Heterocyclic Building Blocks-quinoxaline

Lumma, William C. Jr.; Hartman, Richard D.; Saari, Walfred S.; Engelhardt, Edward L.; Lotti, Victor J.; Stone, Clement A. published the artcile< Piperazinylquinoxalines with central serotoninmimetic activity>, Category: quinoxaline, the main research area is serotoninmimetic piperazinylquinoxaline; serotoninin reuptake blocking quinoxaline; piperazinylquinoxaline; quinoxaline piperazinyl.

The piperazinylquinoxalines I (R = H, Ac, Me; R1 = H, OH (and the related ketone), CO2H; R2, R3 = H, Cl, NH2, CF3, SPh, OMe, F, etc.; m, n = 0, 1) were prepared by various methods. I were tested for selectivity in regards to serotonin reuptake blocking and serotoninmimetic activity. In general, introduction of a 6-substituent into I enhanced serotonin reuptake blocking activity and diminished serotoninmimetic activity. Unsubstituted I and I (R1 = OH) had primary serotoninmimetic activity.

Journal of Medicinal Chemistry published new progress about 6272-25-9. 6272-25-9 belongs to class quinoxaline, and the molecular formula is C8H4ClN3O2, Category: quinoxaline.

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)>, Category: quinoxaline, 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. 6272-25-9 belongs to class quinoxaline, and the molecular formula is C8H4ClN3O2, Category: quinoxaline.

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

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

Wozniak, Marian; Baranski, Andrzej; Nowak, Krystyna; Poradowska, Henryka published the artcile< Regioselectivity of the amination of some nitroquinoxalines by liquid ammonia/potassium permanganate>, SDS of cas: 89898-96-4, the main research area is regioselective amination nitroquinoxaline; quinoxaline nitro regioselective amination.

5- And 6-nitroquinoxalines and some of their derivatives are aminated in a liquid NH3 solution of KMnO4 to yield the corresponding 2- and/or 3- and/or 5-amino compounds Quantum-chem. calculations are made to explain the regioselectivity of the amination reactions.

Liebigs Annalen der Chemie published new progress about Amination, regioselective. 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, SDS of cas: 89898-96-4.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Senecal, Todd D.; Shu, Wei; Buchwald, Stephen L. published the artcile< A General, Practical Palladium-Catalyzed Cyanation of (Hetero)Aryl Chlorides and Bromides>, SDS of cas: 23088-24-6, the main research area is heteroaryl aryl cyanide preparation; palladium catalyst cyanation heteroaryl aryl chloride bromide; cross-coupling; cyanides; heterocycles; homogeneous catalysis; palladium.

The authors have disclosed a general method for the cyanation of (hetero)aryl chlorides and bromides. The authors use a palladium-catalyzed cyanation system that (1) is applicable to aryl chlorides at low to moderate catalyst loadings; (2) works well with a wide range of heterocyclic halides, including in many cases five-membered heterocycles bearing free NH groups; and (3) is complete in one hour at ≤ 100°. The use of a nontoxic cyanide source in conjunction with wide functional-group tolerance and fast reaction times make this method particularly convenient to synthetic chemists.

Angewandte Chemie, International Edition published new progress about Aromatic nitriles Role: SPN (Synthetic Preparation), PREP (Preparation). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, SDS of cas: 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Senecal, Todd D.; Shu, Wei; Buchwald, Stephen L. published the artcile< A General, Practical Palladium-Catalyzed Cyanation of (Hetero)Aryl Chlorides and Bromides>, Reference of 23088-24-6, the main research area is heteroaryl aryl cyanide preparation; palladium catalyst cyanation heteroaryl aryl chloride bromide; cross-coupling; cyanides; heterocycles; homogeneous catalysis; palladium.

The authors have disclosed a general method for the cyanation of (hetero)aryl chlorides and bromides. The authors use a palladium-catalyzed cyanation system that (1) is applicable to aryl chlorides at low to moderate catalyst loadings; (2) works well with a wide range of heterocyclic halides, including in many cases five-membered heterocycles bearing free NH groups; and (3) is complete in one hour at ≤ 100°. The use of a nontoxic cyanide source in conjunction with wide functional-group tolerance and fast reaction times make this method particularly convenient to synthetic chemists.

Angewandte Chemie, International Editionpublished new progress about Aromatic nitriles Role: SPN (Synthetic Preparation), PREP (Preparation). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Reference of 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

do Amaral, Daniel N.; Alves, Fernando R. de Sa; Barreiro, Eliezer J.; Laufer, Stefan A.; Lima, Lidia M. published the artcile< Multi-gram preparation of 7-nitroquinoxalin-2-amine>, SDS of cas: 89898-96-4, the main research area is nitro quinoxalinamine regioselective preparation.

Methodologies to obtain quinoxaline compounds regioselectively were rarely reported in literature, thus regioselective and multi-gram methodologies to obtain these derivatives were desirable to explore the entire potential of these scaffolds for academic and/or com. application. A facile and multi-gram methodol. was described to obtain compound 7-nitroquinoxalin-2-amine I using o-phenylenediamine, a cheap and readily available reactant, as starting material in a five-step procedure in good yields and high purity without further purification such as crystallization or column chromatog.

Journal of the Brazilian Chemical Societypublished new progress about Quinoxalines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, SDS of cas: 89898-96-4.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Marques-Gallego, Patricia; Gamiz-Gonzalez, M. Amparo; Fortea-Perez, Francisco R.; Lutz, Martin; Spek, Anthony L.; Pevec, Andrej; Kozlevcar, Bojan; Reedijk, Jan published the artcile< Quinoxaline-2-carboxamide as a carrier ligand in two new platinum(II) compounds: Synthesis, crystal structure, cytotoxic activity and DNA interaction>, Product Details of C9H7N3O, the main research area is crystal structure platinum quinoxalinecarboxamide chloro solvent complex; platinum quinoxalinecarboxamide chloro solvent preparation DNA binding unwinding cytotoxicity; ethylguanine substitution platinum quinoxalinecarboxamide chloro solvent DNA model; antitumor platinum quinoxalinecarboxamide chloro solvent complex.

The search for platinum compounds structurally different from cisplatin has led to two new platinum(II) compounds containing quinoxaline-2-carboxamide as a carrier ligand, i.e. cis-[Pt(qnxca)(MeCN)Cl2] (1) and the [Pt(qnxca-H)(DMSO)Cl] (2). Both compounds have been synthesized and characterized using different spectroscopic methods. In addition, single-crystal structures have been determined by X-Ray diffraction for both compounds In each case a square planar Pt(II) is present; in (1) the qnxca is monodentate and neutral, whereas in (2) the ligand has lost a hydrogen, to form the anionic chelating ligand abbreviated as qnxca-H. The biol. activity of both compounds has been investigated in a panel of seven human tumor cells, displaying poor cytotoxic activity, compared to cisplatin. The interaction of the new compounds with 1 or 2 equivalent of 9-ethylguanine has been studied using 1H NMR, 195Pt NMR and ESI-MS spectroscopy, finding poor reactivity of 1 towards the model base, forming only the monosubstituted adduct. Surprisingly, compound 2, which is more sterically crowded, interacts more efficiently with the 9-EtG, forming a bifunctional adduct with two 9-EtG with substitution of the DMSO and the chloride ligand. Unwinding studies of pUC19 plasmid DNA by compound 1 show similar unwinding properties to cisplatin.

Dalton Transactionspublished new progress about Antitumor agents. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Product Details of C9H7N3O.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Niculescu, A. B.; Le-Niculescu, H.; Roseberry, K.; Wang, S.; Hart, J.; Kaur, A.; Robertson, H.; Jones, T.; Strasburger, A.; Williams, A.; Kurian, S. M.; Lamb, B.; Shekhar, A.; Lahiri, D. K.; Saykin, A. J. published the artcile< Blood biomarkers for memory: toward early detection of risk for Alzheimer disease, pharmacogenomics, and repurposed drugs>, Computed Properties of 163769-88-8, the main research area is Alzheimer disease blood biomarker memory pharmacogenomics.

We carried out longitudinal within-subject studies in male and female psychiatric patients to discover blood gene expression biomarkers that track short term memory as measured by the retention measure in the Hopkins Verbal Learning Test. These biomarkers were subsequently prioritized with a convergent functional genomics approach using previous evidence in the field implicating them in AD. The best overall evidence was for a series of new, as well as some previously known genes, which are now newly shown to have functional evidence in humans as blood biomarkers: RAB7A, NPC2, TGFB1, GAP43, ARSB, PER1, GUSB, and MAPT. Addnl. top blood biomarkers include GSK3B, PTGS2, APOE, BACE1, PSEN1, and TREM2, well known genes implicated in AD by previous brain and genetic studies, in humans and animal models, which serve as reassuring de facto pos. controls for our whole-genome gene expression discovery approach. A majority of top biomarkers also have evidence for involvement in other psychiatric disorders, particularly stress, providing a mol. basis for clin. co-morbidity and for stress as an early precipitant/risk factor. Some of them are modulated by existing drugs, such as antidepressants, lithium and omega-3 fatty acids. Other drug and nutraceutical leads were identified through bioinformatic drug repurposing analyses (such as pioglitazone, levonorgestrel, salsolidine, ginkgolide A, and icariin).

Molecular Psychiatrypublished new progress about Alzheimer disease. 163769-88-8 belongs to class quinoxaline, and the molecular formula is C22H21N3O2, Computed Properties of 163769-88-8.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider