Category: 1827-27-6

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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Pyrazine – Wikipedia,
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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.Recommanded Product: 2-Amino-4,5-dihydrothiazole-4-carboxylic acid. The article 《Three Arene-Ru(II) compounds of 2-halogen-5-aminopyridine: Synthesis, characterization, and cytotoxicity》 in relation to this compound, is published in Applied Organometallic Chemistry. Let’s take a look at the latest research on this compound (cas:1827-27-6).

Three novel compounds, (η6-p-cymene)RuCl2(2-fluoro-5-aminopyridine) (compound 1), (η6-p-cymene)RuCl2(5-amino-2-chloropyridine) (compound 2) and (η6-p-cymene)RuCl2(2-bromo- 5-aminopyridine) (compound 3), were synthesized and characterized. The structures of compound 1 and 3 were determined by x-ray diffraction, showing a distorted piano-stool type of geometry with similar bond lengths and angles around the Ru. Compound 2 exhibited moderate in vitro activity against A549 and MCF-7 human cancer cells, the other two lower activities. The UV-visible and fluorescent absorption titrations showed that the three compounds bonded with CT-DNA in a minor groove. The intrinsic binding constants (Kb) were calculated to be 2.13(±0.03) × 105 M-1, 2.89(±0.03) × 105 M-1 and 2.45(±0.03) × 105 M-1 for compound 1, 2 and 3, resp., by using UV-visible absorption titrations data. Among the three compound, the highest value of intrinsic binding constant of compound 2 was consistent with its high cytotoxicity against A549 and MCF-7 human cancer cells in vitro.

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Pyrazine – Wikipedia,
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Product Details 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 Synthesis, biological evaluation and 3D-QSAR studies of 1,2,4-triazole-5-substituted carboxylic acid bioisosteres as uric acid transporter 1 (URAT1) inhibitors for the treatment of hyperuricemia associated with gout. Author is Wu, Jing-wei; Yin, Ling; Liu, Yu-qiang; Zhang, Huan; Xie, Ya-fei; Wang, Run-ling; Zhao, Gui-long.

Bromonaphthylmethyltriazolyl thioether lesinurad analogs and bioisosteres such as I were prepared as inhibitors of uric acid transporter 1 (URAT1) for potential use in treating hyperuricemia and gout. I inhibited URAT1 with an IC50 value of 32 nM, 225-fold lower than lesinurad. The pharmacophore for the lesinurad analogs was determined using a 3D-QSAR pharmacophore model; the hypothesis was validated by three methods (cost anal., Fisher’s randomization and leave-one-out).

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Rewcastle, Gordon W.; Denny, William A.; Winters, R. Thomas; Colbry, Norman L.; Showalter, H. D. Hollis published the article 《Synthesis of 6-substituted pyrido[3,4-d]pyrimidin-4(3H)-ones via directed lithiation of 2-substituted 5-aminopyridine derivatives》. Keywords: pyridopyrimidinone preparation; pyrimidinone pyrido preparation; aminopyridine lithiation carboxylation.They researched the compound: 5-Amino-2-fluoropyridine( cas:1827-27-6 ).Synthetic Route of C5H5FN2. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:1827-27-6) here.

Directed lithiation of Boc or pivaloyl derivatives of 2-substituted 5-aminopyridines I (R = Cl, F, OMe, R1 = COnCMe3, X = H, n = 1, 2) with BuLi-TMEDA in di-Et ether at -10°C gave 4-lithio derivatives which were quenched with CO2 to give the analogous C-4 carboxylic acids I (X = CO2H). Hydrolysis of the protecting groups with either TFA or aqueous KOH gave 2-substituted 5-aminopyridine-4-carboxylic acids I (R1 = H, X = CO2H) which were converted to 6-substituted pyrido[3,4-d]pyrimidin-4(3H)-ones II by reaction with formamide or, more optionally, formamidine acetate. Boc protected aminopyridines provided the best overall results, with synthesis of these derivatives best achieved by direct reaction of the aminopyridine with di-tert-Bu dicarbonate in the absence of added base.

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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 Design, synthesis and biological evaluation of indole-2-carboxylic acid derivatives as IDO1/TDO dual inhibitors, published in 2020-02-15, which mentions a compound: 1827-27-6, Name is 5-Amino-2-fluoropyridine, Molecular C5H5FN2, Product Details of 1827-27-6.

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO) are involved in the key steps of tryptophan metabolism and are potential new targets for tumor immunotherapy. In this work, a variety of indole-2-carboxylic acid derivatives I (R1 = H, 7-F, NHAc, etc.; X = NH, NMe, S; Y = NH, S, -NHCH2-, etc.; Ar = 4-F-3-Cl-C6H3, 4-F-3-OMe-C6H3, 3-Cl-3-OMe-C6H3, etc.) were synthesized, and their inhibitory activities against both enzymes along with structure-activity relationships were investigated. As a result, a number of 6-acetamido-indole-2-carboxylic acid derivatives were found to be potent dual inhibitors with IC50 values at low micromolar levels. Among them, compound I (R1 = 6-NHAc, X = N, Y = NH, Ar = 3,4-di-F-C6H3) was the most potent inhibitor with an IC50 value of 1.17μM for IDO1, and 1.55μM for TDO, resp. In addition, a para-benzoquinone derivative II, resulted from the oxidation of compound I (R1 = 6-NHEt, X = NH, Y = NH, Ar = 4-F-3-Cl-C6H3), was also identified and it showed strong inhibition against the two enzymes with IC50 values at the double digit nanomolar level. Using mol. docking and mol. dynamic simulations, authors predicted the binding modes of this class of compounds within IDO1 and TDO binding pocket. The results provide insights for further structural optimization of this series of IDO1/TDO dual inhibitors.

