Category: 62163-09-1

Nasielski, J.; Heilporn, S.; Nasielski-Hinkens, R.; Tinant, B.; Declercq, J. P. published an article in 1989, the title of the article was An unexpected ring-opening in the Reissert reaction on 2,3-diphenylquinoxaline N-oxide.SDS of cas: 62163-09-1 And the article contains the following content:

When quinoxaline-N-oxide is reacted with KCN and BzCl in H2O or MeOH; the products are 2-, 5- and 6-chloroquinoxaline and small amounts of 2-cyanoquinoxaline. Using three equivalent of Me3SiCN instead of KCN, and CH2Cl2 as the solvent, leads to a 72% yield of 2-cyanoquinoxaline. The reaction of Me3SiCN and BzCl with 2,3-diphenylquinoxaline-N-oxide leads to 2-Bz2NC6H4N:CPhCN (I). The structure of I is based on spectroscopic data and on an X-ray crystallog. anal. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).SDS of cas: 62163-09-1

The Article related to quinoxaline oxide reissert, phenylquinoxaline oxide reissert ring cleavage, crystal structure benzaliminobenzoylaniline, mol structure benzaliminobenzoylaniline, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.SDS of cas: 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On February 28, 2011, Guemues, Selcuk published an article.Synthetic Route of 62163-09-1 The title of the article was The aromaticity of substituted diazanaphthalenes. And the article contained the following:

Substituted (F, Cl, OH) diazanaphthalene derivatives were considered theor. to obtain information about their stabilities and aromaticities. The expected decrease of aromaticity of naphthalene itself by double aza substitution was compensated by substitution of one of the hydrogens of the system by an electroneg. atom. The position of the substituent is strongly effective on the aromaticity of the structure such that, the aromaticity is enhanced when the substituent is closer to the aza points. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Synthetic Route of 62163-09-1

The Article related to aromaticity diazanaphthalene, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.Synthetic Route of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On July 3, 2014, Masuda, Naoyuki; Miyamoto, Satoshi; Kikuchi, Shigetoshi; Samizu, Kiyohiro; Sato, Fumie; Shiina, Yasuhiro; Hamaguchi, Wataru; Seo, Tatsushi; Mihara, Takuma published a patent.Safety of 5-Chloroquinoxaline The title of the patent was Preparation of pyrazole compounds as inhibitors of phosphodiesterase 10A. And the patent contained the following:

The title compounds [I; ring A = (un)substituted aromatic heterocyclyl; B = phenylene, pyridinediyl, thiophenediyl, or CC each optionally substituted by ≥1 group selected from C1-6 alkyl, halo, C1-6 alkyloxy, and each (un)substituted cycloalkyl and nonaromatic heterocyclyl; n = 0, 1; L1 = C1-6 alkylene, C1-6 alkylene-T, T-C1-6 alkylene; provided that when n = 0, L1 = trimethylene-T or tetramethylene-T; T = O, S, NH, N(C1-6 alkyl); X = CR0, N; R0 = H, C1-6 alkyl; R1 = H or C1-6 alkyl optionally substituted by ≥1 group selected from halo, HO, C1-6 alkyloxy, cyano, CO2H, and CO2-C1-6 alkyl; ring E = each (un)substituted cycloalkyl, aryl, aromatic heterocyclyl, or nonaromatic heterocyclyl] or salts thereof were prepared These pyrazole compounds have phosphodiesterase 10A (PDE10A)-inhibitory actions, and can be used for the prevention of and/or as therapeutic agents for schizophrenia, anxiety, Huntington’s disease, drug dependence, and/or Alzheimer’s disease. Thus, amidation of 4-[[[1-methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]oxy]methyl]benzoic acid with 1,2-phenylenediamine using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole, and Et4N in DMF at room temperature for 1 h followed by cyclization of the resulting amide under heating at 90° for 12 h and salt formation with HCl in EtOAc gave 2-[4-[[[1-methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]oxy]methyl]phenyl]-1H-benzimidazole (II) dihydrochloride. II.2HCl and compound (III).2HCl showed IC50 of 17 and 0.4 nM, resp., against human PDE10A. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Safety of 5-Chloroquinoxaline

The Article related to pyrazole preparation inhibitor phosphodiesterase 10a pde10a, schizophrenia anxiety huntington disease prevention treatment pyrazole preparation, drug dependence alzheimer disease prevention treatment pyrazole preparation, pyridinylpyrazolyloxymethylphenybenzimidazole preparation inhibitor phosphodiesterase 10a and other aspects.Safety of 5-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On April 30, 1989, Lewanowicz, A.; Lipinski, J.; Ruziewicz, Z.; Szymczak, A.; Szynkarczuk, J. published an article.Category: quinoxaline The title of the article was Position-dependent effects of internal heavy atoms on highly resolved electronic spectra and luminescence properties of some quinoxalines substituted at the homocyclic ring. And the article contained the following:

Highly resolved phosphorescence and S1(n,π*)  S0 phosphorescence excitation spectra and some photophys. properties of monohaloquinoxalines (I; R = H, R1 = Br, Cl; R = Br, Cl, R1 = H) are compared. Exptl. data are supplemented by theor. study of the electronic structures, performed with the use of a modified INDO CI method. Insensitivity of phosphorescence lifetimes of I to the nature of the solvent is discussed. The substituent position-dependent T1 state energy is recognized as the main factor differentiating the vibronic structure of the phosphorescence spectra and the luminescence properties of I. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Category: quinoxaline

The Article related to substituent effect luminescence haloquinoxaline, quinoxaline halo electronic spectra, electronic spectra haloquinoxaline substituent effect, phosphorescence spectra haloquinoxaline substituent effect, heavy atom effect haloquinoxaline luminescence, indo ci haloquinoxaline electronic structure, solvent effect phosphorescence lifetime haloquinoxaline and other aspects.Category: quinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On November 23, 2017, Teng, Che-Ming; Liou, Jing-Ping; Pan, Shiow-Lin; Yang, Chia-Ron published a patent.Synthetic Route of 62163-09-1 The title of the patent was Preparation of benzohydroxamic acid and (E)-3-phenylpropenohydroxamic acid derivatives as selective histone deacetylase 6 inhibitors and use thereof. And the patent contained the following:

The hydroxamic acid compounds of formula I [R1, R2, R3, R4 = independently H, halo, cyano, amino, hydroxy, COR, CO2R, CONR’R”, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 alkoxy, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; or R3 and R4, together with the C in CR3R4, form C(:O), C(:S), or C(=NH); R, R’, R” = independently H, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; W = bicyclic aryl or bicyclic heteroaryl; X = CR5R6, O, S, or NR7; R5, R6, R7 = independently H, COR, CO2R, CONR’R”, C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, C2-5 alkoxy, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; Y = arylene or heteroarylene; Z = a bond, methylene, or ethylene; m, n = independently 0 or 1; wherein each of the C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, C2-5 alkoxy, C1-8 alkyl, C2-5 alkenyl, C2-8 alkynyl, C1-8 alkoxy, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylene, and heteroarylene are unsubstituted or substituted with halo, cyano, amino, hydroxy, nitro, sulfhydryl, C1-5 alkyl, C2-5 alkoxy, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl] or pharmaceutically acceptable salts thereof are prepared The compounds I or pharmaceutically acceptable salts thereof are selective inhibitors of histone deacetylase 6 (HDAC6) over other histone deacetylases including HDAC3, HDAC4, HDAC5, HDAC7, HDAC8, HDAC9, and sirtuin-1. A pharmaceutical composition containing the compound I or pharmaceutically acceptable salt thereof and a method of using the compounds I for treating a condition associated with histone deacetylase 6 such as cancer or neurodegenerative disorder are also disclosed. Thus, reductive amination of Me terephthalaldehydate with 5-aminoquinoline and NaBH(OAc)3 in the presence of AcOH at room temperature gave Me 4-[(quinolin-5-ylamino)methyl]benzoate which was condensed with hydroxylamine in the presence of NaOH in methanol at room temperature to give N-hydroxy-4-[(quinolin-5-ylamino)methyl]benzamide (II). II showed IC50 of 2.65 μM and 2.73 nM against histone deacetylase 1 (HDAC1) and histone deacetylase 6 (HDAC6), resp., compared to IC50 of 9.5 μM and 26.16 nM, resp., for tubastatin A. II showed GI50 of 3.28±0.11 μM and 5.53±0.24 nM against the proliferation of prostate cancer (PC-3) and lung (A549) cancer cell line, resp., compared to GI50 of 48.19±0.43 μM and 52.2±1.28 nM, resp., for tubastatin A. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Synthetic Route of 62163-09-1

The Article related to benzohydroxamic acid preparation selective histone deacetylase 6 inhibitor, cancer neurodegenerative disease treatment benzohydroxamic acid phenylpropenohydroxamic acid preparation, phenylpropenohydroxamic acid preparation selective histone deacetylase 6 inhibitor, hydroxyphenylacrylamide hydroxybenzamide preparation histone deacetylase 6 inhibitor and other aspects.Synthetic Route of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On October 4, 2012, Masuda, Naoyuki; Miyamoto, Satoshi; Kikuchi, Shigetoshi; Samizu, Kiyohiro; Sato, Fumie; Shiina, Yasuhiro; Hamaguchi, Wataru; Seo, Ryushi; Mihara, Takuma published a patent.Quality Control of 5-Chloroquinoxaline The title of the patent was Preparation of pyrazole compounds as inhibitors of phosphodiesterase 10A. And the patent contained the following:

The title compounds [I; ring A = (un)substituted aromatic heterocyclyl; B = phenylene, pyridinediyl, thiophenediyl, or CC each optionally substituted by ≥1 group selected from C1-6 alkyl, halo, C1-6 alkyloxy, and each (un)substituted cycloalkyl and nonaromatic heterocyclyl; n = 0, 1; L1 = C1-6 alkylene, C1-6 alkylene-T, T-C1-6 alkylene; provided that when n = 0, L1 = trimethylene-T or tetramethylene-T; T = O, S, NH, N(C1-6 alkyl); X = CR0, N; R0 = H, C1-6 alkyl; R1 = H or C1-6 alkyl optionally substituted by ≥1 group selected from halo, HO, C1-6 alkyloxy, cyano, CO2H, and CO2-C1-6 alkyl; ring E = each (un)substituted cycloalkyl, aryl, aromatic heterocyclyl, or nonaromatic heterocyclyl] or salts thereof were prepared These pyrazole compounds have phosphodiesterase 10A (PDE10A)-inhibitory actions, and can be used for the prevention of and/or as therapeutic agents for schizophrenia, anxiety, Huntington’s disease, drug dependence, and/or Alzheimer’s disease. Thus, amidation of 4-[[[1-methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]oxy]methyl]benzoic acid with 1,2-phenylenediamine using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-hydroxybenzotriazole, and Et4N in DMF at room temperature for 1 h followed by cyclization of the resulting amide under heating at 90° for 12 h and salt formation with HCl in EtOAc gave 2-[4-[[[1-methyl-4-(pyridin-4-yl)-1H-pyrazol-3-yl]oxy]methyl]phenyl]-1H-benzimidazole (II) dihydrochloride. II.2HCl and compound (III).2HCl showed IC50 of 17 and 0.4 nM, resp., against human PDE10A. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Quality Control of 5-Chloroquinoxaline

The Article related to pyrazole preparation inhibitor phosphodiesterase 10a pde10a, schizophrenia anxiety huntington disease prevention treatment pyrazole preparation, drug dependence alzheimer disease prevention treatment pyrazole preparation, pyridinylpyrazolyloxymethylphenybenzimidazole preparation inhibitor phosphodiesterase 10a and other aspects.Quality Control of 5-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On February 28, 1982, McNab, Hamish published an article.Application In Synthesis of 5-Chloroquinoxaline The title of the article was Carbon-13 nuclear magnetic resonance spectra of quinoxaline derivatives. And the article contained the following:

I (R = H, 5-Me, 5-Cl, 5-OMe, 6-Me; 5,6-Me2; R1 = H, 2-Me, 2-Cl, 2-OMe; 2,3-Me2) are prepared by the cyclocondensation of a phenylenediamine with an α-oxoaldehyde or an α,β-diketone; their 13C NMR are assigned by a first order anal. 2,3-(H2N)2C6H3Me was treated with OHCCHO and NaHSO3 in H2O to give I (R = 5-Me, R1 = H). The 13C-H coupling constants are reported for some I. Acceptable additivity of substituent effects is found within the quinoxaline series. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Application In Synthesis of 5-Chloroquinoxaline

The Article related to quinoxaline preparation carbon 13 nmr, glyoxal cyclocondensation aminotoluene, Physical Organic Chemistry: Resonance Spectra (Electron Spin, Nuclear Magnetic and Fourier Transform Nuclear Magnetic, Quadrupole, etc.) and other aspects.Application In Synthesis of 5-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Verbeek, J.; Berends, W.; Van Beek, H. C. A. published an article in 1976, the title of the article was Photochemical hydroxylation of quinoxalines.Category: quinoxaline And the article contains the following content:

Irradiation of quinoxaline (I) in acidic aqueous solution under anaerobic conditions gave 5-hydroxyquinoxaline (II) and the 1,4-dihydroquinoxaline radical cation (III). III was characterized by ESR spectroscopy. Under aerobic conditions II is the only irradiation product formed. The effect of substituents attached to the benzene nucleus of I is analyzed. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Category: quinoxaline

The Article related to photochem hydroxylation quinoxaline, esr dihydroquinoxaline radial cation, Physical Organic Chemistry: Photo- and Irradiation-Induced Reactions, Free Radical-Induced Reactions, Free Radical Reactions and other aspects.Category: quinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On May 31, 2010, Mohajeri, Afshan; Shahamirian, Mozhgan published an article.Name: 5-Chloroquinoxaline The title of the article was Substituent effect on local aromaticity in mono and di-substituted heterocyclic analogs of naphthalene. And the article contained the following:

A quant. study on local aromaticity has been performed on a series of mono- and di-substituted biheterocycles (quinoline, isoquinoline, quinoxaline, quinazoline). Three electronically based indexes (PDI, ATI, and FLU) have been employed to investigate the substituent effect on the π-electron delocalization in both heterocycle and benzenoid rings. Three typical substituents (Cl, OCH3, and CN) with different inductive and resonance power have been selected. Generally, substituent causes a reduction in aromaticity irresp. of whether it is electron attracting or electron donating. It is shown that the maximum aromaticity exhibits a similar trend of Cl > CN > OCH3 for all the studied rings. Moreover, it is found that the substituent situation with respect to the heteroatom has a significant influence on the aromaticity. It results from our study that in di-substituted derivatives, irresp. of whether the two substituents form a meta or para isomer, they preferably choose the position which leads to the maximum aromaticity character. Copyright © 2009 John Wiley & Sons, Ltd. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Name: 5-Chloroquinoxaline

The Article related to substituent effect local aromaticity substituted heterocyclic naphthalene analog, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.Name: 5-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider