Month: April 2022

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

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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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: 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

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《4,6-Dichloro- and 4,5,6-trichloropicolinic acid》. Authors are Graf, Roderich.The article about the compound:3-Chloropicolinamidecas:114080-95-4,SMILESS:O=C(N)C1=NC=CC=C1Cl).Quality Control of 3-Chloropicolinamide. Through the article, more information about this compound (cas:114080-95-4) is conveyed.

cf. C. A. 25, 2428. Picolinic acid-HCl (200 g.) and 350 cc. SOCl2, gently boiled 10 days, give 30 g. mono-Cl acid, 100 g. di-Cl acid and 30 g. of a mixture of the di- and tri-Cl acids. That the di-Cl acid is the 4,6-Cl2 derivative is shown by the following reactions: The acid chloride and N2H4.H2O in C6H6 give sec-bis(4,6-dichloropicolinic acid) hydrazide, m. above 300°; the Me ester gives 4,6-dichloropicolinic acid hydrazide, m. 154° (benzal derivative, m. 165°); the azide m. 74° and with absolute EtOH yields 4,6-di-chloro-2-carbethoxypyridine, m. 75°; dilute AcOH gives the 2-NH2 derivative (I), m. 108°; with HI I yields a compound, m. 137°, which may be the 6-iodo-4-chloro derivative The Ac derivative of I n. 218-9°. The diazo solution from I in H2SO4 gives 4,6-dichloro-2-hydroxy-pyridine, m. 151°, and in concentrated HCl gives 2,4,6-trichloropyridine, m. 33°; this also results from 2,6-dichloro-4-aminopyridine. Heating the 4,6-Cl2 acid with 80% H2SO4 8 hrs. gives 4-chloro-6-hydroxypicolinic acid (Seyfferth, J. Chem. Soc. 67, 408(1895). 4,5,6-Trichloropicolinic acid (II), crystallizing with 1 mol. H2O, m. 123°, is obtained pure by distillation of the chloride and then of the Me ester, m. 125°; II and HI with some red P, heated 8 hrs. at 150°, give 5-chloropicolinic acid, m. 170°. The amide of II m. 169°; the Ph ester m. 138°. Heating the Me ester with HI and red P 5 hrs. gives 4-iodo-5-chloropicolinic acid, m. 159° (decomposition); refluxed with SOCl2 for 4 hrs., the I is replaced by Cl, giving 4,5-dichloropicolinic acid, crystals with 1 mol. H2O, m. 179-80° (Ost, J. prakt. Chem. 27, 274(1882)). Refluxing the Me ester with 80% H2SO4 4 hrs. gives 4,5-dichloro-6-hydroxypicolinic acid, crystallizing with 1 mol. H2O, m. 284° (decomposition). 3-Chloropicolinic acid, m. 121°; amide, m. 140°.

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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 Theoretical and experimental approach to hydrophilic interaction dispersive solid-phase extraction of 2-aminothiazoline-4-carboxylic acid from human post-mortem blood, the main research direction is hydrophilic interaction dispersive solid phase extraction; 2-Aminothiazoline-4-carboxylic acid; Dispersive solid phase extraction; Human post-mortem blood; Mixed-mode cation exchange sorbent; Molecular modeling; Molecularly imprinted polymer.Related Products of 2150-55-2.

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

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 4-Aminopyrimidine(SMILESS: C1=CN=CN=C1N,cas:591-54-8) is researched.Electric Literature of C6H7NO3. The article 《Synthesis of Dipeptide, Amide, and Ester without Racemization by Oxalyl Chloride and Catalytic Triphenylphosphine Oxide》 in relation to this compound, is published in Organic Letters. Let’s take a look at the latest research on this compound (cas:591-54-8).

An efficient triphenylphosphine oxide-catalyzed amidation and esterification for the rapid synthesis of a series of dipeptides ((2S,2S)/(2S,2R))-RNHCH(R1)C(O)N(R2)CH(C(O)OR3)R4 [R = (tert-butoxy)carbonyl, (9H-fluoren-9-ylmethoxy)carbonyl, (benzyloxy)carbonyl; R1 = Me, Bn, [(acetamidomethyl)sulfanyl]methyl, (tert-butoxy)methyl, etc.; R2 = H; R3 = Me, t-Bu; R4 = 2-methylpropyl, propan-2-yl, Bn; R2R4 = -(CH2)3-], amides (S)-R5N(R6)C(O)C(R7)(CH3)C6H5 (R5 = 2-methylpropyl, 3,4-dicyanophenyl, pyridin-4-yl, 1-(tert-butoxy)-1-oxo-3-phenylpropan-2-yl, etc.; R6 = H; R5R6 = -(CH2)2N(Boc)(CH2)2-; R7 = H, Me) and esters (S)-(Fmoc)NHCH(R1)C(O)OR8 (R1 = Me, Bn; R8 = Me, Ph, cyclohexyl, etc.) is described. This reaction is applicable to challenging couplings of hindered carboxylic acids (S)-RNHCH(R1)C(O)OH, C6H5C(CH3)(R7)C(O)OH, and (S)-(Fmoc)NHCH(R1)C(O)OH with weakly nucleophilic amines ((S)/(R))-NH(R2)CH(C(O)OR3)R4, R5NH(R6) or alcs., R8OH giving the products in good yields (67-90%) without racemization. This system employs the highly reactive intermediate Ph3PCl2 as the activator of the carboxylate in a catalytic manner and drives the reaction to completion in a short reaction time (less than 10 min).

