Category: pyridine-derivatives

Yakhontov, L. N.; Azimov, V. A.; Lapan, E. I. published the artcile< Reactivity of isomeric azaindoles>, HPLC of Formula: 23612-36-4, the main research area is indoles aza; pyridines; azaindoles; furopyridines; pyrrolopyridines; pyridines pyrrolo.

Treatment of the pyridine I (R = 6-Cl) with NH3 in EtOH 4 hrs. at 200° yielded 71.5% 5-azaindoline (II) (R = 6-Cl, R1 = H), m. 106-7° (EtOAc), b1·5 152-4°. The azabenzofuran III (R = 6-OH) heated 8 hrs. at 190° with 3 molar equivalents PhCH2NH2 yielded 72% II (R = 6-OH, R1 = CH2Ph), m. 187-8° (dioxane), transformed by heating 5 hrs. at 150° with POCl3 into II (R = 6-Cl, R1 = CH2Ph), m. 75-6° (EtOAc). This reduced over Pd-C gave II (R = R1 = H) (IV), m. 102-3° (C6H12), dehydrogenated by heating 15 min. (N atm.) with 9% Pd-C at 2 5-25° to yield 70.5% 5-azaindole (V), m. 109.5-10.0° (H2O). III (R = OH) heated 8 hrs. at 250° with PhNH2 gave 78.8% II (R = 6-OH, R1 = Ph), m. 215-16° (EtOH), converted via II (R = 6-Cl, R1 = Ph), m. 99-100° (EtOH) into II (R = H, R1 = Ph), m. 59-60° (petroleum ether) and dehydrogenated at 255-65° to yield 80.7% 1-phenyl-5-azaindole (VI), m. 58-9° (petroleum ether). Condensation of 2-methyl-3-nitropyridine with (CO2Et)2 in the presence of EtOK in C6H6 at 25° 24 hrs. and the product, 70% Et3-nitro-2-pyridylpyruvate, m. 126-7°, reduced in EtOH over 9% Pd-C gave quant. Et 4-azaindole-2-carboxylate, m. 173-3.5°, saponified to 4-azaindole-2-carboxylic acid (VII), m. 302-3° (decomposition). Similarly, 2-methyl-3-nitro-6-ethoxypyridine, m. 39-40°, gave 58.8% Et 3-nitro-6-ethoxy-2-pyridylpyruvate, m. 131-2° (alc.), which gave 93% Et 5-ethoxy-4-azaindole-2-carboxylate, m. 148-9.5° (alc.) and then, via the corresponding acid, m. 300° (decomposition), 5-ethoxy-4-azaindole (VIII), m. 148-50°. Nitration, bromination, cyanomethylation and the Mannich reaction were used as electrolytic substitution reactions and carried out under conditions which had given the best yields for the corresponding 7-azaindole derivatives The cyanomethylated products were converted into azoindolyl-3-acetic acids. The Mannich reactions were carried out with 20% paraformaldehyde and 3 molar equivalents Me2NH.-HCl in refluxing BuOH; % yields and m.p. for the 3-substituted products were tabulated. π-Electron d. effects were discussed.

Tetrahedron Letters published new progress about Reactivity (chemical). 23612-36-4 belongs to class pyridine-derivatives, and the molecular formula is C7H5BrN2, HPLC of Formula: 23612-36-4.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Carnizello, Andrea P.; Alves, Jacqueline M.; Pereira, Daiane E.; Campos, Jacqueline C. L.; Barbosa, Marilia I. F.; Batista, Alzir A.; Tavares, Denise C. published the artcile< Study of the cytotoxic and genotoxic potential of the carbonyl ruthenium(II) compound, ct-[RuCl(CO)(dppb)(bipy)]PF6 [dppb = 1,4-bis(diphenylphosphino)butane and bipy = 2,2′-bipyridine], by in vitro and in vivo assays>, SDS of cas: 366-18-7, the main research area is cytotoxicity genotoxicity carbonyl ruthenium assay; carbonyl ruthenium complexes; comet assay; genotoxic potential; micronucleus test.

Considering the promising previous results of ct-[RuCl(CO)(dppb)(bipy)]PF6 (where dppb = 1,4-bis(diphenylphosphino)butane and bipy = 2,2′-bipyridine) as an antitumor agent, novel biol. assays evaluating its toxicogenic potential were performed. The genotoxicity of the compound was evaluated by the in vitro micronucleus test (V79, Chinese hamster lung fibroblasts; HepG2, hepatocellular carcinoma cells), in vivo bone marrow micronucleus test and comet assay in hepatocytes (Swiss mice). The animals were treated with 0.63, 1.25, 2.5 and 5.0 mg/kg body weight (bw) of the compound Neg. (water) and pos. (cisplatin, 1.5 mg/kg bw; Me methanesulfonate, 40 mg/kg bw) controls were included. The parameters considered in the comet assay were the percentage of tail DNA, tail moment and tail length. The results of the in vitro micronucleus tests showed the absence of genotoxicity in V79 cells, while the compound was genotoxic in HepG2 cells at a concentration of 1.25 microM. In the in vivo micronucleus test, the compound was not genotoxic at the different doses evaluated. In the comet assay, only the dose of 5.0 mg/kg bw resulted in a significant increase in the frequency of DNA damage in hepatocytes when compared to the neg. control. The genotoxic effect observed in HepG2 cells and in the liver comet assay indicates that the compound was metabolized by hepatic cells.

Journal of Applied Toxicology published new progress about Analysis. 366-18-7 belongs to class pyridine-derivatives, and the molecular formula is C10H8N2, SDS of cas: 366-18-7.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

An, Ju Hyeon; Kim, Kyu Dong; Lee, Jun Hee published the artcile< Highly Chemoselective Deoxygenation Of N-Heterocyclic N-Oxides Using Hantzsch Esters As Mild Reducing Agents>, Computed Properties of 93-60-7, the main research area is deoxygenated nitrogen heterocycle green preparation chemoselective; heterocycle nitrogen oxide deoxygenation Hantzsch ester metallaphotocatalyst.

A highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant to afford deoxygenated N-heterocycles I [R = 6-OMe, 6-Cl, 2-Ph, etc.], II [R1 = H, 5-Br; X = CH, N] and III [R2 = 3-Ph, 2,6-Cl2, pyridin-2-yl, etc.] were reported. Despite the feasibility of catalyst-free conditions, most of these deoxygenations could be completed within a few minutes using only a tiny amount of a catalyst. This technol. also allowed for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompassed a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups and halogens, which provided access to the corresponding compounds I, II and III in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Journal of Organic Chemistry published new progress about Amine oxides Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (heteroarene). 93-60-7 belongs to class pyridine-derivatives, and the molecular formula is C7H7NO2, Computed Properties of 93-60-7.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Wu, Gaorong; Fu, Xiaopan; Wang, Yangyang; Deng, Kezuan; Zhang, Lili; Ma, Tao; Ji, Yafei published the artcile< C-H Borylation of Diphenylamines through Adamantane-1-carbonyl Auxiliary by BBr3>, Category: pyridine-derivatives, the main research area is ortho carbon hydrogen bond borylation phenylamine adamantanecarbonyl directed; isotope effect borylation kinetics phenylamine adamantanecarbonyl directed; boronate ester phenylamine derivative preparation reactivity; crystal structure chlorophenyl dioxaborolanylphenyl adamantanecarboxamide; mol structure chlorophenyl dioxaborolanylphenyl adamantanecarboxamide.

A method for ortho-C-H borylation of diphenylamines using BBr3 as the B source is reported. The noncatalytic adamantane-1-carbonyl directed reaction exhibited site exclusivity and good functional group tolerance. Generally, the borylation occurred at the more electron-rich aromatic ring and the borylated products could be converted to various useful intermediates. Besides, the derived arylation and removal of auxiliary of the product could be achieved in a 1-pot fashion.

Organic Letters published new progress about Addition reaction kinetics (borylation). 22961-45-1 belongs to class pyridine-derivatives, and the molecular formula is C11H10N2, Category: pyridine-derivatives.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Elawa, Sherif; Mirdell, Robin; Farnebo, Simon; Tesselaar, Erik published the artcile< Skin blood flow response to topically applied methyl nicotinate: Possible mechanisms.>, Synthetic Route of 93-60-7, the main research area is capillary capacity; laser speckle contrast imaging; methyl nicotinate; microcirculation; tissue viability.

BACKGROUND: Methyl nicotinate (MN) induces a local cutaneous erythema in the skin and may be valuable as a local provocation in the assessment of microcirculation and skin viability. The mechanisms through which MN mediates its vascular effect are not fully known. The aim of this study was to characterize the vasodilatory effects of topically applied MN and to study the involvement of nitric oxide (NO), local sensory nerves, and prostaglandin-mediated pathways. METHODS: MN was applied on the skin of healthy subjects in which NO-mediated (L-NMMA), nerve-mediated (lidocaine/prilocaine), and cyclooxygenase-mediated (NSAID) pathways were selectively inhibited. Microvascular responses in the skin were measured using laser speckle contrast imaging (LSCI). RESULTS: NSAID reduced the MN-induced perfusion increase with 82% (P < .01), whereas lidocaine/prilocaine reduced it with 32% (P < .01). L-NMMA did not affect the microvascular response to MN. CONCLUSION: The prostaglandin pathway and local sensory nerves are involved in the vasodilatory actions of MN in the skin. Skin research and technology : International Society for Skin Imaging (ISSI) published new progress about 93-60-7. 93-60-7 belongs to class pyridine-derivatives, and the molecular formula is C7H7NO2, Synthetic Route of 93-60-7.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Shi, Yinyin; Wang, Yue; Huang, Zhefan; Zhang, Fangjun; Shao, Yinlin published the artcile< tBuOLi-Promoted Hydroboration of Esters and Epoxides>, Computed Properties of 93-60-7, the main research area is ester lactone epoxide hydroboration chemoselective lithium tertbutoxide catalyst; alc preparation.

Com. available and inexpensive lithium tert-butoxide (tBuOLi) acts as a good precatalyst for the hydroboration of esters, lactones, and epoxides using pinacolborane as a borylation agent. Functional groups such as cyano-, nitro-, amino-, vinyl, and alkynyl are unaffected under the presented hydroboration process, representing high chemoselectivity. This transformation has also been effectively applied to the synthesis of key intermediates of Erlotinib and Cinacalcet. Preliminary investigations of the mechanism show that the hydroboration proceeds through the in situ formed BH3 species.

ACS Omega published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 93-60-7 belongs to class pyridine-derivatives, and the molecular formula is C7H7NO2, Computed Properties of 93-60-7.

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

Takale, Balaram S.; Thakore, Ruchita R.; Handa, Sachin; Gallou, Fabrice; Reilly, John; Lipshutz, Bruce H. published the artcile< A new, substituted palladacycle for ppm level Pd-catalyzed Suzuki-Miyaura cross couplings in water>, Recommanded Product: 3-Chloro-2-methoxypyridine, the main research area is biarene preparation green chem; halide aryl boronic acid Suzuki Miyaura coupling palladium catalyst.

A newly engineered palladacycle that contains substituents on the biphenyl rings along with the ligand HandaPhos is especially well-matched to an aqueous micellar medium, enabling valued Suzuki-Miyaura coupling of aryl halides RX (R = 2-O2NC6H4, 1-benzothiophen-2-yl, 2-fluoropyridin-3-yl, etc.; X = Cl, Br, I) and aryl boronic acids R1B(OH)2 (R1 = 4-ClC6H4, 1-benzofuran-2-yl, pyren-1-yl, etc.) to be run not only in water under mild conditions, but at 300 ppm of Pd catalyst. This general methodol. has been applied to several targets in the pharmaceutical area. Multiple recyclings of the aqueous reaction mixture involving both the same as well as different coupling partners are demonstrated. Low temperature microscopy (cryo-TEM) indicates the nature and size of the particles acting as nanoreactors. Importantly, given the low loadings of Pd invested per reaction, ICP-MS analyses of residual palladium in the products show levels to be expected that are well within FDA allowable limits.

Chemical Science published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 13472-84-9 belongs to class pyridine-derivatives, and the molecular formula is C6H6ClNO, Recommanded Product: 3-Chloro-2-methoxypyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Dai, Qiang; Li, Wenbo; Li, Zhiming; Zhang, Junliang published the artcile< P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P-C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides>, Recommanded Product: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole, the main research area is phosphine chiral palladium catalyzed arylation phosphine oxide aryl bromide; chiral aryldiphosphine oxide preparation crystal structure; mol structure chiral aryl diphosphine oxide palladium sulfinamidephosphine; palladium sulfinamidephosphine chiral complex preparation crystal structure.

The development of transition-metal-catalyzed methods for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Herein, the authors present a direct Pd/Xiao-Phos-catalyzed cross-coupling reaction of easily accessible secondary phosphine oxides and aryl bromides, which provides rapid access to P-chiral phosphine oxides. The reaction proceeds efficiently with a wide array of reaction partners to deliver various tertiary phosphine oxides in up to 96% yield and 97% ee. Also, the synthesis of DiPAMP ligand and its analogs was also realized, which demonstrates a suitable pathway to switching the branched chain of DiPAMP.

Journal of the American Chemical Society published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 1416819-91-4 belongs to class pyridine-derivatives, and the molecular formula is C13H15F3N2O, Recommanded Product: (S)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Su, Xuxian; Wang, Wen-Jin; Cao, Qian; Zhang, Hang; Liu, Bin; Ling, Yuyi; Zhou, Xiaotong; Mao, Zong-Wan published the artcile< A Carbonic Anhydrase IX (CAIX)-Anchored Rhenium(I) Photosensitizer Evokes Pyroptosis for Enhanced Anti-Tumor Immunity>, Formula: C6H8N2, the main research area is CAIX ruthenium photosensitizer preparation cancer PDT pyroptosis immunity; anti-tumor immunity; carbonic anhydrase IX targeting; metallodrugs; photodynamic therapy; pyroptosis.

An ideal cancer treatment should not only destroy primary tumors but also improve the immunogenicity of the tumor microenvironment to achieve a satisfactory anti-tumor immune effect. We designed a carbonic anhydrase IX (CAIX)-anchored rhenium(I) photosensitizer, named CA-Re, that not only performs type-I and type-II photodynamic therapy (PDT) with high efficiency under hypoxia (nanomolar-level phototoxicity), but also evokes gasdermin D (GSDMD) mediated pyroptotic cell death to effectively stimulate tumor immunogenicity. CA-Re could disrupt and self-report the loss of membrane integrity simultaneously. This promoted the maturation and antigen-presenting ability of dendritic cells (DCs), and fully activated T cells dependent adaptive immune response in vivo, eventually eliminating distant tumors at the same time as destroying primary tumors. To the best of our knowledge, CA-Re is the first metal complex-based pyroptosis inducer.

Angewandte Chemie, International Edition published new progress about Adaptive immunity. 3731-53-1 belongs to class pyridine-derivatives, and the molecular formula is C6H8N2, Formula: C6H8N2.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem