Category: Pyrazines

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Zwitterion structure and acylative ring-opening reactions of 2-aminothiazoline-4-carboxylic acid》. Authors are Gawron, Oscar; Fernando, Joseph; Keil, John; Weismann, T. J..The article about the compound:2-Amino-4,5-dihydrothiazole-4-carboxylic acidcas:2150-55-2,SMILESS:O=C(C1N=C(N)SC1)O).Related Products of 2150-55-2. Through the article, more information about this compound (cas:2150-55-2) is conveyed.

pKA values (pK1 2.03, pK2 8.48), variation of optical rotation with pH and other phys. properties indicate that 2-aminothiazoline-4-carboxylic acid is a zwitterion in solution and in the solid state anti that pK2 can be ascribed to ionization from the ring nitrogen. Acylation of 2-aminothiazoline-4-carboxylic acid in aqueous medium is accompanied by ring opening. With Ac2O N’, S-diacetyl-N-carbamoylcysteine is obtained and with BzCl S-benzoyl-N-carbamylcysteine and 2-imino-3-benzoylthiazolidine-4-carboxylic acid are obtained. Structures of the acylated products were proven by chem. methods and by interpretation of nuclear magnetic resonance data

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid, is researched, Molecular C4H6N2O2S, CAS is 2150-55-2, about Study on L-cystine conversion technology by Pseudomonas putida TS1138, the main research direction is Pseudomonas cystine cysteine.Quality Control of 2-Amino-4,5-dihydrothiazole-4-carboxylic acid.

A technol. of L-cystine production was studied in this paper, which included microbial enzymic conversion of DL-2-amino-Δ2-thiazoline-4- carboxylic acid (DL-ATC) to L-cysteine, subsequent oxidization of L-cysteine to L-cystine and its purification The cells of Pseudomonas putida TS1138 could be repetitively used as the enzyme sources to convert the substrate DL-ATC to L-cysteine. After being oxidized by 2% dimethy-sulfoxide (DMSO), L-cystine could be harvested and further purified by the pos. ion-exchange resin 001*7. High Performance Liquid Chromatog. (HPLC) identified the purified L-cystine as having a total recovery of 78.55% and purity of 99.12%. This study demonstrated an efficient and convenient method for L- cystine production, which overcame the instability of enzymes, troublesome procedures and high cost of enzyme immobilization as contrasted to the traditional method. All in all, it provides a new approach for industrial production of L- cystine as well as L-cysteine.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Recommanded Product: 4-Aminopyrimidine. 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 Design, synthesis, molecular docking and cytotoxic activity of novel urea derivatives of 2-amino-3-carbomethoxythiophene. Author is Vikram, Venugopalarao; Penumutchu, Srinivasa R.; Vankayala, Raviraj; Thangudu, Suresh; Amperayani, Karteek Rao; Parimi, Umadevi.

An efficient feasible route for the one-pot synthesis of novel series of urea derivatives (2a-2j) from 2-amino-3-carbomethoxythiophene (1) via in situ isocyanate has been developed, and their corresponding anticancer activities were accomplished. The series of urea derivatives were characterized by using 1H, 13C NMR and mass spectroscopic anal. The cytotoxic activities were evaluated against human cervical (HeLa) and human lung (NCI-H23) cancer cell lines. These studies revealed satisfactory activity for some of the compounds, which could potentially serve as lead compounds for drug discovery and development. Furthermore, mol. docking studies supported in identifying the potential binding sites between the urea derivatives and eukaryotic ribonucleotidereductase (RR). High ambiguity driven docking (HADDOCK) modeling was specifically employed to determine the model complex of RR and urea derivatives The proposed model has provided a deep insight into the mol. level interactions of RR-urea model complexes in understanding the exact pharmacophore for designing highly potent RR inhibitors. Overall, the present work has shed light in developing a feasible and robust approach for the synthesis of novel urea derivatives of 2-amino-3-carbomethoxythiophene and identified a part of mol. structure that is responsible for a specific biol. interaction leading to potential anticancer activities. Graphic abstract: We report herein, the exptl. design, synthesis and characterization of a novel series of urea derivatives of 2-amino-3carbomethoxythiophene with pyrimidine amine and benzyl amine analogs as both derivatives which exhibited potential antitumor activity via one pot synthesis and subsequently studied the structure activity relationships (SAR), and anticancer activities. The docking studies identified a part of molecularstructure that is responsible for a specific biol. interaction leading to the destruction of cancer cells.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 2150-55-2, is researched, Molecular C4H6N2O2S, about Optimization of bioconversion conditions for manufacturing L-cysteine from DL-2-amino-Δ2-thiazoline-4-carboxylic acid with immobilized cells based on response surface analysis, the main research direction is cysteine immobilization Pseudomonas.Application In Synthesis of 2-Amino-4,5-dihydrothiazole-4-carboxylic acid.

The conversion conditions for manufacturing L-cysteine using immobilized cells were optimized by using SAS software combined with the methods of Plackett-Burman design and response surface methodol. The cells were immobilized by calcium alginate embedding method. The optimum levels of three important factors were determined as follows: the volume of immobilized cell was 25.5 mL, the concentration of DL-2-amino-Δ2-thiazoline-4-carboxylic acid (DL-ATC) was 1.0 mass%, and the proliferation time of immobilized cells was 12.9 h. Experiments showed that the average enzyme activity could reach 934 U/mL at optimized conditions for five batches, with an increase of 38.9% compared with that before the optimization. After the immobilized cells were utilized for 4 times, the conversion rate could be still over 91.0% of the initial value.

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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.Formula: C6H7NO3.Webb, Michael R.; Addie, Matthew S.; Crawforth, Catherine M.; Dale, James W.; Franci, Xavier; Pizzonero, Mathieu; Donald, Craig; Taylor, Richard J. K. published the article 《The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach》 about this compound( cas:118994-89-1 ) in Tetrahedron. Keywords: asym synthesis inthomycin B C Mukaiyama aldol reaction; Stille coupling reaction asym synthesis inthomycin A B C. Let’s learn more about this compound (cas:118994-89-1).

The Stille coupling between a common oxazole vinyl iodide and stereodefined stannyl-diene units is described as the cornerstone of a unified synthetic route to the inthomycin family of bioactive Streptomyces metabolites. This procedure has been utilized to prepare (+)-inthomycin B (I) and (+)-inthomycin C (II) for the first time; in these examples the stereogenic center was introduced using the Kiyooka ketene acetal/amino acid-derived oxazaborolidinone variant of the Mukaiyama aldol reaction. In addition, a convenient preparation of rac-inthomycin A (III) is described based on the same strategy.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

HPLC of Formula: 2150-55-2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid, is researched, Molecular C4H6N2O2S, CAS is 2150-55-2, about Theoretical and experimental approach to hydrophilic interaction dispersive solid-phase extraction of 2-aminothiazoline-4-carboxylic acid from human post-mortem blood. Author is Giebultowicz, Joanna; Sobiech, Monika; Ruzycka, Monika; Lulinski, Piotr.

The authors proposed an innovative hydrophilic interaction dispersive solid-phase extraction (HI-d-SPE) protocol suitable for the isolation of the potential cyanide intoxication marker, 2-aminothiazoline-4-carboxylic acid (ATCA), from such complicated matrix as post-mortem blood. To create an optimal HI-d-SPE protocol, two sorbents were used: a molecularly imprinted polymer (MIP) and com. available Oasis-MCX. The latter sorbent was identified as more recovery-efficient with higher clean-up abilities in a carefully optimized process. Computational anal. was employed to provide insight into the adsorption mechanism of the two selected sorbents. The theor. results were in agreement with the experiment regarding the efficiency of the sorbent. HI-d-SPE was successfully applied to the anal. of ATCA in 20 post-mortem blood samples using LC-MS/MS. The anal. performance of the method was finally compared to prior existing methods, in turn revealing its superiority.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Recommanded Product: Ethyl oxazole-5-carboxylate. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Ethyl oxazole-5-carboxylate, is researched, Molecular C6H7NO3, CAS is 118994-89-1, about Direct C2-Heteroarylation of Indoles by Rhodium-Catalyzed C-C Bond Cleavage of Secondary Alcohols. Author is Yu, Tian-Yang; Zheng, Zhao-Jing; Sun, Wei; Qiao, Zi-Heng.

A rhodium-catalyzed direct heteroarylation of indoles by cleavage of an inert C-C bond of alcs. is reported. This catalytic system exhibits high reactivity and tolerates various functional groups. This reaction provides a tool for the rapid construction of biheteroaryls without pre-activation of the starting materials. Control experiments were conducted to determine a possible mechanism. This reaction makes a significant contribution to the field of C-C bond activation of alcs.

After consulting a lot of data, we found that this compound(118994-89-1)Recommanded Product: Ethyl oxazole-5-carboxylate can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Chittari, Pabba; Hamada, Yasumasa; Shioiri, Takayuki researched the compound: Ethyl oxazole-5-carboxylate( cas:118994-89-1 ).Safety of Ethyl oxazole-5-carboxylate.They published the article 《Synthetic studies on bengazoles of marine sponge origin. Synthesis of the core bis-oxazole fragments》 about this compound( cas:118994-89-1 ) in Synlett. Keywords: bisoxazole bengazole core preparation; oxazole bengazole core preparation. We’ll tell you more about this compound (cas:118994-89-1).

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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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 2150-55-2. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid, is researched, Molecular C4H6N2O2S, CAS is 2150-55-2, about Cysteine. Author is Nagasawa, Toru; Yamada, Hideaki.

A review with 21 references on the microbial conversion of DL-2-amino-Δ2-thiazoline-4-carboxylic acid  [2150-55-2] to L-cysteine  [52-90-4] and cystine  [56-89-3]; the enzymic synthesis of L-cysteine from β-chloro-L-alanine  [2731-73-9] and Na2S by pyridoxal phosphate-dependent enzymes; and the synthesis of D-cysteine  [921-01-7] by β-chloro-D-alanine dehydrochlorinase  [78990-65-5].

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1827-27-6. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5-Amino-2-fluoropyridine, is researched, Molecular C5H5FN2, CAS is 1827-27-6, about 5-Azido-2-aminopyridine, a New Nitrene/Nitrenium Ion Photoaffinity Labeling Agent That Exhibits Reversible Intersystem Crossing between Singlet and Triplet Nitrenes. Author is Panov, Maxim S.; Voskresenska, Valentyna D.; Ryazantsev, Mikhail N.; Tarnovsky, Alexander N.; Wilson, R. Marshall.

The photochem. of a new photoaffinity labeling (PAL) agent, 5-azido-2-(N,N-diethylamino)-pyridine, was studied in aprotic and protic solvents using femtosecond-to-microsecond transient absorption and product anal., in conjunction with ab initio multiconfigurational and multireference quantum chem. calculations The excited singlet S1 state is spectroscopically dark, whereas photoexcitation to higher-lying singlet excited S2 and S3 states drives the photochem. reaction toward a barrierless ultrafast relaxation path via two conical intersections to S1, where N2 elimination leads to the formation of the closed-shell singlet nitrene. The singlet nitrene undergoes intersystem crossing (ISC) to the triplet nitrene in aprotic and protic solvents as well as protonation to form the nitrenium ion. The ISC rate constants in aprotic solvents increase with solvent polarity, displaying a “”direct”” gap effect, whereas an “”inverse”” gap effect is observed in protic solvents. Transient absorption actinometry experiments suggest that a solvent-dependent fraction from 20% to 50% of nitrenium ions is generated on a time scale of a few tens of picoseconds. The closed-shell singlet and triplet nitrene are separated by a small energy gap in protic solvents. As a result, the unreactive triplet state nitrene undergoes delayed, thermally activated reverse ISC to reform the reactive closed-shell singlet nitrene, which subsequently protonates, forming the remaining fraction of nitrenium ions. The product studies demonstrate that the resulting nitrenium ion stabilized by the electron-donating 4-amino group yields the final cross-linked product with high, almost quant. efficiency. The enhanced PAL function of this new azide with respect to the widely applied 4-amino-3-nitrophenyl azide is discussed.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem