31910-18-6

Usage

Uses

Used in Pharmaceutical Research:
2,3-DIHYDROXY-6-METHOXYQUINOXALINE is used as a reagent for the discovery of MK-5172 (M424985), a macrocyclic analog that serves as an antiviral protease inhibitor. 2,3-DIHYDROXY-6-METHOXYQUINOXALINE plays a crucial role in the development of new antiviral drugs, particularly those targeting protease enzymes, which are essential for the replication and survival of certain viruses.

InChI:InChI=1/C9H8N2O3/c1-14-5-2-3-6-7(4-5)11-9(13)8(12)10-6/h2-4H,1H3,(H,10,12)(H,11,13)

Upstream product

• 95-92-1 oxalic acid diethyl ester 
• 102-51-2 4-methoxy-1,2-phenylenediamine 
• 39266-92-7 6-methoxyquinoxaline 1,4-dioxide 
• 96-96-8 4-methoxy-2-nitroaniline 
• 924-44-7 glyoxylic acid ethyl ester 
• 4685-47-6 3,4-dimethylanisole 
• 104-94-9 4-methoxy-aniline 
• 51-66-1 4-methoxyacetanilide 
• 119-81-3 4-methoxy-2-nitroacetanilide 
• 120951-69-1 N-(2-Formylamino-4-methoxy-phenyl)-formamide 
• 144-62-7 oxalic acid 
• 59548-39-9 4-methoxyphenylene-1,2-diamine dihydrochloride 
• 16133-49-6 5-methoxy-2-nitroaniline 
• 6153-56-6 oxalic acid dihydrate 

Downstream Products

• 39267-04-4 2,3-dichloro-6-methoxyquinoxaline 
• 60729-19-3 1,4-dimethyl-2,3-dioxo-6-methoxy-1,2,3,4-tetrahydroquinoxaline 
• 263715-90-8 3-chloro-7-methoxy-1-methylquinoxalin-2(1H)-one 
• 1206524-78-8 3-chloro-6-methoxyquinoxalin-2-ol 
• 1206524-79-9 1-(tert-butyl) 2-methyl (2S,4R)-4-((3-chloro-7-methoxyquinoxalin-2-yl)oxy)pyrrolidine-1,2-dicarboxylate 
• 1425038-23-8 methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-14-methoxy-3,6-dioxo-18,19-didehydro-1,1a,3,4,5,6,9,10,20,21,22,22a-dodecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3, 6]dioxadiazacyclononadecino[11,12-b]quinoxaline-8-carboxylate 

Relevant academic research and scientific papers

Novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and preparation and application thereof

The invention provides a novel molecular targeting anti-tumor aza-steroid derivative based on lipid toxicity and a preparation method and application thereof, and belongs to the field of chemical medicines. The derivative is a compound as shown in a formula I, or a salt thereof, or a stereoisomer thereof. The compound is low in toxicity or basically non-toxic to normal cells, has an obvious inhibition effect to tumor cell lines, particularly has good lipid toxicity selectivity to tumor cells such as liver cancer, lung cancer and the like in vivo, and has an obvious inhibition effect; meanwhile, the compound can effectively activate SREBP1 and PPAR gamma, inhibit lipid transport MTTP, cause lipid aggregation in tumor cells and cause lipid toxicity of the tumor cells. The compound can be used for treating liver cancer, lung cancer and the like in a molecular targeting manner, is low in toxicity or even non-toxic, and has a good application prospect.

Synthesis and vasorelaxant evaluation of novel 7-methoxyl-2,3-disubstituted-quinoxaline derivatives

An array of novel 7-methoxyl-2,3-disubstituted quinoxaline derivatives was designed, synthesized and their potential antihypertensive activities were examined, in an attempt to discover potent small molecules with vasorelaxant effects. The vasoactivities of these compounds on vascular tone, as well as underlying mechanisms were hereby explored. Results showed that five compounds (7s, 7t, 7v, 7w, 7γ) could induce endothelium-independent relaxation in high extracellular K+- and phenylephrine-precontracted C57 mice aortic rings. These five compounds, unlike other commonly used vasodilators, could slowly but effectively inhibit vasoconstriction.

NS3/4A protease inhibitor intermediate as well as synthesis method and application thereof

The invention belongs to the technical field of medicine, and particularly relates to an NS3/4A protease inhibitor intermediate as well as a synthesis method and application thereof. The synthesis method comprises the following steps: taking 4-methoxy-o-p

HEPATITIS C VIRUS NS3/4A PROTEASE INHIBITORS

The invention provides novel classes of HCV therapeutics that are orally available, safe and effective HCV NS3/4A protease inhibitors and are less susceptible to drug resistance than existing therapeutics. The invention also relates to pharmaceutical composition of these compounds and methods of preparation and use thereof.

A One-pot Facile Synthesis of 2,3-Dihydroxyquinoxaline and 2,3-Dichloroquinoxaline Derivatives Using Silica Gel as an Efficient Catalyst

An efficient one-pot reaction has been developed for the synthesis of 2,3-dichloroquinoxaline derivatives 3a–n. The reaction was performed in two steps via a silica gel catalyzed tandem process from o-phenylenediamine and oxalic acid, followed by addition of phosphorus oxychloride (POCl3). A variety of 2,3-dichloroquinoxalines have been obtained in good to excellent overall yields. Eight known compounds 3a–3h were characterized by IR, 1H-NMR, and mass spectroscopies. Compounds 3i–3n without spectroscopic data were characterized by IR, 1H-NMR, 13C-NMR, and mass spectroscopies.

Hepatitis C Virus NS3/4A Protease Inhibitors Incorporating Flexible P2 Quinoxalines Target Drug Resistant Viral Variants

A substrate envelope-guided design strategy is reported for improving the resistance profile of HCV NS3/4A protease inhibitors. Analogues of 5172-mcP1P3 were designed by incorporating diverse quinoxalines at the P2 position that predominantly interact with the invariant catalytic triad of the protease. Exploration of structure-activity relationships showed that inhibitors with small hydrophobic substituents at the 3-position of P2 quinoxaline maintain better potency against drug resistant variants, likely due to reduced interactions with residues in the S2 subsite. In contrast, inhibitors with larger groups at this position were highly susceptible to mutations at Arg155, Ala156, and Asp168. Excitingly, several inhibitors exhibited exceptional potency profiles with EC50 values ≤5 nM against major drug resistant HCV variants. These findings support that inhibitors designed to interact with evolutionarily constrained regions of the protease, while avoiding interactions with residues not essential for substrate recognition, are less likely to be susceptible to drug resistance.

NOVEL FYN KINASE INHIBITORS

The present invention relates to the novel therapies to treat neurodegenerative diseases such as Parkinson's disease (PD). The present invention relates to novel small molecule inhibitors of Fyn Kinase and for testing activity against Parkinsons's disease models compounds that inhibit Fyn kinase having the following formula. (I)

Process and intermediates for preparing macrolactams

The present invention includes compounds useful as intermediates in the preparation of macrolactams, methods for preparing the intermediates, and methods for preparing macrolactams from the intermediates. One use of the methods and intermediates described herein is in the production of macrolactam compounds able to inhibit HCV NS3 protease activity. HCV NS3 inhibitory compounds have therapeutic and research applications.

A N-acetyl-acetyl-6-methoxy-7-amino-quinoxalin -2,3-dione method for the preparation of

The invention discloses a preparation method of N-acetoaetyl-6-methoxy-7-aminoqunoxaline-2,3-diketone, which comprises the following steps: adding an ethanol aqueous solution, iron powder and hydrochloric acid, heating to 70-90 DEG C, adding bordeaux base GP under the protection of nitrogen, performing thermal insulation for 4-6h, adjusting the pH value, then adding diethyl oxalate and a catalyst, performing thermal insulation for 8-12h, cooling to 10-45 DEG C, and filtering to obtain off-white solid 1,4-dihydro-6-methoxy-2,3-quinoxalinedione; heating a salpeter solution to 70-90 DEG C, adding 1,4-dihydro-6-methoxy-2,3-quinoxalinedione, performing thermal insulation, then cooling, performing suction filtration and washing to obtain 1,4-dihydro-6-methoxy-7-nitro-2,3-quinoxalinedione, performing catalytic hydrogenation on 1,4-dihydro-6-methoxy-7-nitro-2,3-quinoxalinedione, and adding a catalyst and water for reaction at the pressure of 0.2-2 MPa and temperature of 80-120 DEG C, cooling to 80-90 DEG C after reaction, performing suction filtration, adjusting the pH value, dropwise adding diketene, performing thermal insulation, cooling to 15-40 DEG C, and performing suction filtration to obtain N-acetoaetyl-6-methoxy-7-aminoqunoxaline-2,3-diketone. The total yield of the finished product is more than 82%, and the purity is more than 99.0%.

MACROCYCLIC AND BICYCLIC INHIBITORS OF HEPATITIS C VIRUS

Compounds of formula (I):or pharmaceutically acceptable salts thereof, wherein the various substituents are defined herein, methods of using said compounds, and pharmaceutical compositions containing said compounds.