19803-53-3Relevant academic research and scientific papers
Energetic and structural characterization of 2-R-3-methylquinoxaline-1,4- dioxides (R = benzoyl or tert-butoxycarbonyl): Experimental and computational studies
Gomes, Jose R. B.,Sousa, Emanuel A.,Goncalves, Jorge M.,Gales, Luis,Damas, Ana M.,Gomes, Paula,Pandey, Siddharth,Acree Jr., William E.,Da Silva, Maria D. M. C. Ribeiro
, p. 491 - 498 (2007)
The gaseous standard molar enthalpies of formation of two 2-R-3-methylquinoxaline-1,4-dioxides (R = benzoyl or tert-butoxycarbonyl), at T = 298.15 K, were derived using the values for the enthalpies of formation of the compounds in the condensed phase, me
Diacylfuroxans Are Masked Nitrile Oxides That Inhibit GPX4 Covalently
Eaton, John K.,Kramm, Anneke,Ruberto, Richard A.,Schreiber, Stuart L.,Viswanathan, Vasanthi S.
supporting information, (2020/01/02)
GPX4 represents a promising yet difficult-to-drug therapeutic target for the treatment of, among others, drug-resistant cancers. Although most GPX4 inhibitors rely on a chloroacetamide moiety to modify covalently the protein's catalytic selenocysteine residue, the discovery and mechanistic elucidation of structurally diverse GPX4-inhibiting molecules have uncovered novel electrophilic warheads that bind and inhibit GPX4. Here, we report our discovery that diacylfuroxans can act as masked nitrile oxide prodrugs that inhibit GPX4 covalently with unique cellular and biochemical reactivity compared to existing classes of GPX4 inhibitors. These observations illuminate a novel molecular mechanism of action for biologically active furoxans and also expand the collection of reactive groups capable of targeting GPX4.
Silica gel catalyzed synthesis of quinoxialine 1,4-dioxides under solvent-free conditions using microwave irradiation
Sumiyoshi, Yusuke,Saito, Hiroaki,Miyairi, Shinichi,Takabatake, Tohru
scheme or table, p. 905 - 909 (2009/09/29)
We report on the simple and quick synthesis of quinoxaline 1,4-dioxides in solvent-free conditions under microwave irradiation. Heating of various benzofuroxans and β-ketoesters or 1,3-diketones adsorbed on silica gel in a microwave oven for two minutes affords diverse biologically attractive quinoxaline 1,4-dioxides in high to excellent yields. Silica gel functions not only as support using microwave but also as catalyst and dehydration reagent.
Synthesis of quinoxaline 1,4-dioxides from benzofuroxan proceeds not in, but on zeolite
Takabatake, Tohru,Ito, Hiroyasu,Takei, Aki,Miyazawa, Tomoyuki,Hasegawa, Minoru,Miyairi, Shinichi
, p. 537 - 550 (2007/10/03)
Quinoxaline synthesis using Na-zeolite A as a catalyst to proceeds in a better yield than that using zeolite X. The pore diameter of zeolite X is large enough to allow the benzofuroxan derivatives access to cages, therefore part of benzofuroxan is adsorbe
Synthesis of new 2-acetyl and 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents
Jaso, Andres,Zarranz, Belen,Aldana, Ignacio,Monge, Antonio
, p. 791 - 800 (2007/10/03)
A series of 2-acetyl and 2-benzoyl-6(7)-substituted quinoxaline 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. The results show that 2-acetyl-3-methylquinoxaline 1,4-di-N-oxide derivatives with chlorine,
The reactions of benzofuroxan with carbonyl compounds on the surface of solid catalysts
Takabatake,Hasegawa,Hasegawa
, p. 1477 - 1480 (2007/10/02)
The cyclocondensations of benzofuroxan 1a with carbonyl compounds were smoothly and efficiently carried out by the adsorption of the components on the surface of silica gel or a molecular sieve to form a 2,3-disubstituted quinoxaline 1,4-dioxide. When the
A New Synthesis of 2,3-Disubstituted Quinoxaline 1,4-Dioxide Catalyzed by Molecular Sieves
Takabatake, Tohru,Hasegawa, Minoru
, p. 529 - 530 (2007/10/02)
The syntheses of 2,3-disubstituted quinoxaline 1,4-dioxides are smoothly and efficiently carried out by the adsorption of the components on molecular sieve 3A (powder) from benzofuroxan 1 and 1,3-diketones, 3-oxoalkanoic esters, or 3-oxoalkanamides 2.
Reactions of Benzofuroxan with 1,3-Diketones or β-Ketoesters on Silica Gel or Alumina
Hasegawa, Minoru,Takabatake, Tohru
, p. 938 (2007/10/02)
The cyclocondensation of benzofuroxan with 1,3-diketones, 3-oxoalkanoic esters, butanedioic esters, or 3-oxoalkanamides in the presence of silica gel (adsorption of the components on silica gel) represents a convenient method for the synthesis of 2,3-disu
