Category: 22280-62-2

Hikawa, Hidemasa; Nakayama, Taku; Nakamura, Shunki; Kikkawa, Shoko; Azumaya, Isao published the artcile< Dehydrative amination of benzhydrols with electron-withdrawing group-substituted 2-aminopyridines utilizing Au(III)/TPPMS catalyst system in water>, Synthetic Route of 22280-62-2, the main research area is benzyl aminopyridine preparation; benzhydrol aminopyridine dehydrative amination gold sodium diphenylphosphinobenzene sulfonate water.

Authors report a method for gold(III)/sodium diphenylphosphinobenzene-3-sulfonate (TPPMS)-catalyzed direct amination of benzhydrols using 2-aminopyridines with poor nucleophilic character in water. Various functional groups such as electron-withdrawing nitro, cyano and halogen groups were tolerated well to form the desired N-benzylated 2-aminopyridine compounds On the basis of mechanistic studies including kinetic profiles, Hammett study and isotope effects, authors propose a pathway in which a Lewis acidic gold cation species activates the sp3 C-O bond of the alc. in the rate-determining step.

Organic & Biomolecular Chemistry published new progress about Amination (dehydrative). 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Synthetic Route of 22280-62-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Li, Yibiao; Huang, Shuo; Liao, Chunshu; Shao, Yan; Chen, Lu published the artcile< Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridines and acetamidine hydrochloride>, Quality Control of 22280-62-2, the main research area is aminopyridine preparation chemoselective green chem; fluoropyridine acetamidine hydrochloride amination.

An efficient method for the synthesis of 2-aminopyridine derivatives I (R = 3-I, 3-Cl-5-I, 5-NO2-6-CH3, etc.; R1 = NH2) through the nucleophilic substitution and hydrolysis of 2-fluoropyridines I (R1 = F) and acetamidine hydrochloride under catalyst-free conditions has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents such as 5-chloro-2,4-difluoropyrimidine and 2-fluoropyrazine can also complete the reaction via these reaction conditions and yield the target products 5-chloro-4-fluoropyrimidin-2-amine and pyrazin-2-amine resp.

Organic & Biomolecular Chemistry published new progress about Amination (chemoselective). 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Quality Control of 22280-62-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Andaloussi, Mounir; Moreau, Emmanuel; Masurier, Nicolas; Lacroix, Jacques; Gaudreault, Rene C.; Chezal, Jean-Michel; El Laghdach, Anas; Canitrot, Damien; Debiton, Eric; Teulade, Jean-Claude; Chavignon, Olivier published the artcile< Novel imidazo[1,2-a]naphthyridinic systems (Part 1): Synthesis, antiproliferative and DNA-intercalating activities>, Safety of 6-Amino-3-nitro-2-picoline, the main research area is imidazonaphthonaphthyridine preparation antiproliferative DNA intercalation.

Novel imidazo[1,2-a]naphthyridine systems were obtained from Friedlaender’s reaction in imidazo[1,2-a]pyridine series. The compounds were evaluated for their antitumor activity in the NCIs in vitro human tumor cell line screening panel. Among them, 7,8-dihydroimidazo[1,2-a]naphtho[2,1-g][1,5]naphthyridine and 8,9-dihydroimidazo[1,2-h]naphtho[1,2-b][1,7]naphthyridine exhibited in vitro activity comparable to anticancer agent such as amsacrine. Their mechanism of cytotoxic action was unrelated to poisoning or inhibiting abilities against topo1. On the contrary, a direct intercalation of the drugs into DNA was observed by electrophoresis on agarose gel.

European Journal of Medicinal Chemistry published new progress about Cytotoxic agents. 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Safety of 6-Amino-3-nitro-2-picoline.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Song, Pinrao; Chen, Ming; Ma, Xiaodong; Xu, Lei; Liu, Tao; Zhou, Yubo; Hu, Yongzhou published the artcile< Identification of novel inhibitors of Aurora A with a 3-(pyrrolopyridin-2-yl)indazole scaffold>, Application In Synthesis of 22280-62-2, the main research area is inhibitor Aurora pyrrolopyridinylindazole scaffold; Antiproliferative agents; Aurora A inhibitors; Cell cycle profile; Pyrrolopyridin-indazoles; Selectivity.

A novel series of 3-(pyrrolopyridin-2-yl)indazole derivatives were synthesized and biol. evaluated for their anti-proliferative effects on five human cancer cell lines. As a result, all of them exhibited vigorous potency against HL60 cell line with IC50 values ranging from singe digital nanomolar to micromolar level. Besides, a majority of them displayed modest to good antiproliferative activities against the other four cell lines, including KB, SMMC-7721, HCT116, and A549. Particularly, compound 2y, as the most distinguished one in this series, demonstrated IC50 values of 8.3 nM and 1.3 nM against HL60 and HCT116 cell lines, resp. Afterwards, for exploring the mol. target, compounds2d, 2g and 2y were further selected to evaluate the inhibitory activities against a panel of kinases. Finally, they were identified to be targeting Aurora A kinase with significant selectivity over other kinases, such as CHK1, CDK2, MEK1, GSK3β, BRAF, IKKβ and PKC.

Bioorganic & Medicinal Chemistry published new progress about Antitumor agents. 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Application In Synthesis of 22280-62-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Yang, Jiao; Chen, Kai; Zhang, Guo; Yang, Qiu-Yuan; Li, Yue-Shan; Huang, Shen-Zhen; Wang, Yan-Lin; Yang, Wei; Jiang, Xiao-Juan; Yan, Heng-Xiu; Zhu, Jing-Qiang; Xiang, Rong; Luo, You-Fu; Li, Wei-Min; Wei, Yu-Quan; Li, Lin-Li; Yang, Sheng-Yong published the artcile< Structural optimization and structure-activity relationship studies of N-phenyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-amine derivatives as a new class of inhibitors of RET and its drug resistance mutants>, Application In Synthesis of 22280-62-2, the main research area is phenyldihydro pyrimido oxazinamine derivative preparation RET inhibitor cancer; Drug resistance mutant; Medullary thyroid cancer; RET kinase; Structure-activity relationship.

The RET tyrosine kinase is an important therapeutic target for medullary thyroid cancer (MTC), and drug resistance mutations of RET, particularly V804M and V804L, are a main challenge for the current targeted therapy of MTC based on RET inhibitors. In this investigation, we report the structural optimization and structure-activity relationship studies of N-phenyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-amine derivatives as a new class of RET inhibitors. Among all the obtained kinase inhibitors, 1-(5-(tert-butyl)isoxazol-3-yl)-3-(4-((6,7,8,9-tetrahydropyrimido[5,4-b][1,4]oxazepin-4-yl)amino)phenyl)urea (17d) is a multi-kinase inhibitor and potently inhibits RET and its drug resistance mutants. It showed IC50 (half maximal inhibitory concentration) values of 0.010 μM, 0.015 μM, and 0.009 μM against RET-wild-type, RET-V804M, and RET-V804L, resp. 17d displayed significant anti-viability potencies against various RET-driving tumor cell lines. In a xenograft mouse model of NIH3T3-RET-C634Y, 17d exhibited potent in vivo anti-tumor activity, and no obvious toxicity was observed Mechanisms of action were also investigated by Western blot and immunohistochem. assays. Collectively, 17d could be a promising agent for the treatment of MTC, hence deserving a further investigation.

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Application In Synthesis of 22280-62-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Hajos, G.; Riedl, Z. published the artcile< Product class 5: azaindolizines with two nitrogen atoms in the five-membered ring>, Synthetic Route of 22280-62-2, the main research area is review azaindolizine preparation.

A review of preparation of azaindolizines with two nitrogen atoms in the five-membered ring. Covered reactions include ring-closure, substituent modification, substitution reactions, and other miscellaneous methods.

Science of Synthesis published new progress about Cyclization. 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Synthetic Route of 22280-62-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Talik, Tadeusz; Talik, Zofia published the artcile< Nitraminopyridines. II. Reactions of nitraminomethylpyridines with phosphorus halides>, Electric Literature of 22280-62-2, the main research area is nitramino pyridines; pyridines nitramino.

Reactions of 2-(nitramino)pyridines and 4-(nitramino)pyridines with PCl3, PCl5, PBr3, PBr5, and PI3 were studied. The nitramino group was easily exchanged for Cl, Br, or iodine. A series of chloro-, bromo-, and iodopicolines was prepared The following pyridine homologs were used as the starting material: 2-(nitramino)-3-methylpyridine (I), 2-(nitramino)-4-methylpyridine (II), 2-(nitramino)-5-methylpyridine (III), 2-(nitramino)-6-methylpyridine (IV), 4-(nitramino)-3-methylpyridine (V), 4-(nitramino)-2-methylpyridine (VI), 4-(nitramino)-2,6-dimethylpyridine (VII), and 3-(nitramino)-2,6-dimethylpyridine (VIII). The reactions were carried out in CHCl3 with 0.5 mole excess phosphorous halide at the boiling temperature Thus, a suspension of 0.01 mole nitraminomethylpyridine in 10 ml. CHCl3 was treated, under cooling, with 2.1 g. PCl3 then refluxed 1 hr., concentrated in vacuo, decomposed with ice, neutralized with NaHCO3 and steam distilled When extracted with Et2O, and the extract worked up, the distillate gave a halopicoline. The following compounds were reported (substrate, phosphones halide, product, m.p., b.p., and % yield given): I, PCl3, 2-chloro-3-methylpyridine, -, 193°, 24.1, and 2-chloro-5-nitro-3-methylpyridine (IX) 48°, -, 11.5; II, PCl3, 2-chloro-4-methylpyridine (X), -, 194°, 72.3; III, PCl3, 2-chloro-5-methylpyridine (XI), -, 86-7°/15 mm., 60.2; IV, PCl3, 2-chloro-5-nitro-6-methylpyridine (XII), 52°, -, 11.7, and 2-amino-3-nitro-6-methylpyridine (XIII), 141°, -, 6.7, and 2-amino-5-nitro-6methylpyridine, 188°, -, 13.3; V, PCl3, 4-chloro-3-methylpyridine (XIV), -, 164°, 60.2; VI, PCl3, 4-chloro-2-methylpyridine (XV), -, 162°, 72.3; VII, PCl3, 4-chloro-2,6-dimethylpyridine (XVI), -, 177°, 86.5; I, PCl5, IX, 47°, -, 26.6, and 2-amino-5-nitro-3-methylpyridine, 254°, -, 60.2; II, PCl5, X, -, 194°, 60.2; III, PCl5, XI, -, 87°/15 mm., 56.2; IV, PCl5, XII, 52°, -, 41.2, and XIII, 141°, -, 46.7; V, PCl5, XIV, -, 164°, 84.3; VI, PCl5, XV, -, 162°, 84.3; VII, PCl5, XVI, -, 177°, 86.5; I, PBr3, 2-bromo-3-methylpyridine (XVII), -, 209°, 48.5; II, PBr3, 2-bromo-4-methylpyridine (XVIII), -, 213°, 63.6, III, PBr3, 2-bromo-5-methylpyridine (XIX), 48°, -, 62.3; IV, PBr3, 2-bromo-5-nitro-6-methylpyridine (XX), 69°, -, 32.8, and 2-amino-3-nitro-6-methylpyridine (XXI), 141°, -, 20, and 2-amino-5-nitro-6-methylpyridine (XXII), 188°, -, 40; V, PBr3, PBr3, 4-bromo-3-methylpyridine (XXIII), -, 76°/15 mm., 77.1; VI, PBr3, 4-bromo-2-methylpyridine (XXIV), -, 181°, 62.3; VII, PBr3, 4-bromo-2,6-dimethylpyridine (XXV), -, 193°, 49.4; I, PBr5, XVII, -, 209°, 71.2; II, PBr5, XVIII, -, 212°, 62.3; III, PBr5, XIX, 48°, -, 62.3; IV, PBr5, XX, 69°, -, 9.4, and XXI, 141°, -, 33.3, and XXII, 188°, -, 40.0; V, PBr5, XXIII, -, 76°/15 mm., 44.5; VI, PBr5, XXIV, -, 181°, 44.5; VII, PBr5, XXV, -, 193°, 49.4; I, PI3, 2-iodo-3-methylpyridine, -, 105°, 27; II, PI3, 2-iodo-4-methylpyridine, -, 112°, 65; III, PI3, 2-iodo-5-methylpyridine, 52°, -, 69.9; V, PI3, 4-iodo-3-methylpyridine, 46°, -, 55.9; VI, PI3, 4-iodo-2-methylpyridine, 42°, -, 83.6; VII, PI3, 4-iodo-2,6-dimethylpyridine, 99°, -, 65.7. VIII did not react with phosphorus halides. Under the conditions employed, decomposition of VIII and formation of 3-amino-2,6-dimethylpyridine was observed.

