Tag: M.W=150-200

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>, Application of C9H7N3O, 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, Application of C9H7N3O.

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)>, Application In Synthesis of 89898-96-4, 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, Application In Synthesis of 89898-96-4.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Hirota, Takashi; Namba, Tetsuto; Sasaki, Kenji published the artcile< Polycyclic N-hetero compounds. XXII. Reaction of pyridine N-oxides and pyrazine di-N-oxides with formamide>, Recommanded Product: Quinoxaline-2-carboxamide, the main research area is carbamoylation pyrazine dioxide formamide; pyrazinecarboxamide; quinoline oxide carbamoylation formamide; quinoxaline dioxide carbamoylation formamide; lutidine oxide carbamoylation formamide.

Quinoxaline 1,4-dioxides and pyrazine 1,4-dioxide were heated with HCONH2 to give quinoxalinecarboxamides and pyrazinecarboxamide. Similarly, 2,6-dimethylpyridine 1-oxide gave 2,6-dimethylisonicotinamide. 2,4-Dimethylquinoline 1-oxide gave 2,4-dimethyl-5-quinoxalinecarboxamide and 4-methyl-2-(5-pyrimidinyl)quinoline.

Journal of Heterocyclic Chemistry published new progress about Carbamoylation. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Recommanded Product: Quinoxaline-2-carboxamide.

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>, Category: quinoxaline, 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, Category: quinoxaline.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Wakelin, Laurence P. G.; Waring, Michael J. published the artcile< The binding of echinomycin to deoxyribonucleic acid>, Computed Properties of 5182-90-1, 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, Computed Properties 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>, 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

Le Douaron, Gael; Ferrie, Laurent; Sepulveda-Diaz, Julia E.; Amar, Majid; Harfouche, Abha; Seon-Meniel, Blandine; Raisman-Vozari, Rita; Michel, Patrick P.; Figadere, Bruno published the artcile< New 6-Aminoquinoxaline Derivatives with Neuroprotective Effect on Dopaminergic Neurons in Cellular and Animal Parkinson Disease Models>, Safety of 7-Nitro-2(1H)-quinoxalinone, the main research area is aminoquinoxaline preparation arylation alkynylation reaction neuroprotective effect dopamine neuron; Parkinson disease model neuroprotective effect dopamine aminoquinoxaline derivative.

Parkinson’s disease (PD) is a neurodegenerative disorder of aging characterized by motor symptoms that result from the loss of midbrain dopamine neurons and the disruption of dopamine-mediated neurotransmission. There is currently no curative treatment for this disorder. To discover druggable neuroprotective compounds for dopamine neurons, the authors have designed and synthesized a 2nd-generation of quinoxaline-derived mols. based on structure-activity relation studies, which led previously to the discovery of the authors’ 1st neuroprotective brain penetrant hit compound MPAQ (5c). Neuroprotection assessment in PD cellular models of the authors’ newly synthesized quinoxaline-derived compounds led to the selection of a better hit compound, PAQ (4c). Extensive in vitro characterization of 4c showed that its neuroprotective action is partially attributable to the activation of reticulum endoplasmic ryanodine receptor channels. Most interestingly, 4c was able to attenuate neurodegeneration in a mouse model of PD, making this compound an interesting drug candidate for the treatment of this disorder.

Journal of Medicinal Chemistry published new progress about Alkynylation. 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, Safety of 7-Nitro-2(1H)-quinoxalinone.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Hirota, Takashi; Namba, Tetsuto; Sasaki, Kenji published the artcile< Polycyclic N-hetero compounds. XXII. Reaction of pyridine N-oxides and pyrazine di-N-oxides with formamide>, SDS of cas: 5182-90-1, the main research area is carbamoylation pyrazine dioxide formamide; pyrazinecarboxamide; quinoline oxide carbamoylation formamide; quinoxaline dioxide carbamoylation formamide; lutidine oxide carbamoylation formamide.

Quinoxaline 1,4-dioxides and pyrazine 1,4-dioxide were heated with HCONH2 to give quinoxalinecarboxamides and pyrazinecarboxamide. Similarly, 2,6-dimethylpyridine 1-oxide gave 2,6-dimethylisonicotinamide. 2,4-Dimethylquinoline 1-oxide gave 2,4-dimethyl-5-quinoxalinecarboxamide and 4-methyl-2-(5-pyrimidinyl)quinoline.

Journal of Heterocyclic Chemistry published new progress about Carbamoylation. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, SDS of cas: 5182-90-1.

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

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