Category: quinoxaline

On July 1, 2016, Huang, Wen-Xue; Liu, Lian-Jin; Wu, Bo; Feng, Guang-Shou; Wang, Baomin; Zhou, Yong-Gui published an article.Safety of 5,6,7,8-Tetrahydroquinoxaline The title of the article was Synthesis of Chiral Piperazines via Hydrogenation of Pyrazines Activated by Alkyl Halides. And the article contained the following:

A facile method has been developed for the synthesis of chiral piperazines through Ir-catalyzed hydrogenation of pyrazines activated by alkyl halides, giving a wide range of chiral piperazines including 3-substituted as well as 2,3- and 3,5-disubstituted ones with up to 96% ee. The high enantioselectivity, easy scalability, and concise drug synthesis demonstrate the practical utility. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Safety of 5,6,7,8-Tetrahydroquinoxaline

The Article related to pyrazine alkyl halide iridium chiral ligand hydrogenation catalyst, piperazine stereoselective preparation, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Safety of 5,6,7,8-Tetrahydroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On March 23, 2017, Soeberdt, Michael; Molenveld, Peter; Storcken, Roy P. M.; Bouzanne des Mazery, Renaud; Sterk, Geert Jan; Autar, Reshma; Bolster, Marjon G.; Wagner, Clemens; Aerts, Sebastianus N. H.; van Holst, Frank R.; Wegert, Anita; Tangherlini, Giovanni; Frehland, Bastian; Schepmann, Dirk; Metze, Dieter; Lotts, Tobias; Knie, Ulrich; Lin, Kun-Yuan; Huang, Tai-Yu; Lai, Chih-Ching; Staender, Sonja; Wuensch, Bernhard; Abels, Christoph published an article.Quality Control of 5,6,7,8-Tetrahydroquinoxaline The title of the article was Design and Synthesis of Enantiomerically Pure Decahydroquinoxalines as Potent and Selective κ-Opioid Receptor Agonists with Anti-Inflammatory Activity in Vivo. And the article contained the following:

In order to develop novel κ agonists restricted to the periphery, a diastereo- and enantioselective synthesis of (4aR,5S,8aS)-configured decahydroquinoxalines was developed. Physicochem. and pharmacol. properties were fine-tuned by structural modifications in the arylacetamide and amine part of the pharmacophore as well as in the amine part outside the pharmacophore. The decahydroquinoxalines show single-digit nanomolar to subnanomolar κ-opioid receptor affinity, full κ agonistic activity in the [35S]GTPγS assay, and high selectivity over μ, δ, σ1, and σ2 receptors as well as the PCP binding site of the NMDA receptor. Several analogs were selective for the periphery. The anti-inflammatory activity of decahydroquinoxalines after topical application was investigated in two mouse models of dermatitis. The methanesulfonamide I containing the (S)-configured hydroxypyrrolidine ring was identified as potent (Ki = 0.63 nM) and highly selective, κ agonist (EC50 = 1.8 nM) selective for the periphery with dose-dependent anti-inflammatory activity in acute and chronic skin inflammation. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Quality Control of 5,6,7,8-Tetrahydroquinoxaline

The Article related to decahydroquinoxaline stereoselective preparation opioid receptor agonistic antiinflammatory activity, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Quality Control of 5,6,7,8-Tetrahydroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On September 28, 2020, Gong, Yu; Li, Zhi-Hua; Yan, Xiaodong; Wang, Ya-Qin; Zhao, Chen-Yang; Han, Wang-Kang; Hu, Qing-Tao; Lu, Hui-Shu; Gu, Zhi-Guo published an article.Application of 34413-35-9 The title of the article was Bivariate Metal-Organic Frameworks with Tunable Spin-Crossover Properties. And the article contained the following:

In this work, pyrazine (A), aminopyrazine (B), quinoxaline (C), and 5,6,7,8-tetrahydroquinoxaline (D) have been screened out among a large number of pyrazine derivatives to construct Hofmann-type metal-organic frameworks (MOFs) Fe(L)[M(CN)4] (M=Pt, Pd) with similar 3D pillared-layer structures. X-ray single-crystal diffraction reveals that the alternate linkage between M and FeII ions through cyano bridges forms the 2D extended metal cyanide sheets, and ligands A-D acted as vertical columns to connect the 2D sheets to give 3D pillared-layer structures. Subsequently, a series of bivariate MOFs were constructed by pairwise combination of the four ligands A-D, which were confirmed by 1H NMR, PXRD, FTIR, and Raman spectroscopy. The results demonstrated that ligand size and crystallization rate play a dominant role in constructing bivariate Hofmann-type MOFs. More importantly, the spin-crossover (SCO) properties of the bivariate MOFs can be finely tuned by adjusting the proportion of the two pillared ligands in the 3D Hofmann-type structures. Remarkably, the spin transition temperatures, Tc↑ and Tc↓ of Fe(A)x(B)1-x[Pt(CN)4] (x=0 to 1) can be adjusted from 239 to 254 K and from 248 to 284 K, resp. Meanwhile, the width of the hysteresis loops can be widened from 9 to 30 K. Changing Pt to Pd, the hysteresis loops of Fe(A)x(B)1-x[Pd(CN)4] can be tuned from 9 (Tc↑=215 K, Tc↓=206 K) to 24 K (Tc↑=300 K, Tc↓=276 K). This research provides wider implications in the development of advanced bistable materials, especially in precisely regulating SCO properties. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Application of 34413-35-9

The Article related to iron pyrazine quinoxaline platinum palladium cyano mof preparation, spin crossover iron pyrazine quinoxaline platinum palladium cyano mof, thermal stability iron pyrazine quinoxaline platinum palladium cyano mof, crystal structure iron pyrazine quinoxaline platinum palladium cyano mof, hofmann, bivariate, hysteresis loops, metal-organic frameworks, spin-crossover and other aspects.Application of 34413-35-9

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 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 August 17, 2011, Trost, Barry M.; Thaisrivongs, David A.; Hartwig, Jan published an article.Electric Literature of 34413-35-9 The title of the article was Palladium-Catalyzed Asymmetric Allylic Alkylations of Polynitrogen-Containing Aromatic Heterocycles. And the article contained the following:

Nonracemic cyclohexenylmethyl- and cyclopentenylmethyl-substituted nitrogen heterocycles such as I are prepared in 44-93% yields and in 75->99% ee by enantioselective allylic alkylation reactions of cyclohexenyl and cyclopentenyl trimethylbenzoates with methyl-substituted nitrogen heterocycles such as 2-methylpyrazine in the presence of bis(allylpalladium chloride) and a nonracemic dibenzamidodibenzobicyclooctane ligand. Methylated nitrogen-containing aromatic heterocycles such as 2-methylpyrazine, 2-methylpyrimidine, 3-methyl-6-phenylpyridazine, 2-methylquinoxaline, and 1-benzyl-2-methylbenzimidazole are effective reactants. 5,6,7,8-Tetrahydroquinoxaline also undergoes enantioselective allylic alkylation with a cyclohexenyl trimethylbenzoate to give cyclohexenyl tetrahydroquinoxaline II in 99% yield, >99% ee, and in 81:19 diastereoselectivity. The mesityl ester, whose steric bulk prevents competitive deacylation of the electrophile from “hard” nucleophiles, is introduced as a new leaving group in allylic alkylation chem. In contrast to previous studies of enantioselective allylic alkylation reactions with pyridine-based substrates, no precomplexation with a Lewis acid is required before deprotonation of the nucleophiles with LiHMDS, underscoring the relative acidity of these electron-deficient nucleophiles. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Electric Literature of 34413-35-9

The Article related to cyclohexenylmethyl nitrogen heterocycle enantioselective preparation, enantioselective allylic alkylation cyclohexenyl cyclopentenyl mesityl ester nitrogen heterocycle, trimethylbenzoate ester leaving group enantioselective allylic alkylation reaction and other aspects.Electric Literature of 34413-35-9

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On February 6, 2008, Zhu, Guang; Pang, Keliang; Parkin, Gerard published an article.Safety of 5,6,7,8-Tetrahydroquinoxaline The title of the article was New modes for coordination of aromatic heterocyclic nitrogen compounds to molybdenum: catalytic hydrogenation of quinoline, isoquinoline, and quinoxaline by Mo(PMe3)4H4. And the article contained the following:

The heterocyclic nitrogen compounds (NHetH), isoquinoline (iQH), quinoxaline (QoxH) and quinazoline (QazH), react with Mo(PMe3)6 to give (η2-NHet)Mo(PMe3)4H as a result of cleavage of the C-H bond adjacent to the nitrogen atom. The C-H bond cleavage is reversible, the excess of PMe3 yields the starting compounds back. Furthermore, at elevated temperatures (η2-NHet)Mo(PMe3)4H converts sequentially to isomers of (η6-C,N-NHetH)Mo(PMe3)3 in which the ligand coordinates via the heterocycle, and further, by a haptotropic shift, to (η6-C6-NHetH)Mo(PMe3)3 with coordination via the carbocyclic ring. Isomers of (η6-C,N-NHetH)Mo(PMe3)3 in which the heterocyclic ring coordinated to molybdenum may be hydrogenated, yielding the 1,2,3,4-tetrahydro-derivatives Thus, (η6-C5N-iQH)Mo(PMe3)3 and (η6-C4N2-QoxH)Mo(PMe3)3 react with H2 at 90° to give Mo(PMe3)4H4 and release 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydroquinoxaline, resp. Furthermore, Mo(PMe3)4H4 serves as a catalyst precursor for the hydrogenation of quinoline, isoquinoline, and quinoxaline to the corresponding 1,2,3,4-tetrahydro-heterocycles. The Mo(PMe3)4H4 is the first simple molybdenum complex to effect catalytic hydrogenation of these heterocyclic nitrogen compounds, a necessary step in hydrodenitrogenation. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Safety of 5,6,7,8-Tetrahydroquinoxaline

The Article related to molybdenum trimethylphosphine isoquinoline quinoxaline quinazoline complex preparation haptotropic rearrangement, hydrogenation partial isoquinoline quinoxaline quinazoline molybdenum trimethylphosphine complex and other aspects.Safety of 5,6,7,8-Tetrahydroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On August 31, 2014, Rana, Abhinandan; Kumar Jana, Swapan; Pal, Tanusri; Puschmann, Horst; Zangrando, Ennio; Dalai, Sudipta published an article.Name: 5,6,7,8-Tetrahydroquinoxaline The title of the article was Electrical conductivity and luminescence properties of two silver(I) coordination polymers with heterocyclic nitrogen ligands. And the article contained the following:

The synthesis and X-ray structural characterization of two novel silver(I) coordination polymers, [Ag(NO3)(quin)]n (1) and [Ag8(HL)2(H2O)4(mpyz)]·3H2O (2) are reported, where quin=5,6,7,8-tetrahydroquinoxaline, H6L=cyclohexane-1,2,3,4,5,6-hexacarboxylic acid and mpyz=2-Me pyrazine. The single crystal diffraction analyses showed that complex 1 is a 2D layered structure, while 2 presents a 3D polymeric architecture. In complex 2 the network is stabilized by argentophilic interactions and hydrogen bonding. Elec. conductivity of order 3 × 10-4 Scm-1 (1) and 1.6 × 10-4 Scm-1 (2) is measured on thin film specimen at room temperature The photoluminescence and thermal properties of the complexes have also been studied. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Name: 5,6,7,8-Tetrahydroquinoxaline

The Article related to silver tetrahydroquinoxaline cyclohexanehexacarboxylate methylpyrazine polymer elec conductivity luminescence, crystal structure silver tetrahydroquinoxaline cyclohexanehexacarboxylate methylpyrazine polymer and other aspects.Name: 5,6,7,8-Tetrahydroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider