of novel 2,4-diaminopyrimidine derivatives possessing triazolopiperazine or 1,4,8-triazaspiro[4.5]decan-3-one scaffolds were designed and synthesized. Preliminary investigations showed that some compounds exhibited moderate to excellent potency against four tested cancer cell lines as compared with palbociclib and momelotinib. In particular, the most promising compounds 9k and 13f showed the most potent antitumor activities with IC50 values of 2.14/1.98 μM, 3.59/2.78 μM, 5.52/4.27 μM, and 3.69/4.01 μM against A549, HCT-116, PC-3 and MCF-7 cell lines, respectively. Structure-activity relationship (SAR) studies were conducted based on the variation of the moiety of the aromatic ring and the terminal aniline on the pyrimidine core. Furthermore, the mechanism of their anticancer activity was clarified by further exploring the bioactivity. The results showed that compound 9k obviously inhibited the proliferation of A549 cell lines, induced a great decrease in the mitochondrial membrane potential leading to apoptosis of cancer cells, suppressed the migration of tumor cells and prolonged the A549 cell cycle distribution, representing blockage at the G2-M phase and accumulation at the S phase.

Discovery of Molidustat (BAY 85-3934): A Small-Molecule Oral HIF-Prolyl Hydroxylase (HIF-PH) Inhibitor for the Treatment of Renal Anemia

Small-molecule inhibitors of hypoxia-inducible factor prolyl hydroxylases (HIF-PHs) are currently under clinical development as novel treatment options for chronic kidney disease (CKD) associated anemia. Inhibition of HIF-PH mimics hypoxia and leads to increased erythropoietin (EPO) expression and subsequently increased erythropoiesis. Herein we describe the discovery, synthesis, structure–activity relationship (SAR), and proposed binding mode of novel 2,4-diheteroaryl-1,2-dihydro-3H-pyrazol-3-ones as orally bioavailable HIF-PH inhibitors for the treatment of anemia. High-throughput screening of our corporate compound library identified BAY-908 as a promising hit. The lead optimization program then resulted in the identification of molidustat (BAY 85-3934), a novel small-molecule oral HIF-PH inhibitor. Molidustat is currently being investigated in clinical phase III trials as molidustat sodium for the treatment of anemia in patients with CKD.

Mannich base derivatives of 1,2,4-triazocyclo [4,3-alpha] condensed piperazine as well as preparation method and application of Mannich base derivatives

Mannich base derivatives of 1,2,4-triazocyclo [4,3-alpha] condensed piperazine have the structural formula shown as general formula I in the specification. The Mannich base derivatives have the following advantages: according to a preparation method, substitutive derivatives are prepared from 1,2,4-triazocyclo [4,3-alpha] condensed piperazine by introducing different substituent groups into 1,2,4-triazocyclo [4,3-alpha] condensed piperazine, a novel structure with higher biological activity is discovered, novel structure-activity relationship and biological activity laws are summarized; the prepared Mannich base derivatives have higher bactericidal activity and herbicidal activity, have high in-vitro inhibitory activity for plant pathogens such as fusarium wilt pathogen of cucumbers, cercospora arachidicola, Macrophoma kawatsukai, rhizoctonia cerealis pathogen, alternaria solani of tomatoes, gibberella zeae and the like and can be used for controlling fungus and weed damage to plants, and bactericidal or herbicidal composition further comprises a vector acceptable in agriculture, forestry and hygiene.

Discovery of APD371: Identification of a Highly Potent and Selective CB2 Agonist for the Treatment of Chronic Pain

The discovery of a novel, selective and fully efficacious CB2 agonist with satisfactory pharmacokinetic and pharmaceutical properties is described. Compound 6 was efficacious in a rat model of osteoarthritis pain following oral administration and, in contrast to morphine, maintained its analgesic effect throughout a 5-day subchronic treatment paradigm. These data were consistent with our hypothesis that full agonist efficacy is required for efficient internalization and recycling of the CB2 receptor to avoid tachyphylaxis. Based on its overall favorable preclinical profile, 6 (APD371) was selected for further development for the treatment of pain.