Month: November 2022

Lee, Sujin published the artcileNanomolar-Potency 1,2,4-Triazoloquinoxaline Inhibitors of the Kidney Urea Transporter UT-A1, SDS of cas: 25983-14-6, the main research area is triazolo quinoxaline analog preparation renal urea transporter inhibitor diuretic.

Urea transporter A (UT-A) isoforms encoded by the Slc14a2 gene are expressed in kidney tubule epithelial cells, where they facilitate urinary concentration UT-A1 inhibition is predicted to produce a unique salt-sparing diuretic action in edema and hyponatremia. Here we report the discovery of 1,2,4-triazoloquinoxalines and the anal. of 37 synthesized analogs. The most potent compound, 8ay, containing 1,2,4-triazolo[4,3-a]quinoxaline-substituted benzenesulfonamide linked by an aryl ether, rapidly and reversibly inhibited UT-A1 urea transport by a noncompetitive mechanism with IC50 ≈ 150 nM; the IC50 was ∼2 μM for the related urea transporter UT-B encoded by the Slc14a1 gene. Mol. modeling suggested a putative binding site on the UT-A1 cytoplasmic domain. In vitro metabolism showing quinoxaline ring oxidation prompted the synthesis of metabolically stable 7,8-difluoroquinoxaline analog 8bl, which when administered to rats produced marked diuresis and reduced urinary osmolality. 8bl has substantially improved UT-A1 inhibition potency and metabolic stability compared with prior compounds

Journal of Medicinal Chemistry published new progress about Diuretics. 25983-14-6 belongs to class quinoxaline, name is 2,3,6,7-Tetrachloroquinoxaline, and the molecular formula is C8H2Cl4N2, SDS of cas: 25983-14-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Kolli, Sunder Kumar published the artcileLigand-free Pd-catalyzed C-N cross-coupling/cyclization strategy: An unprecedented access to 1-thienyl pyrroloquinoxalines for the new approach towards apoptosis, Related Products of quinoxaline, the main research area is thienyl pyrroloquinoxaline preparation PDE4 inhibitor apoptosis hepatotoxicity; Apoptosis; PDE4; Palladium; Pyrroloquinoxaline; Zebrafish.

The link between PDE4 and apoptosis prompted us to design and synthesize for the first time a series of novel 1-thienyl pyrroloquinoxalines as potential PDE4 inhibitors/apoptotic agents. A ligand-free Pd-catalyzed C-N cross-coupling/cyclization strategy has been developed for the rapid and milder access to this class of compounds some of which showed interesting pharmacol. properties when tested in vitro and in zebrafish embryos.

European Journal of Medicinal Chemistry published new progress about Apoptosis. 39267-05-5 belongs to class quinoxaline, name is 2,3-Dichloro-6-methylquinoxaline, and the molecular formula is C9H6Cl2N2, Related Products of quinoxaline.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Romer, Duane R. published the artcileSynthesis and fungicidal activity of 1,4-dithiino[2,3-b]quinoxaline-2,3-dicarbonitriles, Recommanded Product: 2,3-Dichloro-6-methylquinoxaline, the main research area is quinoxaline derivative fungicide structure activity.

A series of 11 1,4-dithiino[2,3-b]quinoxaline-2,3-dicarbonitriles (I, R1 = H, Cl, CF3, MeO, CN, Ac, NO2; R2 = H, Cl Me, NO2) was prepared by reaction of 2,3-dichloroquinoxalines with disodium (Z)-2,3-dimercapto-2-butenedinitrile in N,N-dimethylformamide. These products were tested for in-vitro fungicidal activity by a Min. Inhibitory Concentration method. Several of these compounds showed broad-spectrum fungicidal activity. The activity exhibited by these compounds was greatly dependent upon the substituents of the quinoxaline ring, with the nitro-substituted derivatives showing the highest levels of antifungal activity. None of the compounds prepared, however, showed fungicidal activity comparable to that of the com. fungicides screened.

Pesticide Science published new progress about Fungicides. 39267-05-5 belongs to class quinoxaline, name is 2,3-Dichloro-6-methylquinoxaline, and the molecular formula is C9H6Cl2N2, Recommanded Product: 2,3-Dichloro-6-methylquinoxaline.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Tomoda, Haruhiko published the artcileSynthesis and physical properties of pyrido[1′,2′:1,2]imidazo[4,5-b]quinoxalines, Product Details of C8H2Cl4N2, the main research area is pyridoimidazoquinoxaline preparation; fluorescence substituent effect pyridoimidazoquinoxaline preparation.

A series of 2-, 3-, or 4-substituted pyrido[1′,2′:1,2]imidazo[4,5-b]quinoxalines (PIQs) were synthesized in moderate-to-good yields by the reactions of 2-amino-3-chloroquinoxalines (ACQs) with substituted pyridines, and the structures were established. The reactions of ACQs with 3-phenoxycarbonyl and 3-benzoylpyridines gave the corresponding 2-substituted PIQs, while those with 3-Me, 3-Et, 3-benzyl, 3-Ph, 3-ethoxycarbonyl, and 3-acetylpyridines gave the corresponding 4-substituted PIQs. PIQ derivatives having substituents at the 2,4,8- and/or 9-positions were also studied. The spectroscopic and electrochem. properties of a series of PIQs derivatives were studied. PIQ showed a strong green fluorescence at 481.5 and 505 nm (F = 0.40) in ethanol. The introduction of substituents at the 3 position of PIQ altered the color of the fluorescence from blue to green without deteriorating the high quantum yield of PIQ. All of the derivatives showed strong (blue to orange) fluorescence in both solution and the solid state.

Bulletin of the Chemical Society of Japan published new progress about Fluorescence. 25983-14-6 belongs to class quinoxaline, name is 2,3,6,7-Tetrachloroquinoxaline, and the molecular formula is C8H2Cl4N2, Product Details of C8H2Cl4N2.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Romer, Duane R. published the artcileSynthesis of 2,3-dichloroquinoxalines via Vilsmeier reagent chlorination, Product Details of C9H6Cl2N2, the main research area is quinoxaline dichloro preparation Vilsmeier reagent chlorination dihydroxyquinoxaline.

A convenient and high-yielding synthesis of 2,3-dichloroquinoxalines from the corresponding 2,3-dihydroxyquinoxalines has been developed. Treatment of a slurry of the 2,3-dihydroxyquinoxaline with N,N-dimethylformamide in the presence of excess thionylchloride in 1,2-dichloroethane results in the rapid and high-yielding formation of the 2,3-dichloroquinoxaline derivatives Simplified workup and purification procedures for these compounds are also described.

Journal of Heterocyclic Chemistry published new progress about Chlorination. 39267-05-5 belongs to class quinoxaline, name is 2,3-Dichloro-6-methylquinoxaline, and the molecular formula is C9H6Cl2N2, Product Details of C9H6Cl2N2.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Ahmad, Yusuf published the artcileQuinoxaline derivatives. XI. Reaction of quinoxaline 1,4-dioxide and some of its derivatives with acetyl chloride, Formula: C9H6Cl2N2, the main research area is quinoxaline dioxide reaction; acetyl chloride reaction; chloroquinoxaline dioxide.

Quinoxaline 1,4-dioxide with AcCl gives 6-chloroquinoxaline 1-oxide (I). On heating, and progressively increasing the time of reaction, the yield of I increases, and 3-chloroquinoxaline 1-oxide, and 6.7-dichloroquinoxaline appear as addnl. products. 7-Ethoxy-, 7-methoxy-, 7-methylquinoxaline 1,4-dioxides show a similar behavior, giving corresponding 6-chloro, and 3-chloro derivatives as main products. Further increase in the reaction time results in the formation of 2,6-dichloro and 2,3-dichloro compounds as addnl. products. However, none of the 2-chloro 4-oxide derivatives were isolated. The mechanisms for these transformations were proposed and discussed.

Journal of Organic Chemistry published new progress about Chlorination. 39267-05-5 belongs to class quinoxaline, name is 2,3-Dichloro-6-methylquinoxaline, and the molecular formula is C9H6Cl2N2, Formula: C9H6Cl2N2.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Babu, P. Vijaya published the artcileLigand/PTC-free intramolecular Heck reaction: synthesis of pyrroloquinoxalines and their evaluation against PDE4/luciferase/oral cancer cell growth in vitro and zebrafish in vivo, Synthetic Route of 39267-05-5, the main research area is PDE4 luciferase mouth cancer cell proliferation zebrafish; pyrroloquinoxaline preparation PDE4 inhibitor; dichloroquinoxaline intramol Heck reaction.

A series of 1,3-disubstituted pyrrolo[2,3-b]quinoxalines was designed for the potential inhibition of PDE4 without inhibiting luciferase. A ligand/PTC (phase transfer catalyst) free intramol. Heck cyclization strategy was used to prepare these compounds, some of which showed significant inhibition of PDE4B (IC50 ≈ 5-14 μM) and growth inhibition of oral cancer cells (CAL 27) but not inhibition of luciferase in vitro. They also showed acceptable safety profiles but no apoptosis in zebrafish embryos.

Organic & Biomolecular Chemistry published new progress about Heck reaction. 39267-05-5 belongs to class quinoxaline, name is 2,3-Dichloro-6-methylquinoxaline, and the molecular formula is C9H6Cl2N2, Synthetic Route of 39267-05-5.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Lian, Mi published the artcileLogic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1,2-diamines, SDS of cas: 40353-41-1, the main research area is quinoxaline preparation; iodination oxidation cyclization aryl ketone diamine; phenylene diamine iodination oxidation cyclization aryl ketone.

A novel protocol for the synthesis of quinoxalines has been developed from simple ketones and 1,2-diamines. This process underwent a logic approach to bis-substituted quinoxalines via a consecutive iodination/Kornblum oxidation/cyclization in the presence of I2/CuO/DMSO and to mono-substituted quinoxalines via an iodination/cyclization/aromatization in the presence of I2/CuO/K3PO4·3H2O.

Tetrahedron published new progress about Aromatization. 40353-41-1 belongs to class quinoxaline, name is 2-(Thiophen-2-yl)quinoxaline, and the molecular formula is C12H8N2S, SDS of cas: 40353-41-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Sarges, Reinhard published the artcile4-Amino[1,2,4]triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants, SDS of cas: 25983-14-6, the main research area is triazoloquinoxaline preparation biol activity; aminotriazolquinoxaline adenosine receptor antagonist; antidepressant aminotriazoloquinoxaline.

A series of 4-amino[1,2,4]triazolo[4,3-a]quinoxalines (I; R = H, alkyl, OMe, etc.; R1 = amino; R2 = H, F, Cl, OMe) have been prepared from 2,3-dichloroquinoxaline II (same R2). E.g., treating II with NH2NH2, followed by cyclization with ortho esters RC(OR3)3 (same R; R3 = alkyl), and subsequent amination, gave I. Many compounds from this class reduce immobility in Porsolt’s behavioral despair model in rats upon acute administration and may therefore have therapeutic potential as novel and rapid acting antidepressant agents. Optimal activity in this test is associated with hydrogen, CF3, or small alkyl groups in the 1-position, with NH2, NH-acetyl, or amines substituted with small alkyl groups in the 4-position, and with hydrogen or 8-halo substituents in the aromatic ring. Furthermore, many I bind avidly, and in some cases very selectively, to adenosine A1 and A2 receptors. A1 affinity of these compounds was measured by their inhibition of tritiated CHA (N6-cyclohexyladenosine) binding in rat cerebral cortex membranes and A2 affinity by their inhibition of tritiated NECA [5′-(N-ethylcarbamoyladenosine] binding to rat striatal homogenate in the presence of cold N6-cyclopentyladenosine. Structure-activity relationship studies show that best A1 affinity is associated with Et, CF3, or C2F5 in the 1-position, NHCHMe2 or NH-cycloalkyl in the 4-position, and with an 8-chloro substituent. Affinity at the A2 receptor is mostly dependent on the presence of an NH2 group in the 4-position and is enhanced by Ph, CF3, or Et in the 1-position. The most selective A1 ligand by a factor of >3000 is 8-chloro-4-(cyclohexylamino)-1-(trifluoromethyl)[1,2,4]triazolo[4,3-a]quinoxaline). The most potent A2 ligand is 4-amino-8-chloro-1-phenyl[1,2,4]triazolo[4,3-a]quinoxaline. Representatives from this series appear to act as antagonists at both A1 and A2 receptors since they antagonize the inhibiting action of CHA on norepinephrine-stimulated cAMP formation in fat cells and they decrease cAMP accumulation induced by adenosine in limbic forebrain slices. Thus certain members of I are among the most potent and A1 or A2 selective non-xanthine adenosine antagonists known.

Journal of Medicinal Chemistry published new progress about Antidepressants. 25983-14-6 belongs to class quinoxaline, name is 2,3,6,7-Tetrachloroquinoxaline, and the molecular formula is C8H2Cl4N2, SDS of cas: 25983-14-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Zhu, Zhijian published the artcileSynthesis of imidazo[4,5-b]quinoxaline ribonucleosides as linear dimensional analogs of antiviral polyhalogenated benzimidazole ribonucleosides, Product Details of C8H2Cl4N2, the main research area is benzimidazole nucleoside linear dimensional analog preparation; imidazoquinoxaline ribonucleoside preparation virucide cytotoxicity.

We have recently found that 2,5,6-trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB) and the corresponding 2-bromo analog have better in vitro activities against HCMV than the clin. used agents ganciclovir and foscarnet. These benzimidazole nucleosides act by a unique mechanism, however, their biol. target has not been completely identified. As an approach to probing the target, we have designed imidazo[4,5-b]quinoxaline nucleosides as linear dimensional analogs of the benzimidazole nucleosides to study the spatial limitation of the binding site in the target enzyme. A convenient route was developed for the synthesis of 2-substituted 6,7-dichloroimidazo[4,5-b]quinoxalines involving a reaction of 2,3,6,7- tetrachloroquinoxaline with ammonia followed by a ring annulation as the key step. This furnished the versatile heterocycle 6,7-dichloroimidazo[4,5-b]quinoxalin-2-one. Ribosylation of 2-substituted imidazo[4,5- b]quinoxalines was influenced by the functional group at the 2-position and the 2-one compound was found to smoothly undergo ribosylation. The 2-one group of the nucleoside was converted into specifically selected 2-substituted compounds Evaluation of the compounds for activity against two herpes viruses and for cytotoxicity showed they were less active and/or more cytotoxic than TCRB. We conclude therefore, that the binding pocket on the protein target of TCRB will tolerate some electronic and size changes.

Journal of the Chinese Chemical Society (Taipei) published new progress about Antiviral agents. 25983-14-6 belongs to class quinoxaline, name is 2,3,6,7-Tetrachloroquinoxaline, and the molecular formula is C8H2Cl4N2, Product Details of C8H2Cl4N2.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider