Category: 1827-27-6

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.Empel, Anna; Bak, Andrzej; Kozik, Violetta; Latocha, Malgorzata; Cizek, Alois; Jampilek, Josef; Suwinska, Kinga; Sochanik, Aleksander; Zieba, Andrzej researched the compound: 5-Amino-2-fluoropyridine( cas:1827-27-6 ).Safety of 5-Amino-2-fluoropyridine.They 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. We’ll tell you 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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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 《Aromatic fluorine compounds. X. The 2,3- and 2,6-difluoropyridines》. Authors are Finger, G. C.; Starr, Laurence D.; Roe, Arthur; Link, William J..The article about the compound:5-Amino-2-fluoropyridinecas:1827-27-6,SMILESS:NC1=CN=C(C=C1)F).Application of 1827-27-6. Through the article, more information about this compound (cas:1827-27-6) is conveyed.

cf. CA 54, 6713i. The preparation of difluoropyridines by the Schiemann reaction was investigated. 2-Amino-6-fluoropyridine, necessary for the synthesis of 2,6-difluoropyridine by the Schiemann reaction, was conveniently prepared by the Curtius degradation of 6-fluoropicolinic hydrazide and by the Hofmann reaction on 6-fluoropicolinamide. Since an α-fluorine on a pyridine nucleus is preferentially replaced by hydrazine when it is either adjacent to or opposite a carbomethoxy group, the hydrazides necessary for the synthesis of 3-amino-2- and 6-fluoropyridine could not be prepared These amines were prepared from the appropriate 2-fluoropyridinecarboxamide by the Hofmann reaction. The preparation of difluoropyridines was successful with two of the aminofluoropyridines and led to the following new compounds: 2,3-difluoro- and 2,6-difluoropyridine.

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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 5-Azido-2-aminopyridine, a New Nitrene/Nitrenium Ion Photoaffinity Labeling Agent That Exhibits Reversible Intersystem Crossing between Singlet and Triplet Nitrenes, published in 2013-12-26, which mentions a compound: 1827-27-6, Name is 5-Amino-2-fluoropyridine, Molecular C5H5FN2, Product Details of 1827-27-6.

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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Synthetic Route of C5H5FN2. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 5-Amino-2-fluoropyridine, is researched, Molecular C5H5FN2, CAS is 1827-27-6, about Soluble-type small-molecule CD4 mimics as HIV entry inhibitors. Author is Kobayakawa, Takuya; Konno, Kiju; Ohashi, Nami; Takahashi, Kohei; Masuda, Ami; Yoshimura, Kazuhisa; Harada, Shigeyoshi; Tamamura, Hirokazu.

Several small mol. CD4 mimics have been reported previously as HIV-1 entry inhibitors, which block the interaction between the Phe43 cavity of HIV-1 gp120 and the host CD4. Known CD4 mimics such as NBD-556 possess significant anti-HIV activity but are less soluble in water, perhaps due to their hydrophobic aromatic ring-containing structures. Compounds with a pyridinyl group in place of the Ph group in these mols. have been designed and synthesized in an attempt to increase the hydrophilicity. Some of these new CD4 mimics, containing a tetramethylpiperidine ring show significantly higher water solubility than NBD-556 and have high anti-HIV activity and synergistic anti-HIV activity with a neutralizing antibody. The CD4 mimic that has a cyclohexylpiperidine ring and a 6-fluoropyridin-3-yl ring has high anti-HIV activity and no significant cytotoxicity. The present results will be useful in the future design and development of novel soluble-type mol. CD4 mimics.

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Synthetic Route of C5H5FN2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Amino-2-fluoropyridine, is researched, Molecular C5H5FN2, CAS is 1827-27-6, about Amide-containing α-hydroxytropolones as inhibitors of hepatitis B virus replication. Author is Li, Qilan; Lomonosova, Elena; Donlin, Maureen J.; Cao, Feng; O’Dea, Austin; Milleson, Brienna; Berkowitz, Alex J.; Baucom, John-Charles; Stasiak, John P.; Schiavone, Daniel V.; Abdelmessih, Rudolf G.; Lyubimova, Anastasiya; Fraboni, Americo J.; Bejcek, Lauren P.; Villa, Juan A.; Gallicchio, Emilio; Murelli, Ryan P.; Tavis, John E..

The Hepatitis B Virus (HBV) RNase H (RNaseH) is a promising but unexploited drug target. Here, we synthesized and analyzed a library of 57 amide-containing α-hydroxytropolones (αHTs) as potential leads for HBV drug development. Fifty percent effective concentrations ranged from 0.31 to 54μM, with selectivity indexes in cell culture of up to 80. Activity against the HBV RNaseH was confirmed in semi-quant. enzymic assays with recombinant HBV RNaseH. The compounds were overall poorly active against human RNase H1, with 50% inhibitory concentrations of 5.1 to >1,000μM. The aHTs had modest activity against growth of the fungal pathogen Cryptococcus neoformans, but had very limited activity against growth of the Gram – bacterium Escherichia coli and the Gram + bacterium Staphylococcus aureus, indicating substantial selectivity for HBV. A mol. model of the HBV RNaseH templated against the Ty3 RNaseH was generated. Docking the compounds to the RNaseH revealed the anticipated binding pose with the divalent cation coordinating motif on the compounds chelating the two Mn++ ions modeled into the active site. These studies reveal that that amide aHTs can be strong, specific HBV inhibitors that merit further assessment toward becoming anti-HBV drugs.

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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.SDS of cas: 1827-27-6.Li, Qilan; Lomonosova, Elena; Donlin, Maureen J.; Cao, Feng; O’Dea, Austin; Milleson, Brienna; Berkowitz, Alex J.; Baucom, John-Charles; Stasiak, John P.; Schiavone, Daniel V.; Abdelmessih, Rudolf G.; Lyubimova, Anastasiya; Fraboni, Americo J.; Bejcek, Lauren P.; Villa, Juan A.; Gallicchio, Emilio; Murelli, Ryan P.; Tavis, John E. published the article 《Amide-containing α-hydroxytropolones as inhibitors of hepatitis B virus replication》 about this compound( cas:1827-27-6 ) in Antiviral Research. Keywords: hepatitis B virus replication amide alpha hydroxytropolone; Hepatitis B Virus; Molecular modeling; Ribonuclease H; α-Hydroxytropolones. Let’s learn more about this compound (cas:1827-27-6).

The Hepatitis B Virus (HBV) RNase H (RNaseH) is a promising but unexploited drug target. Here, we synthesized and analyzed a library of 57 amide-containing α-hydroxytropolones (αHTs) as potential leads for HBV drug development. Fifty percent effective concentrations ranged from 0.31 to 54μM, with selectivity indexes in cell culture of up to 80. Activity against the HBV RNaseH was confirmed in semi-quant. enzymic assays with recombinant HBV RNaseH. The compounds were overall poorly active against human RNase H1, with 50% inhibitory concentrations of 5.1 to >1,000μM. The aHTs had modest activity against growth of the fungal pathogen Cryptococcus neoformans, but had very limited activity against growth of the Gram – bacterium Escherichia coli and the Gram + bacterium Staphylococcus aureus, indicating substantial selectivity for HBV. A mol. model of the HBV RNaseH templated against the Ty3 RNaseH was generated. Docking the compounds to the RNaseH revealed the anticipated binding pose with the divalent cation coordinating motif on the compounds chelating the two Mn++ ions modeled into the active site. These studies reveal that that amide aHTs can be strong, specific HBV inhibitors that merit further assessment toward becoming anti-HBV drugs.

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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

SDS of cas: 1827-27-6. 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: 5-Amino-2-fluoropyridine, is researched, Molecular C5H5FN2, CAS is 1827-27-6, about Design, synthesis and evaluation of pyrazolopyrimidinone derivatives as novel PDE9A inhibitors for treatment of Alzheimer’s disease. Author is Zhang, Pei; Jiang, Mei-Yan; Le, Mei-Ling; Zhang, Bei; Zhou, Qian; Wu, Yinuo; Zhang, Chen; Luo, Hai-Bin.

Phosphodiesterase-9 (PDE9) is a promising target for the treatment of Alzheimer’s disease (AD). To discover efficient PDE9 inhibitors with good metabolic stability and solubility, a series of novel pyrazolopyrimidinone derivatives were designed with the assistance of mol. docking and dynamics simulations. All the fourteen synthesized compounds gave excellent inhibition ratio against PDE9 at 10 nM. Compound (R)-N-(1H-benzo[d]imidazol-5-yl)-2-((1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo [3,4-d]pyrimidin-6-yl)amino)propanamide with the IC50 of 2.0 nM against PDE9, showed good metabolic stability (t1/2 of 57 min) in the RLM as well as good solubility (195 mg/L). The anal. on binding modes of targeted compounds may provide insight for further structural modification.

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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.Quality Control of 5-Amino-2-fluoropyridine.Panov, Maxim S.; Voskresenska, Valentyna D.; Ryazantsev, Mikhail N.; Tarnovsky, Alexander N.; Wilson, R. Marshall published the article 《5-Azido-2-aminopyridine, a New Nitrene/Nitrenium Ion Photoaffinity Labeling Agent That Exhibits Reversible Intersystem Crossing between Singlet and Triplet Nitrenes》 about this compound( cas:1827-27-6 ) in Journal of the American Chemical Society. Keywords: azidodiethylaminopyridine nitrene nitrenium ion photoaffinity labeling agent reversible intersystem. Let’s learn more about this compound (cas:1827-27-6).

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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Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 5-Amino-2-fluoropyridine(SMILESS: NC1=CN=C(C=C1)F,cas:1827-27-6) is researched.Computed Properties of C4H6N2O2S. The article 《Synthesis and in vitro evaluation of [18F]BMS-754807: A potential PET ligand for IGF-1R》 in relation to this compound, is published in Bioorganic & Medicinal Chemistry Letters. Let’s take a look at the latest research on this compound (cas:1827-27-6).

Radiosynthesis and in vitro evaluation of [18F](S)-1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide ([18F]BMS-754807 or [18F] I) a specific IGF-1R inhibitor was performed. [18F]I demonstrated specific binding in vitro to human cancer tissues. Synthesis of reference standard II(X= F) and corresponding bromo derivative II(X = X = Br), the precursor for radiolabeling were achieved from 2,4-dichloropyrrolo[2,1-f][1,2,4]triazine in three steps with 50% overall yield. The radioproduct was obtained in 8% yield by reacting 1a with [18F]TBAF in DMSO at 170 °C at high radiochem. purity and specific activity (1-2 Ci/μmol, N = 10). The proof of concept of IGF-IR imaging with [18F]I was demonstrated by in vitro autoradiog. studies using pathol. identified surgically removed grade IV glioblastoma, breast cancer and pancreatic tumor tissues. These studies indicate that [18F]I can be a potential PET tracer for monitoring IGF-1R.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Amino-2-fluoropyridine, is researched, Molecular C5H5FN2, CAS is 1827-27-6, about Utility of MetaSite in improving metabolic stability of the neutral indomethacin amide derivative and selective cyclooxygenase-2 inhibitor 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-N-phenethyl-acetamide, the main research direction is NSAID indomethacin amide derivative indolacetamide preparation pharmacokinetics modeling.COA of Formula: C5H5FN2.

Prediction of the metabolic sites for new compounds, synthesized or virtual, is important in the rational design of compounds with increased resistance to metabolism The aim of the present investigation was to use rational design together with MetaSite, an in silico tool for predicting metabolic soft spots, to synthesize compounds that retain their pharmacol. effects but are metabolically more stable in the presence of cytochrome P 450 enzymes. The model compound for these studies was the phenethyl amide (1) derivative of the nonsteroidal anti-inflammatory drug (NSAID) indomethacin. Unlike the parent NSAID, 1 is a potent and selective cyclooxygenase-2 (COX-2) inhibitor and nonulcerogenic anti-inflammatory agent in the rat. This pharmacol. benefit is offset by the finding that 1 is very unstable in rat and human microsomes because of extensive P 4503 A4/2D6-mediated metabolism on the phenethyl group, exptl. observations that were accurately predicted by MetaSite. The information was used to design analogs with polar (glycinyl) and/or electron-deficient (fluorophenyl, fluoropyridinyl) amide substituents to reduce metabolism in 1. MetaSite correctly predicted the metabolic shift from oxidation on the amide substituent to O-demethylation for these compounds, whereas rat and human microsomal stability studies and pharmacokinetic assessments in the rat confirmed that the design tactics for improving pharmacokinetic attributes of 1 had worked in our favor. In addition, the fluorophenyl and pyridinyl amide derivatives retained the potent and selective COX-2 inhibition demonstrated with 1. Overall, the predictions from MetaSite gave useful information leading to the design of new compounds with improved metabolic properties.

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Pyrazine – Wikipedia,
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