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of C6H7NO3. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Ethyl oxazole-5-carboxylate, is researched, Molecular C6H7NO3, CAS is 118994-89-1, about Construction of 2-(2-Arylphenyl)azoles via Cobalt-Catalyzed C-H/C-H Cross-Coupling Reactions and Evaluation of Their Antifungal Activity. Author is Wang, Xinmou; Chen, Yuming; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin.

Although compounds with a 2-(2-arylphenyl) benzoxazole motif are biol. important, there are only a few methods for synthesizing them. Herein, authors report an efficient method for synthesis of such compounds by means of cobalt-catalyzed C-H/C-H cross-coupling reactions. This method has a broad substrate scope and good tolerance for sensitive functional groups. In addition, authors demonstrate that introducing a heteroarene moiety to biphenyl compounds enhanced their antifungal activity.

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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.Youn, Sung Hun; Park, Hae Woong; Choe, Deokyeong; Shin, Chul Soo researched the compound: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid( cas:2150-55-2 ).Reference of 2-Amino-4,5-dihydrothiazole-4-carboxylic acid.They published the article 《Preparation of eutectic substrate mixtures for enzymatic conversion of ATC to L-cysteine at high concentration levels》 about this compound( cas:2150-55-2 ) in Bioprocess and Biosystems Engineering. Keywords: enzymic conversion eutectic mixture cysteine production. We’ll tell you more about this compound (cas:2150-55-2).

High concentration eutectic substrate solutions for the enzymic production of L-cysteine were prepared Eutectic melting of binary mixtures consisting of D,L-2-amino-Δ2-thiazoline-4-carboxylic acid (ATC) as a substrate and malonic acid occurred at 39 °C with an ATC mole fraction of 0.5. Formation of eutectic mixtures was confirmed using SEM, SEM-EDS, and XPS surface analyses. Sorbitol, MnSO4, and NaOH were used as supplements for the enzymic reactions. Strategies for sequential addition of five compounds, including a binary ATC mixture and supplements, during preparation of eutectic substrate solutions were established. Eutectic substrate solutions were stable for 24 h. After 6 h of enzymic reactions, a 550 mM L-cysteine yield was obtained from a 670 mM eutectic ATC solution

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Munoz, Juan de M.; Alcazar, Jesus; de la Hoz, Antonio; Diaz-Ortiz, Angel published an article about the compound: Ethyl oxazole-5-carboxylate( cas:118994-89-1,SMILESS:O=C(C1=CN=CO1)OCC ).Recommanded Product: Ethyl oxazole-5-carboxylate. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:118994-89-1) through the article.

The reduction of esters to aldehydes is an important transformation in organic chem. and several reducing agents have been described. However, the use of this reaction in medicinal and natural product chem. is limited due to the instability of the intermediates and the high reactivity of the reaction products. In the current article, the general and selective reduction of esters with lithium diisobutyl-tert-butoxyaluminum hydride (LDBBA) in flow is reported. This reagent allows esters to be reduced in the presence of different functional groups, including those considered to be of similar or higher reactivity.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Seizures and selective CA-1 hippocampal lesions induced by an excitotoxic cyanide metabolite, 2-iminothiazolidine-4-carboxylic acid, published in 1995, which mentions a compound: 2150-55-2, Name is 2-Amino-4,5-dihydrothiazole-4-carboxylic acid, Molecular C4H6N2O2S, HPLC of Formula: 2150-55-2.

Excitatory amino acid (EAA)-like and excitotoxic properties of the secondary metabolite of cyanide, 2-iminothiazolidine-4-carboxylic acid (2-ICA), were evaluated because of its possible role in cyanide-induced neurotoxicity. Intracerebroventricular (i.c.v.) injections of 2-ICA in mice produced wild-running seizures that were qual. and quant. similar to seizures observed with glutamate. 2-ICA, kainate, and proline seizures were prevented by both the NMDA and non-NMDA antagonists, MK-801 and CNQX, resp. In contrast, NMDA-induced seizures were prevented by MK-801, but not CNQX. When infused i.c.v. in rats over a 7-day period, 2-ICA produced extensive and selective loss of CA-1 pyramidal neurons of the hippocampus. In hippocampal slices preloaded with D-[3H]aspartate, 2-ICA superfusion did not evoke release nor significantly augment potassium-stimulated release of the radiolabeled transmitter. These findings indicate 2-ICA has excitotoxic properties and its role in cyanide neurotoxicity deserves further study.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem