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High-affinity partial agonist imidazo[1,5-a]quinoxaline amides, carbamates, and ureas at the gamma-aminobutyric acid A/benzodiazepine receptor complex

A series of imidazo[1,5-a]quinoxaline amides, carbamates, and ureas which have high affinity for the gamma-aminobutyric acid A/benzodiazepine receptor complex was developed. Compounds within this class have varying efficacies ranging from antagonists to full agonists. However, most analogs were found to be partial agonists as indicated by [35S]TBPS and Cl- current ratios. Many of these compounds were also effective in antagonizing metrazole-induced seizures in accordance with anticonvulsant and possible anxiolytic activity. Selected quinoxalines displayed limited benzodiazepine-type side effects such as ethanol potentiation and physical dependence in animal models. Dimethylamino urea 41 emerged as the most interesting analog, having a partial agonist profile in vitro while possessing useful activity in animal models of anxiety such as the Vogel and Geller assays. In accordance with its partial agonist profile, 41 was devoid of typical benzodiazepine side effects.

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Let¡¯s face it, organic chemistry can seem difficult to learn. 59564-59-9. Especially from a beginner¡¯s point of view. Like 59564-59-9, Name is 3,4-Dihydroquinoxalin-2(1H)-one. In a document type is Article, introducing its new discovery.

Piperazine imidazo[1,5-a]quinoxaline ureas as high-affinity GABA(A) ligands of dual functionality

A series of imidazo[1,5-a]quinoxaline piperazine ureas appended with a tert-butyl ester side chain at the 3-position was developed. Analogues within this series have high affinity for the gamma-aminobutyric acid A (GABA(A))/benzodiazepine receptor complex with efficacies ranging from inverse agonists to full agonists. Many analogues were found to be partial agonists as indicated by [35S]TBPS and Cl- current ratios. Uniquely, a number of these analogues were found to have a bell-shaped dose-response profile in the alpha1beta2gamma2 subtype as determined by whole cell patch-clamp technique, where in vitro efficacy was found to decrease with increasing drug concentration. Many of the compounds from this series were effective in antagonizing metrazole-induced seizures, consistent with anticonvulsant and possibly anxiolytic activity. Additionally, several analogues were also effective in lowering cGMP levels (to control values) after applied stress, also consistent with anxiolytic-like properties. The most effective compounds in these screens were also active in animal models of anxiety such as the Vogel and Geller assays. The use of the piperazine substituent allowed for excellent drug levels and a long duration of action in the central nervous system for many of the quinoxalines, as determined by ex vivo assay. Pharmacokinetic analysis of several compounds indicated excellent oral bioavailability and a reasonable half-life in rats. From this series emerged two partial agonists (55, 91) which had good activity in anxiolytic models, acceptable pharmacokinetics, and minimal benzodiazepine-type side effects.

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59564-59-9, Name is 3,4-Dihydroquinoxalin-2(1H)-one, belongs to quinoxaline compound, is a common compound. 59564-59-9In an article, authors is Akula, Pavan Sudheer, once mentioned the new application about 59564-59-9.

Visible-light-induced C(sp3)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1: H)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions

A convenient photocatalyzed oxidative coupling reaction of 4-alkyl-3,4-dihydroquinoxalin-2(1H)-one and its derivatives with a variety of nucleophiles was developed with a ruthenium photoredox catalyst and oxygen under a household compact fluorescent light. With a slower reaction rate, the cross coupling transformation can be achieved in the absence of an external photocatalyst with a similar isolated yield. An application to the synthesis of natural product cephalandole A was also demonstrated.

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Quinoxaline – Wikipedia,
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Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.59564-59-9. In my other articles, you can also check out more blogs about 59564-59-9

59564-59-9, A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 59564-59-9, Name is 3,4-Dihydroquinoxalin-2(1H)-one, molecular formula is C8H8N2O. In a Article, authors is Pan, Yixiao£¬once mentioned of 59564-59-9

Ru-Catalyzed Deoxygenative Transfer Hydrogenation of Amides to Amines with Formic Acid/Triethylamine

A ruthenium(II)-catalyzed deoxygenative transfer hydrogenation of amides to amines using HCO2H/NEt3 as the reducing agent is reported for the first time. The catalyst system consisting of [Ru(2-methylallyl)2(COD)], 1,1,1-tris(diphenylphosphinomethyl) ethane (triphos) and Bis(trifluoromethane sulfonimide) (HNTf2) performed well for deoxygenative reduction of various secondary and tertiary amides into the corresponding amines in high yields with excellent selectivities, and exhibits high tolerance toward functional groups including those that are reduction-sensitive. The choice of hydrogen source and acid co-catalyst is critical for catalysis. Mechanistic studies suggest that the reductive amination of the in situ generated alcohol and amine via borrowing hydrogen is the dominant pathway. (Figure presented.).

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.59564-59-9,3,4-Dihydroquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.

59564-59-9, EXAMPLE 294 4-Methoxycarbonyl-1,2,3,4-tetrahydroquinoxalin-2-one (IV) To 2.99 g of 1,2,3,4-tetrahydroquinoxalin-2-one (IV) in 30 ml of methyl tert-butyl ether are added 2.18 ml of methyl chloroformate. After stirring for 1 hr, 4.9 ml of diisopropylethylamine are added. The reaction is stirred an additional 30 min and then concentrated under reduced pressure. The residue is partitioned between dichloromethane and aq. sodium bicarbonate and the organic layers dried over sodium sulfate and concentrated. The crude product is crystallized from dichloromethane/hexane/ethyl ether to give the title compound, NMR (CDCl3) 3.84, 4.45, 6.87, 7.11, 7.65, 8.27 delta.

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Reference£º
Patent; The Upjohn Company; US5541324; (1996); A;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

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The synthetic route of 59564-59-9 has been constantly updated, and we look forward to future research findings.

59564-59-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.59564-59-9,3,4-Dihydroquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.

A solution of 3,4-dihydroquinoxalin-2-(1H)-one (2.9 g, 19.6 mmol) in methanol (20 mL) Sodium cyanoborohydride (2.5 g, 39.7 mmol) was added, Paraformaldehyde (0.9 g) and glacial acetic acid (1 mL) The reaction was stirred at 25 C for 4 hours, Sodium cyanoborohydride (1.2 g, 19.0 mmol) was added, Paraformaldehyde (0.45 g) and hydrochloric acid (0.5 mL), The reaction was heated to 50 C for 5 hours. The reaction solution was cooled to room temperature, The pH was adjusted to 8 with saturated aqueous sodium bicarbonate solution, Ethyl acetate (50 mL x 3) was added, Combine organic phase, Dried over anhydrous sodium sulfate, filter, concentrate, To give the title compound (3.0 g, yield 94.5%).

The synthetic route of 59564-59-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shandong Xuanzhu Pharmaceutical Co., Ltd.; Wu, Yongqian; (31 pag.)CN106317027; (2017); A;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

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59564-59-9 3,4-Dihydroquinoxalin-2(1H)-one 185949, aquinoxaline compound, is more and more widely used in various fields.

59564-59-9, 3,4-Dihydroquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 80 5-Methyl-4-(1,2,3,4-tetrahydro-3-oxo-1-quinoxalinyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic Acid Methyl Ester Example 27 (23 mg, 0.1 mmol) was stirred with 1,2,3,4-tetrahydroquinoxalin-2-one (44.4 mg, 0.3 mmol) in DMF (0.5 mL) for 1 hr at 50 C. Water was added and the resulting solid material was collected, washed with water and dried. The material was triturated with methanol, filtered, and dried again to provide 20 mg (59%) of a white solid. 1H NMR (d-DMSO): delta 8.30-8.25 (m, 2H), 7.12-7.03 (m, 2H), 6.83 (br s, 2H), 4.38 (s, 2H), 3.73 (s, 3H), 2.49 (s, 3H), 1.72 (s, 3H)., 59564-59-9

59564-59-9 3,4-Dihydroquinoxalin-2(1H)-one 185949, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol Myers Squibb Company; US6982265; (2006); B1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

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As the paragraph descriping shows that 59564-59-9 is playing an increasingly important role.

59564-59-9, 3,4-Dihydroquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

59564-59-9, 24b. 4-methyl-3,4-dihydroquinoxalin-2(1H)-one To a solution of 24a (500 mg, 3.378 mmol) in MeOH (3 mL) was added NaBH3CN (425 mg, 6.76 mmol), paraformaldehyde (102 mg), followed by HOAc (30 muL). The reaction mixture was stirred at rt for 4 h. Another portion of NaBH4CN (212 mg, 3.37 mmol) and parafornaldehyde (51 mg) were added to the reaction mixture along with conc. HCl (10 muL). The reaction mixture was stirred at 50 C. for 5 h and cooled to rt. The pH was adjusted to 8 and the solvent was evaporated under reduced pressure. The desired product was extracted into EtOAc and washed it with brine, dried over Na2SO4. The solvent was evaporated under reduced pressure to afford 24b (537 mg, 98%) as beige powder. LC-MS ESI m/z 163 [M+H]+.

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Reference£º
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

Brief introduction of 59564-59-9

The synthetic route of 59564-59-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.59564-59-9,3,4-Dihydroquinoxalin-2(1H)-one,as a common compound, the synthetic route is as follows.

59564-59-9, 24b. 4-methyl-3,4-dihydroquinoxalin-2(1H)-one To a solution of 24a (500 mg, 3.378 mmol) in MeOH (3 mL) was added NaBH3CN (425 mg, 6.76 mmol), paraformaldehyde (102 mg), followed by HOAc (30 muL). The reaction mixture was stirred at rt for 4 h. Another portion of NaBH4CN (212 mg, 3.37 mmol) and parafornaldehyde (51 mg) were added to the reaction mixture along with conc. HCl (10 muL). The reaction mixture was stirred at 50 C. for 5 h and cooled to rt. The pH was adjusted to 8 and the solvent was evaporated under reduced pressure. The desired product was extracted into EtOAc and washed it with brine, dried over Na2SO4. The solvent was evaporated under reduced pressure to afford 24b (537 mg, 98%) as beige powder. LC-MS ESI m/z 163 [M+H]+.

The synthetic route of 59564-59-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider

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59564-59-9 3,4-Dihydroquinoxalin-2(1H)-one 185949, aquinoxaline compound, is more and more widely used in various fields.

59564-59-9, 3,4-Dihydroquinoxalin-2(1H)-one is a quinoxaline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 3,4-dihydroquinoxalin-2-(1H)-one (2.9 g, 19.6 mmol) in methanol (20 mL) Sodium cyanoborohydride (2.5 g, 39.7 mmol) was added, Paraformaldehyde (0.9 g) and glacial acetic acid (1 mL) The reaction was stirred at 25 C for 4 hours, Sodium cyanoborohydride (1.2 g, 19.0 mmol) was added, Paraformaldehyde (0.45 g) and hydrochloric acid (0.5 mL), The reaction was heated to 50 C for 5 hours. The reaction solution was cooled to room temperature, The pH was adjusted to 8 with saturated aqueous sodium bicarbonate solution, Ethyl acetate (50 mL x 3) was added, Combine organic phase, Dried over anhydrous sodium sulfate, filter, concentrate, To give the title compound (3.0 g, yield 94.5%)., 59564-59-9

59564-59-9 3,4-Dihydroquinoxalin-2(1H)-one 185949, aquinoxaline compound, is more and more widely used in various fields.

Reference£º
Patent; Shandong Xuanzhu Pharmaceutical Co., Ltd.; Wu, Yongqian; (31 pag.)CN106317027; (2017); A;,
Quinoxaline – Wikipedia
Quinoxaline | C8H6N2 | ChemSpider