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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 3-Phenylazopyridines, published in 1970, which mentions a compound: 1827-27-6, Name is 5-Amino-2-fluoropyridine, Molecular C5H5FN2, Formula: C5H5FN2.

Hydrogenation of 2-substituted I (X = NO2), under CO2, in MeOH with Pd/C gave I (X = NH2) (II) (method A). II were also prepared by reduction of I (X = NO2) with Fe dust in aqueous AcOH (method B). The II prepared were (R, method of preparation, and % yield given): Me, A, 95; SMe, A, 85; F, B, 70; Cl, B, 73.5; Br, B, 81; iodo, B, 86; MeO, A/B, 90.1/80.5; and AcNH, A/B, 90/70. A mixture of PhNO and II (R = MeO) kept 20 min in 50% aqueous NaOH gave III (R = OMe) (method A). In method B the above reaction was carried out at room temperature in AcOH. Similarly prepared were 7 other III analogs.

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Pyrazine – Wikipedia,
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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).Recommanded Product: 5-Amino-2-fluoropyridine. 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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Pyrazine – Wikipedia,
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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: 1827-27-6, is researched, SMILESS is NC1=CN=C(C=C1)F, Molecular C5H5FN2Journal, Article, Research Support, Non-U.S. Gov’t, Organic Letters called Sulfonamide Synthesis via Calcium Triflimide Activation of Sulfonyl Fluorides, Author is Mukherjee, Paramita; Woroch, Cristian P.; Cleary, Leah; Rusznak, Mark; Franzese, Ryan W.; Reese, Matthew R.; Tucker, Joseph W.; Humphrey, John M.; Etuk, Sarah M.; Kwan, Sabrina C.; am Ende, Christopher W.; Ball, Nicholas D., the main research direction is calcium triflimide sulfonyl fluoride amine nucleophilic addition; sulfonamide synthesis.HPLC of Formula: 1827-27-6.

A method using calcium triflimide [Ca(NTf2)2] as a Lewis acid to activate sulfonyl fluorides toward nucleophilic addition with amines is described. The reaction converts a wide array of sterically and electronically diverse sulfonyl fluorides and amines into the corresponding sulfonamides in good yield.

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Pyrazine – Wikipedia,
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Application of 1827-27-6. 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 Design, synthesis and biological evaluation of indole-2-carboxylic acid derivatives as IDO1/TDO dual inhibitors. Author is Cui, Guonan; Lai, Fangfang; Wang, Xiaoyu; Chen, Xiaoguang; Xu, Bailing.

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO) are involved in the key steps of tryptophan metabolism and are potential new targets for tumor immunotherapy. In this work, a variety of indole-2-carboxylic acid derivatives I (R1 = H, 7-F, NHAc, etc.; X = NH, NMe, S; Y = NH, S, -NHCH2-, etc.; Ar = 4-F-3-Cl-C6H3, 4-F-3-OMe-C6H3, 3-Cl-3-OMe-C6H3, etc.) were synthesized, and their inhibitory activities against both enzymes along with structure-activity relationships were investigated. As a result, a number of 6-acetamido-indole-2-carboxylic acid derivatives were found to be potent dual inhibitors with IC50 values at low micromolar levels. Among them, compound I (R1 = 6-NHAc, X = N, Y = NH, Ar = 3,4-di-F-C6H3) was the most potent inhibitor with an IC50 value of 1.17μM for IDO1, and 1.55μM for TDO, resp. In addition, a para-benzoquinone derivative II, resulted from the oxidation of compound I (R1 = 6-NHEt, X = NH, Y = NH, Ar = 4-F-3-Cl-C6H3), was also identified and it showed strong inhibition against the two enzymes with IC50 values at the double digit nanomolar level. Using mol. docking and mol. dynamic simulations, authors predicted the binding modes of this class of compounds within IDO1 and TDO binding pocket. The results provide insights for further structural optimization of this series of IDO1/TDO dual inhibitors.

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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: 1827-27-6, is researched, Molecular C5H5FN2, about 2-Aminoadipic Acid-C(O)-Glutamate Based Prostate-Specific Membrane Antigen Ligands for Potential Use as Theranostics, the main research direction is aminoadipic acid glutamate prostate specific membrane antigen theranostic.Formula: C5H5FN2.

The design and synthesis of prostate specific membrane antigen (PSMA) ligands derived from 2-aminoadipic acid, a building block that has not previously been used to construct PSMA ligands, are reported. The effects of both the linker length and of an N-substituent of our PSMA ligands were probed, and X-ray structures of five of these ligands bound to PSMA were obtained. Among the ligands disclosed herein, I showed the highest inhibitory activity for PSMA. As ligand I can readily be radiolabeled since its fluorine atom is adjacent to the nitrogen atom of its pyridine ring, the use of this and related compounds as theranostics can be pursued.

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Reference:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem