Category: Pyrazines

Coats, Steven J. published the artcileParallel methods for the preparation and SAR exploration of N-ethyl-4-[(8-alkyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-aryl-methyl]-benzamides, powerful mu and delta opioid agonists, Recommanded Product: Pyrazin-2-ylboronic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2004), 14(22), 5493-5498, database is CAplus and MEDLINE.

Libraries of azabicyclooctylidenemethylbenzamides such as I are prepared as μ- and δ-opioid agonists using solid-phase and solution-phase methods; qual. relationships between the structures of azabicyclooctylidenebenzamides and their μ- and δ-opioid agonist activities are discussed. 4-(Methoxycarbonyl)benzyl bromide is converted to di-Me 4-(methoxycarbonyl)benzylphosphonate with tri-Me phosphite; base-mediated olefination of N-(ethoxycarbonyl)tropinone, bromination and base treatment, and cleavage of the Et carbamate followed by replacement with an Fmoc moiety yields the intermediate (carboxyphenylbromomethylene)azabicyclooctanecarboxylate II (R = HO; R¹ = Br; R² = Fmoc). Attachment of II (R = HO; R¹ = Br; R² = Fmoc) to a resin-bound ethylamine yields a solid-phase intermediate which undergoes piperidine-mediated deprotection of the Fmoc group, reductive amination with aldehydes, palladium-catalyzed Suzuki coupling with aryl- or heteroarylboronic acids, and trifluoroacetic acid deprotection to yield azabicyclooctylidenemethylbenzamides. Coupling of II (R = HO; R¹ = Br; R² = Fmoc) to ethylamine and deprotection yields intermediate II (R = EtNH; R¹ = Br; R² = H); microwave-mediated reductive amination of II (R = EtNH; R¹ = Br; R² = H) with aldehydes and sodium triacetoxyborohydride, quenching with water, and microwave-mediated Suzuki coupling in the presence of tetrakis(triphenylphosphine)palladium yields azabicyclooctylidenemethylbenzamides. Azabicyclooctylidenemethylbenzamides substituted with a wide variety of aryl groups at the methylene carbon are effective as μ- and δ-opioid agonist. Small substituents at the nitrogen of the azabicyclooctyl ring in azabicyclooctylidenemethylbenzamides are preferred for good μ- and δ-opioid agonist activity; basic and acidic substituents decrease activity (although the effects of basic groups can be mitigated by appropriate aryl substitution at the methylene carbon). I has K_i values of 6.0 nM for the μ-opioid receptor and 3.8 nM for the δ-opioid receptor and is an effective oral antinociceptive agent at a dose of 150 μmol/kg in a 48° mouse hot plate test.

Bioorganic & Medicinal Chemistry Letters published new progress about 762263-64-9. 762263-64-9 belongs to pyrazines, auxiliary class Pyrazine,Boronic acid and ester,Boronic Acids, name is Pyrazin-2-ylboronic acid, and the molecular formula is C4H5BN2O2, Recommanded Product: Pyrazin-2-ylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Kakimoto, Shichiro published the artcileStructure and activity of carbothionamides, Computed Properties of 4604-72-2, the publication is Tuberkulose-Forschungsinstitut Borstel, Jahresbericht (1961), 240-81, database is CAplus.

Approx. 70 carbothionamides were tested for inhibition of growth of Mycobacterium. IR estimation of polarization of the C:S bond showed that increasing negativity correlated with antibacterial activity. Toxicity of compounds was due to H₂S production in acid solution 95 references

Tuberkulose-Forschungsinstitut Borstel, Jahresbericht published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C5H5N3S, Computed Properties of 4604-72-2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Chylewska, Agnieszka published the artcileAttractive S···π and π-π interactions in the pyrazine-2-thiocarboxamide structure: Experimental and computational studies in the context of crystal engineering and microbiological properties, Name: Pyrazine-2-carbothioamide, the publication is Journal of Molecular Structure (2016), 96-104, database is CAplus.

Pyrazine-2-thiocarboxamide (PTCA) was obtained after recrystallization and was characterized by elemental anal., IR spectroscopy and thermogravimetry. Five dimers of PTCA were found in X-ray diffraction studies. These results were then compared with the known structures of a popular drug, i.e. pyrazine-2-carboxamide (PZA). S···π and π-π interactions were observed in the PTCA crystal structure as a novelty in X-ray measurements and our attention was focused on their role in stabilizing the PCTA structure. The geometry, energy and IR spectra for two conformers (E, Z) of PTCA and five dimers (D1-D5) were calculated for the gas phase with the DFT method at 6-311 + G(d,p) basis set. The results of calculations showed that D1 is the most stable dimer among five dimers of PTCA which were found exptl. Thermal decomposition of PTCA was examined with the use of the TG/IR anal. (20-1000 °C) and the results were discussed. To test the antimicrobial activity of PTCA a biol. assay was performed to determine its potentially pharmaceutical applications. The min. inhibitory (MIC) and minimal bactericidal (fungicidal) concentrations (MBC) for PTCA were determined against six microorganisms.

Journal of Molecular Structure published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C5H5N3S, Name: Pyrazine-2-carbothioamide.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Cumming, Jared N. published the artcileStructure based design of iminohydantoin BACE1 inhibitors: Identification of an orally available, centrally active BACE1 inhibitor, Product Details of C4H5BN2O2, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(7), 2444-2449, database is CAplus and MEDLINE.

From an initial lead 2-imino-1-methyl-4,4-diphenyl-5-imidazolidinone, a structure-based design approach led to identification of the novel, high-affinity iminohydantoin BACE1 inhibitor I that lowers CNS-derived Aβ following oral administration to rats. SAR development in the S3 and F’ subsites of BACE1 for this series, the synthetic approaches employed in this effort, and in vivo data for I are reported.

Bioorganic & Medicinal Chemistry Letters published new progress about 762263-64-9. 762263-64-9 belongs to pyrazines, auxiliary class Pyrazine,Boronic acid and ester,Boronic Acids, name is Pyrazin-2-ylboronic acid, and the molecular formula is C4H5BN2O2, Product Details of C4H5BN2O2.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Gampe, Dominique Mario published the artcileMixing Chromophores: Donor-Acceptor Dyes with Low-Lying LUMOs and Narrow Band Gaps by Connecting 4-Alkoxythiazoles and Azaacenes, Related Products of pyrazines, the publication is European Journal of Organic Chemistry (2017), 2017(10), 1369-1379, database is CAplus.

The synthesis and characterization of novel donor-acceptor (D-A) type functional dyes is presented. The materials studied are based on the 4-alkoxythiazole structure containing one of three arylamine donor units and one of three acceptor building blocks. The nine dyes were characterized with respect to their photo- and electrochem. properties based on UV/Vis absorption and fluorescence emission spectroscopy, and cyclic voltammetry. D. functional theory calculations were carried out to support these studies. The building blocks used brought their characteristics into the final target structures: the reversible oxidation and electron-donating properties of diarylamines, the high fluorescence quantum yields of 4-alkoxythiazoles, and the low-lying LUMOs of tetraazaanthracenes. Furthermore, by introducing tetraazaanthracenes as the acceptor moiety, narrow band gaps of 1.1 and 0.7 eV were estimated electrochem.

European Journal of Organic Chemistry published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C5H5N3S, Related Products of pyrazines.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Wang, Changliu published the artcileYnamide-Mediated Thioamide and Primary Thioamide Syntheses, Name: Pyrazine-2-carbothioamide, the publication is Journal of Organic Chemistry (2022), 87(9), 5617-5629, database is CAplus and MEDLINE.

Environmentally friendly ynamide-mediated thioamidation of monothiocarboxylic acids with amines or ammonium hydroxide for the synthesis of thioamides was described. Simple and mild reaction conditions tolerate a wide variety of functional groups such as hydroxyl, ester, tertiary amine, ketone, and amide moieties. Readily available NaSH served as the sulfur source, avoiding the use of toxic, expensive, and malodorous organic sulfur reagents and making this strategy environmentally friendly and practical. Importantly, the stereochem. integrity of α-chiral monothiocarboxylic acids was maintained during the activation step and subsequent aminolysis process, which offers a racemization-free strategy for peptide and protein C-terminal modification. Furthermore, a number of thioamide-modified drugs were prepared in good yields by this protocol and the synthesized primary thioamides were transformed into backbone thiazolyl modification peptides.

Journal of Organic Chemistry published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C6H8O3, Name: Pyrazine-2-carbothioamide.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Rada, B. published the artcileInhibition of virus multiplication by some derivatives of pyridine- and pyrazinecarboxylic acid, Recommanded Product: Pyrazine-2-carbothioamide, the publication is Acta Virologica (English Edition) (1971), 15(4), 326-8, database is CAplus and MEDLINE.

In agar-diffusion plaque-inhibition test with 25 derivatives of pyridine- and pyrazinemono-carboxylic acid, 2-bromo-4-thiocarbamoylpyridine (I) was found effective against vaccinia virus, forming an inhibition zone of medium size without any toxic effect, while 2,6-diethoxy-4-hydroxycarbamoylpyridine and 2-butoxy-4-hydroxycarbamoylpyridine formed large zones of inhibition against vaccinia and western equine encephalomyelitis viruses together with smaller toxic zones.

Acta Virologica (English Edition) published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C5H5N3S, Recommanded Product: Pyrazine-2-carbothioamide.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Lumma, William C. Jr. published the artcilePiperazinylpyrazines with central serotoninmimetic activity, Application of 2-Chloro-6-(trifluoromethyl)pyrazine, the publication is Journal of Medicinal Chemistry (1978), 21(6), 536-42, database is CAplus and MEDLINE.

Twenty title compounds I [R = H, [CH₂)₃NMe₂, or 6-chloro-2-pyrazinyl; R = H or Cl; R² = H, Cl, Ph, or CO₂Me; R³ = H, Cl, Me, SPh, etc.; X = 2H or O] were synthesized by reaction of the appropriate chloropyrazine with piperazine [110-85-0] or an N-substituted piperazine. I; (R = R¹ = R² = H; R³ = Cl; X = 2H,.HCl) [61655-58-1] had pharmacol. properties in mice characteristic of potent central serotoninmimetic activity and only weak peripheral serotoninmimetic action in isolated rat uterus. Preferred conformations of this compound, determined by classical strain energy calculations and CNDO mol. orbital techniques, were compared with serotonin [50-67-9] in order to determination those structural features which might interact with serotonin receptors.

Journal of Medicinal Chemistry published new progress about 61655-69-4. 61655-69-4 belongs to pyrazines, auxiliary class Trifluoromethyl,Pyrazine,Fluoride,Chloride, name is 2-Chloro-6-(trifluoromethyl)pyrazine, and the molecular formula is C5H2ClF3N2, Application of 2-Chloro-6-(trifluoromethyl)pyrazine.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Adamova, Katerina published the artcileAntifungal action of acylated thioamides and related compounds, Name: Pyrazine-2-carbothioamide, the publication is Acta Universitatis Palackianae Olomucensis, Facultas Rerum Naturalium (1991), 102(Chem. 30), 155-60, database is CAplus.

Some acylated thioamides and similar compounds were tested for their antifungal properties. Only 3 thioamides, thiophthalic anhydride, and some thiuram disulfides had good activity. The condensation of thioamides with Me isothiocyanate gave active compounds The activity of thiuram disulfides was related to the solubility in water.

Acta Universitatis Palackianae Olomucensis, Facultas Rerum Naturalium published new progress about 4604-72-2. 4604-72-2 belongs to pyrazines, auxiliary class Pyrazine,Amine,Amide, name is Pyrazine-2-carbothioamide, and the molecular formula is C5H5N3S, Name: Pyrazine-2-carbothioamide.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem

Warner, Katherine Deigan published the artcileValidating Fragment-Based Drug Discovery for Biological RNAs: Lead Fragments Bind and Remodel the TPP Riboswitch Specifically, Related Products of pyrazines, the publication is Chemistry & Biology (Oxford, United Kingdom) (2014), 21(5), 591-595, database is CAplus and MEDLINE.

Thiamine pyrophosphate (TPP) riboswitches regulate essential genes in bacteria by changing conformation upon binding intracellular TPP. Previous studies using fragment-based approaches identified small mol. “fragments” that bind this gene-regulatory mRNA domain. Crystallog. studies now show that, despite having micromolar K_ds, four different fragments bind the TPP riboswitch site-specifically, occupying the pocket that recognizes the aminopyrimidine of TPP. Unexpectedly, the unoccupied site that would recognize the pyrophosphate of TPP rearranges into a structure distinct from that of the cognate complex. This idiosyncratic fragment-induced conformation, also characterized by small-angle X-ray scattering and chem. probing, represents a possible mechanism for adventitious ligand discrimination by the riboswitch, and suggests that off-pathway conformations of RNAs can be targeted for drug development. Our structures, together with previous screening studies, demonstrate the feasibility of fragment-based drug discovery against RNA targets.

Chemistry & Biology (Oxford, United Kingdom) published new progress about 59944-75-1. 59944-75-1 belongs to pyrazines, auxiliary class Other Aromatic Heterocyclic,Amine, name is Thieno[2,3-b]pyrazin-7-amine, and the molecular formula is C17H14F3N3O2S, Related Products of pyrazines.

Referemce:
https://en.wikipedia.org/wiki/Pyrazine,
Pyrazine | C4H4N2 – PubChem