Roczniki Chemii published new progress about Group 15 element halides, phosphorus halides Role: RCT (Reactant), RACT (Reactant or Reagent). 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Electric Literature of 22280-62-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Goldberg, Frederick W.; Finlay, M. Raymond V.; Ting, Attilla K. T.; Beattie, David; Lamont, Gillian M.; Fallan, Charlene; Wrigley, Gail L.; Schimpl, Marianne; Howard, Martin R.; Williamson, Beth; Vazquez-Chantada, Mercedes; Barratt, Derek G.; Davies, Barry R.; Cadogan, Elaine B.; Ramos-Montoya, Antonio; Dean, Emma published the artcile< The Discovery of 7-Methyl-2-[(7-methyl[1,2,4]triazolo[1,5-a]pyridin-6-yl)amino]-9-(tetrahydro-2H-pyran-4-yl)-7,9-dihydro-8H-purin-8-one (AZD7648), a Potent and Selective DNA-Dependent Protein Kinase (DNA-PK) Inhibitor>, Recommanded Product: 6-Amino-3-nitro-2-picoline, the main research area is AZD7648 preparation DNA protein kinase inhibitor cancer.

DNA-PK is a key component within the DNA damage response, as it is responsible for recognizing and repairing double-strand DNA breaks (DSBs) via non-homologous end joining. Historically it has been challenging to identify inhibitors of the DNA-PK catalytic subunit (DNA-PKcs) with good selectivity vs. the structurally related PI3 (lipid) and PI3K-related protein kinases. We screened our corporate collection for DNA-PKcs inhibitors with good PI3 kinase selectivity, identifying compound 1. Optimization focused on further improving selectivity while improving phys. and pharmacokinetic properties, notably co-optimization of permeability and metabolic stability, to identify compound 16 (AZD7648). Compound 16 had no significant off-target activity in the protein kinome and only weak activity vs. PI3Kα/γ lipid kinases. Monotherapy activity in murine xenograft models was observed, and regressions were observed when combined with inducers of DSBs (doxorubicin or irradiation) or PARP inhibition (olaparib). These data support progression into clin. studies (NCT03907969).

Journal of Medicinal Chemistry published new progress about Antitumor agents (potential as). 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Recommanded Product: 6-Amino-3-nitro-2-picoline.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Wandas, M.; Lorenc, J.; Kucharska, E.; Maczka, M.; Hanuza, J. published the artcile< Molecular structure and vibrational spectra of 3 (or 4 or 6)-methyl-5-nitro-2-pyridinethiones: FT-IR, FT-Raman and DFT quantum chemical calculations>, Synthetic Route of 22280-62-2, the main research area is structure vibrational spectra methylnitropyridinethione FT IR Raman DFT quantum.

IR and Raman spectra (RS) of polycrystalline 3-(or 4 or 6)-methyl-5-nitro-2-pyridinethione were measured and analyzed by d. functional theory (DFT) quantum chem. calculations The B3LYP/6-311G(2d,2p) approach was applied for both the thiol and thione tautomers due to the possibility of the formation of these two thiole forms. Mol. structures of these compounds were optimized starting from different mol. geometries of the thiol group and thione group. Two conformations of the 2-mercaptopyridine, trans and cis, were taken into account. The studied compounds appear in the solid state in the thione form. The effect of the hydrogen-bond formation in the studied compounds was considered.

Journal of Raman Spectroscopy published new progress about Conformation. 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Synthetic Route of 22280-62-2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kulkarni, Santosh S.; Newman, Amy Hauck published the artcile< Discovery of heterobicyclic templates for novel metabotropic glutamate receptor subtype 5 antagonists>, Name: 6-Amino-3-nitro-2-picoline, the main research area is quinoline benzothiazole preparation glutamate receptor antagonist SAR; pyridothiazole imidazopyridine preparation glutamate receptor antagonist SAR.

Investigation of a series of heterobicyclic compounds with essential pharmacophoric features of the metabotropic glutamate receptor 5 (mGluR5) antagonists MPEP and MTEP provided novel structural templates with sub-micromolar affinities at the mGluR5. Compound I showed antagonist activity (IC50 = 0.26 μM) in the functional assay measuring hydrolysis of phosphoinositide and may provide a new lead for further SAR investigation.

Bioorganic & Medicinal Chemistry Letters published new progress about Metabotropic glutamate receptors, group I, mGluR5 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 22280-62-2 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Name: 6-Amino-3-nitro-2-picoline.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem