Category: Pyrazines

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Amino-2-fluoropyridine( cas:1827-27-6 ) is researched.Recommanded Product: 5-Amino-2-fluoropyridine.Empel, Anna; Bak, Andrzej; Kozik, Violetta; Latocha, Malgorzata; Cizek, Alois; Jampilek, Josef; Suwinska, Kinga; Sochanik, Aleksander; Zieba, Andrzej published the article 《Towards Property Profiling: SYNTHESIS and SAR Probing of New Tetracyclic Diazaphenothiazine Analogues》 about this compound( cas:1827-27-6 ) in International Journal of Molecular Sciences. Keywords: lung breast cancer SAR anticancer tertiary phenothiazine quinoline; antibacterial activity; antiproliferative activity; azaphenothiazines; lipophilicity; pharmacophore mapping; phenothiazine; similarity-activity landscape index. Let’s learn more about this compound (cas:1827-27-6).

A series of new tertiary phenothiazine derivatives containing a quinoline and a pyridine fragment was synthesized by the reaction of 1-methyl-3-benzoylthio-4-butylthioquinolinium chloride with 3-aminopyridine derivatives bearing various substituents on the pyridine ring. The direction and mechanism of the cyclization reaction of intermediates with the structure of 1-methyl-4-(3-pyridyl)aminoquinolinium-3-thiolate was related to the substituents in the 2- and 4-pyridine position. The structures of the compounds were analyzed using 1H, 13C NMR (COSY, HSQC, HMBC) and X-ray anal., resp. Moreover, the antiproliferative activity against tumor cells (A549, T47D, SNB-19) and a normal cell line (NHDF) was tested. The antibacterial screening of all the compounds was conducted against the reference and quality control strain Staphylococcus aureus ATCC 29213, three clin. isolates of methicillin-resistant S. aureus (MRSA). In silico computation of the intermol. similarity was performed using principal component anal. (PCA) and hierarchical clustering anal. (HCA) on the pool of structure/property-related descriptors calculated for the novel tetracyclic diazaphenothiazine derivatives The distance-oriented property evaluation was correlated with the exptl. anticancer activities and empirical lipophilicity as well. The quant. shape-based comparison was conducted using the CoMSA method in order to indicate the potentially valid steric, electronic and lipophilic properties. Finally, the numerical sampling of similarity-related activity landscape (SALI) provided a subtle picture of the SAR trends.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Agricultural and Biological Chemistry called Asymmetric synthesis of S-carboxymethyl-L-cysteine by a chemicoenzymic method, Author is Yokozeki, Kenzo; Eguchi, Chikahiko; Kamimura, Akira; Kubota, Koji, which mentions a compound: 2150-55-2, SMILESS is O=C(C1N=C(N)SC1)O, Molecular C4H6N2O2S, Reference of 2-Amino-4,5-dihydrothiazole-4-carboxylic acid.

A chemienzymic method is developed for production of S-carboxymethyl-L-cysteine (I) from DL-2-aminothiazoline-4-carboxylic acid (II) in the presence of ClCH2CO2H using a hydrolyzing system. The carboxymethylation of L-cysteine with ClCH2CO2H to I proceeded effectively at 26° and pH ≥8.0, the yield reaching nearly 100%. The carboxymethylation of II with ClCH2CO2H was not observed Next, the production of I from II in the presence of ClCH2CO2H was examined using rinsed cells of Pseudomonas desmolytica AJ-11898. About 10 g I/L was produced from 18 g II/L in 8 h, the molar yield being 45%. This finding shows that the aminothiazolinecarboxylate racemase in P. desmolytica AJ-11898 may be inhibited by the ClCH2CO2H added to the reaction mixture In fact, the II remaining in the reaction mixture was in the D-form. Moreover, the yield of L-cysteine from DL-II in the absence of ClCH2CO2H was ∼50% when cells of AJ-11898 pretreated with SH reagents were used as the enzyme source.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《HDAC4 Inhibitors with Cyclic Linker and Non-hydroxamate Zinc Binding Group: Design, Synthesis, HDAC Screening and in vitro Cytotoxicity evaluation.》. Authors are Tilekar, Kalpana; Hess, Jessica D.; Upadhyay, Neha; Schweipert, Markus; Flath, Felix; Gutierrez, Denisse A.; Loiodice, Fulvio; Lavecchia, Antonio; Meyer-Almes, Franz-Josef; Aguilera, Renato J.; Ramaa, C. S..The article about the compound:5-Amino-2-fluoropyridinecas:1827-27-6,SMILESS:NC1=CN=C(C=C1)F).SDS of cas: 1827-27-6. Through the article, more information about this compound (cas:1827-27-6) is conveyed.

Recent evidences highlight the usefulness of small mol. (Histone deacetylase 4) HDAC4 inhibitors in the several preclin. paradigms. Major toxicity and mutagenicity issues associated with hydroxamate HDAC inhibitors, stimulated us to develop potent non-hydroxamate inhibitors. In the present work a novel series of thiazolidinedione (TZD) derivatives with pyridine as cyclic linker and TZD ring as zinc binding group was designed and screened in a panel of isoenzymes of HDACs, wherein the most potent compounds exhibiting HDAC4 IC50-values<5 μM were 5 v, 5 w, 5 y and 5 z (IC50=4.2±1 μM, 0.75±0.03 μM, 4.9±0.5 and 2.3±0.5 μM, resp.). The docking studies displayed the unique binding mode of this series of compound at active site of HDAC4, wherein TZD ring was indicated as zinc binding group. Further, 5 w and 5 y were found as the most potent antiproliferative agent in lymphoblastic leukemia (CCRF-CEM) and breast cancer MDA-MB-231 cells. Compound 5 y was found to induce the apoptosis and DNA fragmentation of CEM cells. The western blotting anal. of 5 y also showed the presence of cleaved caspases supporting their apoptotic nature. Further, Class IIa (HDAC4) selectivity of 5 y was also supported by western blotting observations, wherein 5 y caused the accumulation of acetylated H3 but not of acetylated Tubulin. Thus, our findings endorse the further investigation of this series of compounds for their potential as targeted cancer therapeutic agents. In addition to the literature in the link below, there is a lot of literature about this compound(5-Amino-2-fluoropyridine)SDS of cas: 1827-27-6, illustrating the importance and wide applicability of this compound(1827-27-6).

Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of C4H5N3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Aminopyrimidine, is researched, Molecular C4H5N3, CAS is 591-54-8, about C-N Coupling of DNA-Conjugated (Hetero)aryl Bromides and Chlorides for DNA-Encoded Chemical Library Synthesis. Author is Chen, Ying-Chu; Faver, John C.; Ku, Angela F.; Miklossy, Gabriella; Riehle, Kevin; Bohren, Kurt M.; Ucisik, Melek N.; Matzuk, Martin M.; Yu, Zhifeng; Simmons, Nicholas.

DNA-encoded chem. library (DECL) screens are a rapid and economical tool to identify chem. starting points for drug discovery. As a robust transformation for drug discovery, palladium-catalyzed C-N coupling is a valuable synthetic method for the construction of DECL chem. matter; however, currently disclosed methods have only been demonstrated on DNA-attached (hetero)aromatic iodide and bromide electrophiles. We developed conditions utilizing an N-heterocyclic carbene-palladium catalyst that extends this reaction to the coupling of DNA-conjugated (hetero)aromatic chlorides with (hetero)aromatic and select aliphatic amine nucleophiles. In addition, we evaluated steric and electronic effects within this catalyst series, carried out a large substrate scope study on two representative (hetero)aryl bromides, and applied this newly developed method within the construction of a 63 million-membered DECL.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: Ethyl oxazole-5-carboxylate, is researched, Molecular C6H7NO3, CAS is 118994-89-1, about Synthetic studies on bengazoles of marine sponge origin. Synthesis of the core bis-oxazole fragments.Reference of Ethyl oxazole-5-carboxylate.

The core bis-oxazole fragment I (R = OCH2OMe, R1 = CHO) was constructed by the coupling of 5-formyloxazole with lithiated 5-(silyoxymethyl)oxazoles, oxidation of the resulting bis(oxazolyl)methanol (II), followed by the asym. reduction with (R)-(+)-BINAL-H as key steps. Addnl., preparation of bis-oxazole fragment I (R = H, R1 = CH2OSiPh2CMe3) was accomplished by the Barton-McCombie radical deoxygenation reaction of II.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Safety of 4-Bromo-1-methyl-2-nitro-1H-imidazole. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Bromo-1-methyl-2-nitro-1H-imidazole, is researched, Molecular C4H4BrN3O2, CAS is 121816-79-3, about Synthesis and reactions of brominated 2-nitroimidazoles. Author is Palmer, Brian D.; Denny, William A..

Imidazoles reacted with N-bromosuccinimide to give 4-bromo derivatives I (R1 = H, Me, CPh3; R2 = H, NO2, Me). 2-Nitroimidazole gave dibromo compound II as the only product. I (R1 = CPh3, R2 = H) was treated with BuLi, PrONO2, and HCl to give I (R1 = H, R2 = NO2).

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Ethyl oxazole-5-carboxylate(SMILESS: O=C(C1=CN=CO1)OCC,cas:118994-89-1) is researched.Safety of 4-Bromo-1-methyl-2-nitro-1H-imidazole. The article 《Visible-Light Photoredox-Catalyzed Decarboxylative Alkylation of Heteroarenes Using Carboxylic Acids with Hydrogen Release》 in relation to this compound, is published in Organic Letters. Let’s take a look at the latest research on this compound (cas:118994-89-1).

Herein, we have developed visible-light photoredox-catalyzed decarboxylating carboxylic acids for alkylation of heteroarenes under mild conditions. The transformation occurred smoothly without the requirement of stoichiometric oxidants in the presence of 0.3 equiv of base, which benefited from the release of hydrogen (H2) and carbon dioxide (CO2). Various substrates and functional groups were tolerated. Primary mechanistic studies suggest that an oxidative quenching pathway and a reductive quenching pathway are both possible in the catalytic cycle.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 2150-55-2, is researched, SMILESS is O=C(C1N=C(N)SC1)O, Molecular C4H6N2O2SJournal, Article, Bioscience, Biotechnology, and Biochemistry called N-carbamoyl-L-cysteine as an intermediate in the bioconversion from D,L-2-amino-Δ2-thiazoline-4-carboxylic acid to L-cysteine by Pseudomonas sp. ON-4a, Author is Tamura, Yoshiharu; Nishino, Mizuka; Ohmachi, Tetsuo; Asada, Yoshihiro, the main research direction is Pseudomonas carbamoylcysteine; 2-amino-Δ 2-thiazoline-4-carboxylic acid (ATC); L-cysteine; N-carbamoyl-L-cysteine (L-NCC); Pseudomonas species; bioconversion.Quality Control of 2-Amino-4,5-dihydrothiazole-4-carboxylic acid.

The authors investigated the conversion of D,L-2-amino-Δ2-thiazoline-4-carboxylic (D,L-ATC) to L-cysteine with Pseudomonas sp. ON-4a, an ATC-assimilating bacterium. Cysteine and N-carbamoylcysteine (NCC), but not S-carbamoylcysteine (SCC), were produced from D,L-ATC by a cell-free extract from the strain. These products were isolated from the reaction mixture and then identified as the L-form. Similar results were obtained with P. putida AJ3865 and unidentified strain TG-3, an ATC-assimilating bacteria. It became clear that L-NCC is an intermediate in the conversion of D,L-ATC to L-cysteine in these Pseudomonas strains. Furthermore, it was suggested that these bacteria have L-ATC hydrolase and L-NCC amidohydrolase.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid(SMILESS: O=C(C1N=C(N)SC1)O,cas:2150-55-2) is researched.Product Details of 2150-55-2. The article 《Development of enzymic process producing L-cysteine. 2. Improvement of Pseudomonas desmolytica for the enzymatic production of L-cystine》 in relation to this compound, is published in Nippon Nogei Kagaku Kaishi. Let’s take a look at the latest research on this compound (cas:2150-55-2).

In a process to produce L-cystine from DL-2-thiazolin-4-carboxylic acid (ATC) using the enzymic activity of Pseudomonas strains, we proposed the oxidation-reduction potential (ORP) as a criterion to optimize the process in the previous paper. To scale up this process, it was required to reduce the generation of hydrogen sulfide (H2S). A mutant strain of P. desmolytica AJ-11071 which has a higher yield of L-cystine from ATC and lower activity of L-cysteine hydrolysis to generate H2S gas was developed in this experiment An improved strain Number4 in a 65 kL reactor produced 90 g /L of L-cystine from 110 g/L ATC at the molar yield of 93% in 36 h.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Ethyl oxazole-5-carboxylate( cas:118994-89-1 ) is researched.Related Products of 118994-89-1.Yang, Ke; Zhang, Cheng; Wang, Peng; Zhang, Yan; Ge, Haibo published the article 《Nickel-catalyzed decarboxylative acylation of heteroarenes by sp2 C-H functionalization》 about this compound( cas:118994-89-1 ) in Chemistry – A European Journal. Keywords: oxoglyoxylic acid oxazole decarboxylative acylation nickel catalyst; oxazole ketone preparation; acylation; decarboxylation; heteroarenes; nickel; sp2 CH bond functionalization. Let’s learn more about this compound (cas:118994-89-1).

Nickel-catalyzed ligand-free decarboxylative cross-coupling of azole derivatives with α-oxoglyoxylic acids was developed. This work represents the first example of decarboxylative cross-coupling reactions, in a C-H bond functionalization manner, through nickel catalysis, and tolerates various functional groups. Addnl., this approach provides an efficient access to (ox)azole ketones, an important structural motif in many medicinal compounds with a broad range of biol. activities. © 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem