35676-70-1

Usage

Uses

Used in Pharmaceutical Research:
2-Chloro-3-hydroxyquinoxaline is used as a key intermediate in the development of new drugs due to its potential biological activity and structural versatility. Its unique chemical properties allow for the synthesis of a wide range of organic compounds with potential therapeutic applications.
Used in Organic Synthesis:
As a versatile building block, 2-Chloro-3-hydroxyquinoxaline is employed in the synthesis of various organic compounds. Its reactivity and functional groups enable the formation of diverse chemical structures, making it a valuable component in organic chemistry.
Used in Pesticide Production:
2-Chloro-3-hydroxyquinoxaline serves as an intermediate in the production of certain pesticides. Its chemical properties contribute to the development of effective pest control agents, enhancing agricultural productivity and crop protection.
Used in Antitumor and Antimicrobial Research:
2-Chloro-3-hydroxyquinoxaline has been studied for its potential antitumor and antimicrobial activities. Its biological activity makes it a promising candidate for further research and development in the fields of oncology and infectious diseases, offering new therapeutic options for various health challenges.

InChI:InChI=1/C8H5ClN2O/c9-7-8(12)11-6-4-2-1-3-5(6)10-7/h1-4H,(H,11,12)

Upstream product

• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 2213-63-0 2,3-dichloroquinoxaline 
• 95-54-5 1,2-diamino-benzene 
• 49568-68-5 3-chloroquinoxaline-2-carboxaldehyde 
• 15804-19-0 quinoxaline-2,3-dione 
• 1050514-29-8 2-[(dimethylamino)methyl]-1-methyl-1H-imidazole-4-sulfonamide 

Downstream Products

• 1445-69-8 4-hydroxy-1(2H)-phthalazinone 
• 15804-19-0 quinoxaline-2,3-dione 
• 2213-63-0 2,3-dichloroquinoxaline 
• 35015-91-9 3-amino-2(1H)-quinoxalinone 
• 1374748-69-2 2-(3-((4-fluorophenyl)amino)-2-oxoquinoxalin-1(2H)-yl)acetic acid 
• 1374748-70-5 2-(3-((4-bromophenyl)amino)-2-oxoquinoxalin-1(2H)-yl)acetic acid 
• 1374748-71-6 2-(3-((4-bromo-2-fluorophenyl)amino)-2-oxoquinoxalin-1(2H)-yl)acetic acid 
• 1374748-72-7 2-(3-((2,4-difluorophenyl)amino)-2-oxoquinoxalin-1(2H)-yl)acetic acid 
• 1374748-73-8 2-(2-oxo-3-((3,4,5-trifluorophenyl)amino)quinoxalin-1(2H)-yl)acetic acid 
• 1374748-74-9 2-(3-(4-fluorophenoxy)-2-oxoquinoxalin-1(2H)-yl)-acetic acid 
• 1374748-75-0 2-(3-(4-bromophenoxy)-2-oxoquinoxalin-1(2H)-yl)-acetic acid 
• 1374748-76-1 2-(3-(4-bromo-2-fluorophenoxy)-2-oxoquinoxalin-1(2H)-yl)acetic acid 
• 1374748-48-7 methyl 2-(3-(4-fluorophenoxy)-2-oxoquinoxalin-1(2H)-yl)acetate 
• 1374748-49-8 methyl 2-(3-(4-bromophenoxy)-2-oxoquinoxalin-1(2H)-yl)acetate 

Relevant academic research and scientific papers

Structure, preparation method and application of quinoxalinone derivative

The invention provides a structure and preparation of a quinoxalinone derivative (a compound as shown in formula I) and application of the pharmaceutically acceptable salt of the quinoxalinone derivative in the preparation of drugs for preventing and/or treating diabetic complication. The quinoxalinone derivative serving as a aldose reductase inhibitor and antioxidant can prevent and/or treat thediabetic complication by inhibiting the activity of aldose reductase and effectively scavenging free radicals and lipid peroxide and inhibiting active oxygen at the same time.

Structure, preparation method and application of a series of quinoxalinone derivatives

The invention provides the structure and synthesis method of a compound shown in the formula I, and application of pharmaceutically acceptable salts of the compound or a mixture of the salts in preparation of drugs for preventing and/or treating diabetic complications. The compound acts as aldose reductase inhibitors and antioxidants and can effectively scavenge free radicals and inhibit the production of lipid peroxides by inhibiting the activity of aldose reductase, and thus the effect of preventing and/or treating the diabetic complications is achieved. The invention further provides a pharmaceutical composition containing the compound and having preventive and/or therapeutic effects on diabetic complications. The formula can be seen in the description.

Exploration of quinoxaline derivatives as antimicrobial and anticancer agents

Novel 2 and 3-substituted quinoxaline derivatives were synthesized through various synthetic pathways, among which cyanoacetamide and cyanoacetohydrazide quinoxaline derivatives 4a-c and 11a-c, respectively, were synthesized. Furthermore, methoxy quinoxaline derivatives 3c and quinoxaline derivatives bearing substituted pyridines 6a,b, 12a,b, and 13a,b were designed to be synthesized. However, we have synthesized acrylohydrazide 5a,b and 7/acrylamide derivatives, Schiff base analogues 14a-f, pyrazole derivatives 15a-e, amide derivatives 16a-f, guanidine derivatives 16 g,h as well as, quinoxalin-2-methylallyl propionate derivative 14g. All the synthesized compounds were confirmed via spectral data and elemental analyses. Moreover, the newly synthesized compounds were evaluated for their antimicrobial activity (Gm +ve, Gm ?ve in comparison to Gentamycin a standard) and fungi (in comparison to Ketoconazole as a standard). Thus, compound 16b showed promising antimicrobial activity against B. subtilis, P. vulgaris, and S. mutants with values ranging from 20 to 27-mm zone of inhibition. While compounds 5a, 14e,f, and 16a,c,d,g,h showed potent antimicrobial activity. Moreover, the National Cancer Institute (NCI) selected 20 compounds that were submitted for anticancer screening against 60 types of cancer cell lines. The most active compounds are 5b and 12a where compound 5b containing 2,4-dichlorophenyl moiety at cyanoacetamide linkage of hydrazine quinoxaline backbone exerted significant growth inhibition activity against Leukemia MOLT-4, Renal cancer UO-31, and Breast cancer MCF-7. In addition, compound 12a having 4,6-diaminopyridinone side chain at position-3 of quinoxaline nucleus exhibited remarkable anticancer activity against renal cancer UO-31.

DNA topoisomerase II inhibition has the activity of modulating kui analogue and its preparation method and application

The invention discloses a quinoxalinone analog with DNA (deoxyribonucleic acid) topoismerase II inhibiting activity, an optical isomer, diastereoisomer or racemic mixture, or pharmaceutically acceptable salt, solvate, prodrug, intermediate or metabolite thereof. The structural general formula is disclosed as Formula (I), wherein R1, R2, R3, R4, R5 and Ar are defined in the specification. The invention also discloses a preparation method of the compounds and application of the compounds as drugs and in treating tumors. The compounds have the advantages of definite curative effect and small toxic and side effects, enriches the varieties of inhibitors of drugs for treating diseases caused by topoismerase II expression abnormity in the prior art, and is hopeful to become clinical drugs with higher therapeutic index.

Design, synthesis and structure-activity relationship of novel quinoxaline derivatives as cancer chemopreventive agent by inhibition of tyrosine kinase receptor

The cancer chemopreventive activity of quinoxaline derivatives 1-20 has been evaluated by studying the inhibitory effect on Epstein-Barr virus early antigen (EBV-EA) activation. The quinoxaline derivatives 1-20 showed inhibitory effect on EBV-EA activation without cytotoxicity on Raji cells. All compounds exhibited dose dependent inhibitory activities, most of them showed significant activity at 1000 mol ratio/12-O-tetradecanoylphorbol-13-acetate (TPA). Compounds 7 and 9 exhibited stronger inhibitory effects on the EBV-EA activation than that of the representative control, oleanolic acid, at the highest measured concentration. In addition, compounds 7-10 showed potent and selective inhibition of human tyrosine kinase (TRK) in liver cancer HepG2 and breast cancer MCF-7 cell lines similar to the positive control, doxorubicin.

METHOD FOR PREPARING SUBSTITUTED N-(3-AMINO-QUINOXALIN-2-YL)-SULFONAMIDES AND THEIR INTERMEDIATES N-(3-CHLORO-QUINOXALIN-2-YL)SULFONAMIDES

The present invention provides a new synthesis for preparing N-(3-amino-quinoxalin-2-yl)-sulfonamides of general formulae (I) or (I') and intermediates sulfonamides of formula (II) or (II'):

An Efficient Synthesis of Quinoxalinone Derivatives as Potent Inhibitors of Aldose Reductase

A novel and facile synthesis of quinoxalinone derivatives was developed in which a wide range of 3-chloroquinoxalin-2(1H)-ones as key intermediates can be generated chemo- and regioselectively in good yields from corresponding quinoxaline-2,3(1H,4H)-diones. This new protocol is arguably superior, as it allows the design and preparation of a variety of bioactive quinoxaline-based compounds, which are particularly effective in the treatment of diabetes and its complications. Through this procedure, a new class of quinoxalinone-based aldose reductase inhibitors were synthesized successfully. Most of the inhibitors, with an N1-acetic acid head group and a substituted C3-phenoxy side chain, proved to be potent and selective. Their IC50 values ranged from 11.4 to 74.8nM. Among them, 2-(3-(4-bromophenoxy)-7-fluoro-2-oxoquinoxalin-1(2H)-yl)acetic acid and 2-(6-bromo-3-(4-bromophenoxy)-2-oxoquinoxalin-1(2H)-yl)acetic acid were the most active. Structure-activity relationship and molecular docking studies highlighted the importance of the ether spacer in the C3-phenoxy side chains, and provided clear guidance on the contribution of substitutions both at the core structure and the side chain to activity.

Synthesis and antimicrobial activity of novel thiazolidinone and azetidinone derivatives

Reaction of 2,3-diketoquinoxaline in presence of phosphorus pentachloride and hydrazine hydrate gives 2-hydrazino-3-hydroxyquinoxalin (4) which on treatment with various aldehydes in appropriate solvent gives 2-p-anisyl-3-(3-hydroxy quinoxalin-2 yl-amino)-4-thiazolidinones (6) and 1-N-(3-hydroxy quinoxalin-2'yl-amino)-4-aryl-3-chloro-2-azetidinones (7). The structure of compounds 6a-6l and 7a-7l has been confirmed by IR and 1H NMR data. All these compounds were tested for their antimicrobial and antifungal activity against different microorganisms.

Part I: Synthesis, cancer chemopreventive activity and molecular docking study of novel quinoxaline derivatives

The reaction of o-phenylene diamine and ethyl oxamate is reinvestigated and led to 3-aminoquinoxalin-2(1H)-one rather than benzimidazole-2-carboxamide as was previously reported. The structure of the obtained quinoxaline has been confirmed by X-ray. The anti-tumor activity of synthesized quinoxalines 1-21 has been evaluated by studying their possible inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13- acetate (TPA). Among the studied compounds 1-21, compounds 12, 8, 13, 18, 17 and 19, respectively, demonstrated strong inhibitory effects on the EBV-EA activation without showing any cytotoxicity and their effects being stronger than that of a representative control, oleanolic acid. Furthermore, compound 12 exhibited a remarkable inhibitory effect on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. The result of the present investigation indicated that compound 12 might be valuable as a potent cancer chemopreventive agent. Moreover, the molecular docking into PTK (PDB: 1t46) has been done for lead optimization of the aforementioned compounds as potential PTK inhibitors.

Synthesis of some 4-substituted hydrazinotetrazolo[1,5-a]quinoxalines

Reaction of 2,3 diketoquinoxaline in presence of phosphorus pentachloride and sodium azide in methanol gives 4-hydroxy tetrazolo[1,5-a]quinoxaline 3 which on reaction with phosphorous oxychloride gives 4-chloro tetrazolo[1,5-a] quinoxaline 4. This on treatment with hydrazine hydrate in ethanol yields 4-hydrazino tetrazolo[1,5-a]quinoxaline 5, which on reaction with various aldehydes in DMF gives 4-substituted hydrazinotetrazolo [1,5-a]quinoxalines 6a-g. The structures of compounds 6a-g have been confirmed by IR and 1H NMR.