Tag: M.W=150-200

Fisher, George H.; Schultz, Harry P. published the artcile< Quinoxaline studies. XXII. Tosylation and chiralities of 2-substituted 1,2,3,4-tetrahydroquinoxalines>, Safety of Quinoxaline-2-carboxamide, the main research area is tetrahydroquinoxaline tosylation chirality; quinoxaline tetrahydes tosylation chirality.

Tosylation of several 2-R-substituted-1,2,3,4-tetrahydroquinoxalines (I, (R = Me, CH2Oh, CONH2, CO2H, or CO2Et) gave exclusively N-monotosyl derivatives whose NMR spectra justified assignment of the tosyl group of the 1-N position. Support for this assignment was obtained by comparing the NMR spectra of unsubstituted and N-tosylated tetrahydroquinolines and tetrahydroquinaldines as model compounds The tosyl derivatives were then utilized to establish the C-2 chiralities of the various 2-substituted 1,2,3,4-tetrahydroquinoxalines according to the sequence (RS)-1,2,3,4-tetrahydro-2-quinoxalinecarboxamide, (R)-1,2,3,4-tetrahydro-2-quinoxalinecarboxamide, (R)-1-p-tolylsulfonyl-1,2,3,4-tetrahydro-2-quinoxalinecarboxamide, (R)-1-p-tolylsulfonyl-1,2,3,4-tetrahydro-2-quinoxalinecarboxylic acid, (R)-1-p-tolylsulfonyl-1,2,3,4-tetrahydroquinoxaline-2-hydroxymethylquine, and (S)-1-tolylsulfonyl-2-methyl-1,2,3,4-tetrahydroquinoxaline-the latter identical with the configurational standard prepared unequivocally from L-α-alanine.

Journal of Organic Chemistry published new progress about Chirality. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Safety of Quinoxaline-2-carboxamide.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Long, Xiangdong; Wang, Jia; Gao, Guang; Nie, Chao; Sun, Peng; Xi, Yongjie; Li, Fuwei published the artcile< Direct Oxidative Amination of the Methyl C-H Bond in N-Heterocycles over Metal-Free Mesoporous Carbon>, Synthetic Route of 5182-90-1, the main research area is amide heterocyclic preparation density functional theory kinetic study; heterocycle oxidative amination mesoporous carbon catalyst SAR.

Herein, direct and efficient oxidative amination of the Me C-H bond in a wide range of N-heterocycles such as 2-methylpyridine, 3-methylquinoline, 4-methylpyrimidine, etc. to access the corresponding amides RC(O)NH2 (R = pyridin-2-yl, quinolin-2-yl, 1-methyl-1H-imidazol-2-yl, etc.) over metal-free porous carbon is successfully developed. To understand the fundamental structure-activity relationships of carbon catalysts, the surface functional groups and the graphitization degree of porous carbon have been purposefully tailored through doping with nitrogen or phosphorus. The results of characterization, kinetic studies, liquid-phase adsorption experiments, and theor. calculations indicate that the high activity of the carbon catalyst is attributed to the synergistic effect of surface acidic functional groups (hydroxyl/carboxylic acid/phosphate) and more graphene edge structures exposed on the surface of carbon materials with a high graphitization degree, in which the role of acidic functional groups is to adsorb the substrate mol. and the role of the graphene edge structure is to activate O2.

ACS Catalysis published new progress about Adsorption energy. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Synthetic Route of 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Makhloufi, A.; Baitiche, M.; Merbah, M.; Benachour, D. published the artcile< Synthesis of new quinoxaline derivatives>, Related Products of 89898-96-4, the main research area is hydroxyquinoxaline alkyl aminoalkyl halide alkylation; quinoxaline derivative preparation.

New quinoxaline derivatives were prepared by the reaction of 2-hydroxyquinoxaline (I) and alkyl or alkylaminoalkyl halides in DMF using potassium carbonate as a base. The hydroxyl group was readily converted into a thiol function by treatment with phosphorus pentasulfide and/or Lawesson’s reagent in pyridine, and the subsequent alkylation of the thiol group was carried out under phase-transfer catalyst conditions. Chlorination of I was carried out with phosphorus oxychloride. Branching of alkylamino side chains to the 2-OH, 2-SH, and 2-Cl quinoxalines resulted in the synthesis of several compounds Synthesis and alkylation of 2-hydroxy 7-nitroquinoxaline were also reported.

Synthetic Communications published new progress about Alkylation. 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, Related Products of 89898-96-4.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Mohajeri, Afshan; Shahamirian, Mozhgan published the artcile< Substituent effect on local aromaticity in mono and di-substituted heterocyclic analogs of naphthalene>, Computed Properties of 23088-24-6, the main research area is substituent effect local aromaticity substituted heterocyclic naphthalene analog.

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.

Journal of Physical Organic Chemistry published new progress about Aromaticity. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Computed Properties of 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Hazeldine, Stuart T.; Polin, Lisa; Kushner, Juiwanna; Paluch, Jennifer; White, Kathryn; Edelstein, Matthew; Palomino, Eduardo; Corbett, Thomas H.; Horwitz, Jerome P. published the artcile< Design, Synthesis, and Biological Evaluation of Analogues of the Antitumor Agent, 2-{4-[(7-Chloro-2-quinoxalinyl)oxy]phenoxy}propionic Acid (XK469)>, COA of Formula: C8H5N3O3, the main research area is chloroquinoxalinyloxyphenoxypropionic acid structure antitumor; quinoxalinyloxyphenoxypropionic acid antitumor preparation.

2-{4-[(7-Chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid (XK469) I is among the most highly and broadly active antitumor agents to have been evaluated and scheduled to enter clin. trials in 2001. The mechanism or mechanisms of action of I remain to be elaborated. Accordingly, an effort was initiated to establish a pharmacophore hypothesis to delineate the requirements of the active site, via a comprehensive program of synthesis of analogs of I and evaluation of the effects of structural modification(s) on solid tumor activity. The strategy formulated chose to dissect the two-dimensional parent structure into three regions: I, ring A of quinoxaline; II, the hydroquinone connector linkage; and III, the lactic acid moiety-to determine the resultant in vitro and in vivo effects of chem. alterations in each region. Neither the A-ring unsubstituted nor the B-ring 3-chloro-regioisomer of I showed antitumor activity. The modulating antitumor effect(s) of substituents of differing electronegativities, located at the several sites comprising the A-ring of region I, were next ascertained. Thus, a halogen substituent, located at the 7-position of a 2-{4-[(2-quinoxalinyl)oxy]phenoxy}propionic acid, generated the most highly and broadly active antitumor agents. A Me, methoxy, or an azido substituent at this site generated a much less active structure, whereas 5-, 6-, 8-chloro-, 6-, 7-nitro, and 7-amino derivatives all proved to be essentially inactive. When the connector linkage (region II) of I was changed from that of a hydroquinone to either a resorcinol or a catechol derivative, all antitumor activity was lost. Of the carboxylic acid derivatives of I (region III), i.e., CONH2, CONHMe, CONMe2, CONHOH, CONHNH2, CN, or CN4H (tetrazole), only the monomethyl- and N,N-dimethylamides proved to be active.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, COA of Formula: C8H5N3O3.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Zhang, Zhongxing; Yin, Zhiwei; Kadow, John F.; Meanwell, Nicholas A.; Wang, Tao published the artcile< Azole-N-acetonitriles as carbonyl synthons: A one-pot preparation of heteroaryl amides from halides>, Reference of 5182-90-1, the main research area is heteroaryl amide preparation; halo heterocycle reaction azole acetonitrile oxidation amine displacement.

Azole-N-acetonitrile derivatives were utilized as synthons for an ambident carbonyl moiety via a strategy relying upon sequential base-mediated SNAr substitution of a 2-halo heterocycle, in situ oxidation, and amine displacement. This strategy allows prompt and efficient synthesis of N-containing heteroaryl amides directly from the corresponding halides via a one-pot process. E.g., reaction of 2-halo heterocycle I (R = Cl) with azole-N-acetonitrile derivative II, followed by reaction with Me2NH and oxidation with peracetic acid, gave 69% heteroaryl amide I (R = NMe2).

Synlett published new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation) (heteroaryl). 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Reference of 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Ma, Xuexiang; Zhao, Xia; Zhu, Rongxiu; Zhang, Dongju published the artcile< Computational Study on Why and How of Nonconventional meta-C-H Arylation of Electron-Rich Arenes via Pd/Quinoxaline-Based Ligand/Norbornene Cooperative Catalysis>, Recommanded Product: 6-Quinoxalinecarbonitrile, the main research area is electron rich arene arylation palladium quinoxaline norbornene cooperative catalysis.

By performing d. functional theory (DFT) calculation, this work aims at understanding the nonconventional meta-C-H arylation reaction of electron-rich arenes with aryl iodide via a Pd/quinoxaline-based ligand/norbornene cooperative catalysis. The reaction is indicated to be initiated either from the ortho-C-H carbopalladation to give the meta-monoarylation product via a sequence of subsequent steps, including norbornene insertion, meta-C-H activation, oxidative addition, and reductive elimination via the Pd(II)/Pd(IV)/Pd(II) redox cycle, norbornene extrusion, and protodepalladation, or from the para-C-H carbopalladation to form the meta-diarylation product via two sequential arylation processes following similar mechanisms. The initial carbopalladation process promoted by the ligand is characterized as the rate-determining step of the reaction. The calculated mechanism shows the distinct role of the norbornene as a transient mediator that enables the final C-H arylation at the same meta-position wherever the initial carbopalladation occurs at either ortho- or para-position. The Pd/ligand/norbornene cooperative catalysis is essential for achieving the exclusive meta-selectivity of the C-H arylation of electron-rich arenes.

Journal of Organic Chemistry published new progress about Arylation catalysts. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Recommanded Product: 6-Quinoxalinecarbonitrile.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Wakelin, Laurence P. G.; Waring, Michael J. published the artcile< The binding of echinomycin to deoxyribonucleic acid>, Product Details of C9H7N3O, the main research area is DNA echinomycin binding.

Association constants for the binding of echinomycin (I) [512-64-1] to 9 double-helical DNA species from different sources varied by a factor of approx. 10 but were not simply related to the gross base composition The interaction of I with DNA was ionic strength dependent and the enthalpy of interaction was approx. -13 kJ/mole. I interacted strongly with some synthetic polydeoxynucleotides, having the highest affinity for polymers rich in deoxyguanine and deoxycytosine nucleotides. I altered the supercoiling of closed circular duplex bacteriophage PM2 DNA in the same way as that of intercalating drugs. At low ionic strength (0.01M), the interaction was bifunctional, but at higher ionic strength (0.5M) the intercalation became more monofunctional. Quinoxaline-2-carboxamide [5182-90-1] and Bayer 7602 [13988-23-3] showed only weak interactions with DNA, indicating that the peptide portion of I is important in determining the strength and specificity of the interaction.

Biochemical Journal published new progress about DNA Role: FORM (Formation, Nonpreparative). 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Product Details of C9H7N3O.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Seitz, Lainne E.; Suling, William J.; Reynolds, Robert C. published the artcile< Synthesis and Antimycobacterial Activity of Pyrazine and Quinoxaline Derivatives>, Related Products of 5182-90-1, the main research area is benzyl pyrazinecarboxylate preparation antimycobacterial activity; quinoxalinecarboxylate benzyl preparation antimycobacterial activity.

A series of pyrazine and quinoxaline derivatives have been synthesized, and their activity against M. tuberculosis (Mtb) and Mycobacterium avium (MAC) are reported. The 4-acetoxybenzyl ester of pyrazinoic acid (I) and 4′-acetoxybenzyl 2-quinoxalinecarboxylate (II) showed excellent activity against Mtb (MIC ranges of less than 1-6.25 μg/mL) but only modest activity against MAC (MICs of 4-32 μg/mL).

Journal of Medicinal Chemistry published new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Related Products of 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Seitz, Lainne E.; Suling, William J.; Reynolds, Robert C. published the artcile< Synthesis and Antimycobacterial Activity of Pyrazine and Quinoxaline Derivatives>, Electric Literature of 5182-90-1, the main research area is benzyl pyrazinecarboxylate preparation antimycobacterial activity; quinoxalinecarboxylate benzyl preparation antimycobacterial activity.

A series of pyrazine and quinoxaline derivatives have been synthesized, and their activity against M. tuberculosis (Mtb) and Mycobacterium avium (MAC) are reported. The 4-acetoxybenzyl ester of pyrazinoic acid (I) and 4′-acetoxybenzyl 2-quinoxalinecarboxylate (II) showed excellent activity against Mtb (MIC ranges of less than 1-6.25 μg/mL) but only modest activity against MAC (MICs of 4-32 μg/mL).

Journal of Medicinal Chemistrypublished new progress about Aralkyl alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Electric Literature of 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider