Month: April 2022

Category: quinoxaline. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 1-(Bromomethyl)-4-ethylbenzene, is researched, Molecular C9H11Br, CAS is 57825-30-6, about Syntheses of cytotoxic novel arctigenin derivatives bearing halogen and alkyl groups on aromatic rings. Author is Yamauchi, Satoshi; Wukirsari, Tuti; Ochi, Yoshiaki; Nishiwaki, Hisashi; Nishi, Kosuke; Sugahara, Takuya; Akiyama, Koichi; Kishida, Taro.

The new lignano-9,9′-lactones (α,β-dibenzyl-γ-butyrolactone lignans), which showed the higher cytotoxicity than arctigenin, were synthesized. The well-known cytotoxic arctigenin showed activity against HL-60 cells (EC50 = 12 μM), however, it was inactive against HeLa cells (EC50 > 100 μM). The synthesized (3,4-dichloro, 2′-butoxy)-derivative and (3,4-dichloro, 4′-butyl)-derivative bearing the lignano-9,9′-lactone structures showed the EC50 values of 10 μM and 9.4 μM against HL-60 cells, resp. Against HeLa cells, the EC50 value of the (3,4-dichloro, 4′-butyl) derivative was 27 μM. By comparing the activities with the corresponding 9,9′-epoxy structure (THF compounds), the importance of the lactone structure of (3,4-dichloro, 2′-butoxy)-derivative and (3,4-dichloro, 4′-butyl)-derivative for the higher activities was shown. The substituents on the aromatic ring of the lignano-9,9′-lactones affected the cytotoxicity level, observing more than 10-fold difference.

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Quinoxaline | C8H6N2 | ChemSpider

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Vanadium. VII. Vanadium(IV) complexes of benzimidazoles and oxine N-oxide》. Authors are Dutta, R. L.; Lahiry, Subrata.The article about the compound:8-Hydroxyquinoline 1-oxidecas:1127-45-3,SMILESS:OC1=CC=CC2=CC=C[N+]([O-])=C12).COA of Formula: C9H7NO2. Through the article, more information about this compound (cas:1127-45-3) is conveyed.

cf. CA 60, 5057b. The following complexes were prepared and their magnetic moments determined at 30-5; VO(H2O)B2+, 1.63; VO(H2O)G2+, 1.50; VOG2, 1.59; VO(BC)2.H2O 1.60; and VO(Ox)2, 1.77 Bohr magnetons, where B is benzimidazole, G is 2-guanidino benzimidazole, BC is 2-benzimidazolecarboxylate.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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 Infrared and Raman spectra of 1,5-cyclooctadiene complexes of copper(I), silver(I), gold(I), and gold(III) and the nature of the gold compounds, published in 1973, which mentions a compound: 32717-95-6, Name is Chloro(1,5-cyclooctadiene)copper(I) dimer, Molecular C16H16Cl2Cu2, Recommanded Product: 32717-95-6.

There have been several recent reports on the spectra of C2H4 and 1,5-cyclooctadiene complexes of d8 metallic ions which have shown that 2 bands in the vibrational spectrum of the olefin are sensitive to the coordinated metal. A series of d10 ions were complexed to 1,5-cyclooctadiene and a shift was found having the order Au(I) ∼ Cu(I) > Ag(I). Three distinct compounds were also formed between 1,5-cyclooctadiene and Au(III) or Au(I) and their ir spectra and suggested structures are reported.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Quinoline-5,8-quinones》. Authors are Petrow, Vladimir; Sturgeon, Bennett.The article about the compound:8-Hydroxyquinoline 1-oxidecas:1127-45-3,SMILESS:OC1=CC=CC2=CC=C[N+]([O-])=C12).Quality Control of 8-Hydroxyquinoline 1-oxide. Through the article, more information about this compound (cas:1127-45-3) is conveyed.

5-Amino-8-hydroxyquinoline sulfate (1 g.) in 10 mL. 10% H2SO4 and Na2Cr2O7 in H2O, the whole extracted with CHCl3, the CHCl3 extracts concentrated and the residue diluted with petr. ether gave 0.35 g. quinoline-5,8-quinone, light yellow needles, m. 129° (decomposition). 8-Hydroxy-5-nitrosoquinaldine (5.8 g.) in 100 mL. H2O and 6.3 g. NaOH treated with about 13 g. Na2S2O4 (I) and neutralized with AcOH gave 5-amino-8-hydroxyquinaldine (II); II as above gave 2 g. quinaldine-5,8-quinone, yellow-green prisms, m. 145° (decomposition) (from EtOH-petr. ether). Similarly 8-hydroxy-5-nitroso-7-methylquinoline gave the amine (III), yellow prisms, m. 155° (decomposition) (from C6H6), and III gave the quinone, light yellow needles, m. 181-2° (from EtOH-petr. ether). A solution of PhN2Cl (from 7 g. PhNH2.HCl and 4 g. NaNO2) added during 20 min. at 0-3° to 8.5 g. 5-amino-O-methylquinoline in 50 mL. AcOH, 200 mL. H2O, and 25 g. AcONa gave 9 g. 5-amino-6-methyl-8-phenylazoquinoline-HCl (IV), red-brown plates, m. 216° (from EtOH-petr. ether). IV (12 g.), 60 cc. concentrated HCl, 50 mL. H2O, and 150 mL. EtOH refluxed 2.5 h. gave 7 g. HCl salt, m. 212° (from EtOH), of the 5-HO analog (V), fine red needles m. 177° (from EtOH). V (1.5 g.) in EtOH, Pd-C, and H gave 0.5 g. 8-amino-5-hydroxy-6-methylquinoline (VI), pale brown plates, m. 216° (from EtOH). VI gave 6-methylquinoline-5,8-quinone, yellow needles, m. 188° (from CHCl3-petr. ether). 2,6-Dimethylquinoline (3.0 g.) in 8,5 mL. cold concentrated H2SO4, treated with 1.5 mL. concentrated HNO3 in 2.0 mL. concentrated H2SO4 2 h. on the steam bath, and the whole poured into cold dilute aqueous NH3 gave 3.8 g. 2,6-dimethyl-5-nitroquinoline (VII), pale yellow prisms, m. 106° (from pert. ether). VII (2.5 g.), 25 mL. 80% EtOH, 1 mL. concentrated HCl, and 6 g. reduced Fe gave 2.0 g. 5-amino analog (VIII), green needles, m. 190° (from C6H6-petr. ether), and VIII as above gave 60% 2,6-dimethylquinoline-5,8-quinone (IX), yellow plates, m. 150°, also obtained via 5-amino-2,6-dimethyl-8-phenylazoquinoline-HCl, red plates with green reflex, m. 210°, and 5-hydroxy-2,6-dimethyl-8-phenylazoquinoline, dark red fluffy needles, m. 168° (from EtOH), and 8-amino-5-hydroxy-2,6-dimethylquinoline (X) (X was very sensitive to air oxidation and was used directly without purification). Finely powd. 8-hydroxy-5-nitrosoquinoline (3 g.) added to 9 mL. concentrated HNO3 and 6 mL. H2O and kept 1.25 h. at 17° gave a precipitate of 8-hydroxy-5-nitroquinoline-HNO3; the whole cooled to 0° made alk. with cold KOH solution, and the red K salt decomposed with AcOH gave 2.9 g. 8-hydroxy-5-nitroquinoline, yellow needles, m. 180° (from EtOH). Similarly, 8-hydroxy-5-nitrosoquinaldine gave 8-hydroxy-5-nitroquinaldine, silky yellow needles, m. 136° (from C6H6-petr. ether) (a small amount of 8-hydroxy-5,7-dinitroquinaldine, small yellow needles, m. above 300° was a byproduct). The following compounds were prepared by this general procedure: To 1 g. nitro compound in 300 mL. H2O and 0.9 g. KOH was added 1 mol. equivalent Br or iodine dissolved in KBr or KI, resp., and the whole stirred at room temperature 2 h. and acidified, giving 60-70% yield of the halogenated product (all derivatives recrystallized from EtOCH2CH2OH): 7-bromo-8-hydroxy-5-nitroquinoline (XI), red felted needles, m. 200°; 7-bromo-8-hydroxy-5-nitroquinaldine (XII), red plates, m. 265° (decomposition); and 8-hydroxy-7-iodo-5-nitroquinaldine (XIII), bright red plates, m. 244°. As above, with I, XI gave the amino compound (XIV), light brown needles, m. 184° (decomposition) (from EtOAc-petr. ether); XII gave the amino compound (XV), golden brown needles, m. 176° (decomposition); and XIII gave the amino compound (XVI), yellow needles, m. 162° (decomposition from Et2O-petr. ether). As above, with Na2Cr2O7 were prepared the following 5,8-quinones (all recrystallized from CHCl3-petr. ether): 7-bromoquinoline (from XIV), pale yellow needles, m. 182°; 7-bromoquinaldine (from XV), orange-yellow needles, m. 178°; 7-iodoquinoline (from XVI), unstable yellow-brown needles, m. 160° (decomposition); and 7-iodoquinaldine, yellow-brown needles, m. 160° (decomposition). 4-IC6H4NH2 (XVII) (42 g.), 70 g. dry glycerol, and 33 g. As2O5 heated to 120° 20 mL. concentrated H2SO4 added dropwise with stirring, and with the temperature kept at 120° the whole refluxed 4 h., 600 mL. H2O added, the mixture filtered, the filtrate made alk. with aqueous NH3, extracted with C6H6, the C6H6 extracts extracted with 6N HCl, the base liberated from the HCl extracts with NaOH, extracted with CHCl3 and the CHCl3 extracts concentrated and distilled gave 6-iodoquinoline (XVIII), b1 120° pale yellow prisms, m. 88° (from petr. ether). XVIII (1.5 g.), 4.5 mL. concentrated H2SO4, and 0.8 mL. concentrated HNO3 in 1 mL. concentrated H2SO4 heated 1 h. at 100° gave 1.5 g. 6-iodo-5-nitroquinoline, m. 163° (from C6H6). XVII (25 g.), 20 mL. concentrated HCl, and 20 mL. paraldehyde kept overnight, the whole refluxed 2 h., H2O added, the aqueous solution decanted from the resin (XIX), the XIX extracted twice with 2N HCl, the combined HCl solutions treated as above m the preparation of XVIII gave 5.9 g. 6-iodoquinaldine (XX), prisms, m. 112° (from petr. ether). As above XX gave 90% 6-iodo-5-nitroquinaldine (XXI), pale yellow needles, m. 146 ° (from EtOH). XXI (5 g.) and 25 g. PhNH2 heated 2 h. at 180°, AcONa solution added, the excess PhNH2 steam distilled, the residue extracted with C6H6, the C6H6 extracts percolated through Al2O3, and the C6H6 evaporated gave 6-anilino-5-nitroquinaldine, felted orange needles, m. 147-8° (from EtOH). XXI (2.5 g.), 7 g. reduced Fe, 20 mL. EtOH, and 5 drops concentrated HCl refluxed 2 h., the whole filtered, and the filtrate made alk. with aqueous NH3 gave 2 g. 5-amino-6-iodoquinaldine, golden plates, m. 206° (decomposition) (from C6H6-petr. ether). 8-Hydroxyquinoline (2 g.) in CHCl3 and 2 mol ethereal peroxyphthalic acid in Et2O kept overnight, the whole evaporated to dryness, and the residue triturated with aqueous NH3 gave 8-hydroxyquinoline N-oxide (XXII), golden yellow needles, m. 138°. XXII (3.2 g. in 400 mL. 0.2% NaOH and 5.1 g. iodine in KI gave 8-hydroxy-5(?)-iodoquinoline N-oxide, yellow needles, m. 169° (from C6H6). XXII (1.6 g.) in 10 mL. AcOH and 1 mL. concentrated HNO3 kept 1 h. at 20° gave a precipitate of the nitrate which, decomposed with KOH, yielded 8-hydroxy-5(?)-nitroquinoline N-oxide (XXIII), light brown powder, m. 217-18° (decomposition) (from alc.). XXIII and I as above gave the amine, orange-red needles, m. 213° (decomposition) (from C6H6). Quinoline-5,8-quinone (0.75 g.), 1.2 g. PhNH2, and 10 mL. EtOH refluxed 1 h. and the whole poured into dilute AcOH gave 6(7)-anilinoquinoline-5,8-quinone, scarlet needles, m. 213° (decomposition) (from C6H6petr. ether). 7-Bromoquinoline-5,8-quinone (0.1 g.), 0.053 g. PhNH2.HCl, 0.05 g. AcONa, and 5 mL. alc. refluxed 2 h., and the whole poured into H2O gave 0.1 g. 6-anilino-7-bromoquinoline-5,8-quinone, dark red prisms, m. 189° (decomposition). 8-Hydroxy-5-nitroquinoline (2 g.) in 20 mL. boiling EtOH with 2 mL. 36% HCHO and 2 mL. morpholine gave 2.3 g. 8-hydroxy-7-morpholinomethyl-5-nitroquinoline, yellow prisms (which rapidly discolor), m. 112° (decomposition).

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Quinoxaline – Wikipedia,
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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 Acid reaction and ionization constants of 8-hydroxyquinoline-N-oxide, published in 1969, which mentions a compound: 1127-45-3, Name is 8-Hydroxyquinoline 1-oxide, Molecular C9H7NO2, Application of 1127-45-3.

The constants for the acid reactions of 8-hydroxyquinoline-N-oxide were determined at 25° and M ionic strength. The 1st ionization constant for the cation of oxine-N-oxide, H2Q+, was 0.0486 ± 0.0004. The constant for the acid reaction for the 2nd ionization of the above compound was 176 kw ± 15, where kw is the ion product of water. This constant is for the ionization of oxine-N-oxide which produces H ions and a combination of basic forms including the anion and the Na salt. The 1st ionization constant was determined by potentiometric measurements. The 2nd ionization was studied by solvent extraction methods. The reagent was synthesized by a modified K. Ramaiah and V. R. Srinivasan (1962) procedure.

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Product Details of 221012-82-4. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine, is researched, Molecular C38H34N2O4P2, CAS is 221012-82-4, about Air-stable Ir-(P-Phos) complex for highly enantioselective hydrogenation of quinolines and their immobilization in poly(ethylene glycol) dimethyl ether (DMPEG). Author is Xu, Lijin; Lam, Kim Hung; Ji, Jianxin; Wu, Jing; Fan, Qing-Hua; Lo, Wai-Hung; Chan, Albert S. C..

An air-stable catalyst system Ir-(P-Phos) catalyst was found to be highly effective in the asym. hydrogenation of quinoline derivatives The catalyst immobilized in DMPEG was efficiently recovered and reused eight times, retaining reactivity and enantioselectivity.

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Quinoxaline – 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: 57825-30-6, is researched, SMILESS is CCC1=CC=C(CBr)C=C1, Molecular C9H11BrJournal, Article, Research Support, Non-U.S. Gov’t, European Journal of Medicinal Chemistry called Design, synthesis, and biological evaluation of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase, Author is Chai, Xiaoyun; Zhang, Jun; Hu, Honggang; Yu, Shichong; Sun, Qingyan; Dan, Zhigang; Jiang, Yuanying; Wu, Qiuye, the main research direction is triazole preparation cytochrome P 450 14 alpha demethylase inhibitor; mol modeling triazole cytochrome P 450 14 alpha demethylase.Electric Literature of C9H11Br.

Based on the results of computational docking to the active site of the cytochrome P 450 14α-demethylase (CYP51), a series of 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted-2-propanols I (R = H, 2-F, 2,4-Cl2, 4-MeO2C, PhO2C, etc.) as analogs of fluconazole were designed, synthesized, and evaluated as antifungal agents. The MIC80 values indicate that compounds I (R = H, 2-F, 4-Me, etc.) exhibited higher activity against nearly all fungi tested except Aspergillus fumigatus than fluconazole, while I (R = COOR1, R1 = Me, Et, iso-Pr, COOAr, etc.; Ar = Ph, 3-O2NC6H4, 4-ClC6H4, 2-MeO2CC6H4, etc.) showed no activity or only moderate activity against all fungi tested. Noticeably, the MIC value of I (R = H, 2-F, 4-Cl) is 64 times lower than that of fluconazole against Microsporum gypseum in vitro. And I (R = H, 2-F, CO2Et) showed 128 times higher activity (with the MIC80 value of 0.0039 μg/mL) than that of fluconazole against Candida albicans and also showed higher activity than that of the other pos. controls. Computational docking experiments indicated that the inhibition of CYP51 involves a coordination bond with iron of the heme group, the hydrophilic H-bonding region, the hydrophobic region, and the narrow hydrophobic cleft. In addition, the activity of the compounds would be enhanced when the side chains were shorter.

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Quinoxaline – Wikipedia,
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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Zhurnal Neorganicheskoi Khimii called Use of sulfur hexafluoride in the synthesis of anhydrous iron, nickel, and cobalt fluorides, Author is Opalovskii, A. A.; Labkov, E. U.; Zakhar’ev, Yu. V.; Kuchumova, L. Ya., which mentions a compound: 13940-83-5, SMILESS is [H]O[H].[H]O[H].[H]O[H].[H]O[H].[Ni+2].[F-].[F-], Molecular F2H8NiO4, Application In Synthesis of Nickel(ii)fluoridetetrahydrate.

DTA data indicate that SF6 reacts with Fe2O3, NiO, or Co2O3 at 550-600° to give FeF3, NiF2, or CoF2, resp. During the heating of FeF3.3H2O, NiF2.4H2O, and CoF2.3.7H2O in the presence of SF6 at 650°, the formation of the oxide is avoided and FeF3, NiF2, and CoF2 are obtained.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Grasa, Gabriela A.; Zanotti-Gerosa, Antonio; Hems, William P. published the article 《A chiral [(dipyridylphosphine)RuCl2(1,3-diphenylpropanediamine)] catalyst for the hydrogenation of aromatic ketones》. Keywords: hydrogenation transfer stereoselective ruthenium catalyst preparation ketone; phenylphosphine bipyridine ruthenium propanediamine preparation transfer hydrogenation catalyst; asym synthesis phenylphosphine bipyridine ruthenium propanediamine preparation.They researched the compound: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine( cas:221012-82-4 ).Name: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine. 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:221012-82-4) here.

The use of chiral (+)-(S,S)-1,3-Diphenyl-1,3-propanediamine in combination with Ru-Xyl-P-Phos, gave up to 95% ee in the hydrogenation of acetophenone. Thus, [(3R)-4,4′-bis[bis(3,5-dimethylphenyl)phosphine]-2,2′,6,6′-tetramethoxy-3,3′-bipyridine]dichloro[(1S,3S)-1,3-diphenyl-1,3-propanediamine]ruthenium was prepared and its catalytic activity and selectivity were compared with its corresponding stereoisomers.

I hope my short article helps more people learn about this compound((R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine)Name: (R)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine. Apart from the compound(221012-82-4), you can read my other articles to know other related compounds.

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Quinoxaline – Wikipedia,
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Yamamoto, Yasuo; Kawanishi, Eiji; Koga, Yuichi; Sakamaki, Shigeki; Sakamoto, Toshiaki; Ueta, Kiichiro; Matsushita, Yasuaki; Kuriyama, Chiaki; Tsuda-Tsukimoto, Minoru; Nomura, Sumihiro published the article 《N-glucosides as human sodium-dependent glucose co-transporter 2 (hSGLT2) inhibitors》. Keywords: urinary glucose amino glycoside preparation human hyperglycemia structure activity; amino glycoside preparation antidiabetic human SGLT2 inhibitor pharmacokinetic; Diabetes; Glucoside; N-glucoside; SGLT2; Sodium-dependent glucose cotransporter.They researched the compound: 1-(Bromomethyl)-4-ethylbenzene( cas:57825-30-6 ).Computed Properties of C9H11Br. 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:57825-30-6) here.

Inhibition of renal sodium-dependent glucose co-transporter 2 (SGLT2) increases urinary glucose excretion (UGE), and thus reduces blood glucose levels in hyperglycemia. A series of N-glucosides was synthesized for biol. evaluation as human SGLT2 (hSGLT2) inhibitors. Among these compounds, N-glucoside 9d possessing an indole core structure showed good in vitro activity (IC50 = 7.1 nM against hSGLT2). Furthermore, 9d exhibited favorable in vivo potency with regard to UGE in rats based on good pharmacokinetic profiles.

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Quinoxaline – Wikipedia,
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