171111-70-9Relevant articles and documents
A Difluorobenzoxadiazole Building Block for Efficient Polymer Solar Cells
Zhao, Jingbo,Li, Yunke,Hunt, Adrian,Zhang, Jianquan,Yao, Huatong,Li, Zhengke,Zhang, Jie,Huang, Fei,Ade, Harald,Yan, He
, p. 1868 - 1873 (2016)
A difluorobenzoxadiazole building block is synthesized and utilized to construct a conjugated polymer leading to high-performance thick-film polymer solar cells with a VOC of 0.88 V and a power conversion efficiency of 9.4%. This new building block can be used in many possible polymer structures for various organic electronic applications.
Discovery of novel nitrogenous heterocyclic-containing quinoxaline-1,4-di-N-oxides as potent activator of autophagy in M.tb-infected macrophages
Huang, Lingli,Lu, Qirong,Pan, Yuanhu,Qu, Wei,Xie, Shuyu,Yuan, Zonghui,Zhang, Heying,Zhang, Jie
, (2021)
As a continuation of our research on antimycobacterial agents, a series of novel quinoxaline-1,4-di-N-oxides (QdNOs) containing various nitrogenous heterocyclic moieties at the R6 position were designed and synthesized. Antimycobacterial activities, as well as the cytotoxic effects, of the compounds were assayed. Four compounds (6b, 6f, 6n, and 6o), characterized by 2-carboxylate ethyl or benzyl ester, 6-imidazolyl or 1,2,4-triazolyl, and a 7-fluorine group, exhibited the most potent antimycobacterial activity against M.tb strain H37Rv (MIC ≤ 0.25 μg/mL) with low toxicity in VERO cells (SI = 169.3–412.1). Compound 6o also exhibited excellent antimycobacterial activity in an M.tb-infected macrophage model and was selected for further exploration of the mode of antimycobacterial action of QdNOs. The results showed that compound 6o was capable of disrupting membrane integrity and disturbing energy homeostasis in M.tb. Furthermore, compound 6o noticeably increased cellular ROS levels and, subsequently, induced autophagy in M.tb-infected macrophages, possibly indicating the pathways of QdNOs-mediated inhibition of intracellular M.tb replication. The in vivo pharmacokinetic (PK) profiles indicated that compounds 6o was acceptably safe and possesses favorable PK properties. Altogether, these findings suggest that compound 6o is a promising antimycobacterial candidate for further research.
5(6)-Fluoro-6(5)-R-benzofuroxans: Synthesis and NMR 1H, 13C and 19F studies
Kotovskaya,Romanova,Charushin,Kodess,Chupakhin
, p. 421 - 428 (2004)
5(6)-Fluoro-6(5)-substituted benzofuroxans were obtained by the reactions of 5,6-difluorobenzofuroxan with a number of nucleophiles, such as alkylamines, cycloalkylimines, sodium azide and sodium alkoxides. The features of tautomerism in the series of asymmetrical 5(6)-fluorobenzofuroxans in acetone solutions have been studied by 1H, 13C and 19F NMR.
Quinoxaline-N1,N4-dioxide derivative capable of inhibiting activity of DNA topoisomerase, preparation method and application of quinoxaline-N1,N4-dioxide derivative
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Paragraph 0033-0038; 0050-0054; 0062-0066, (2019/12/25)
The invention belongs to the technical field of biochemistry, and particularly relates to a quinoxaline-N1,N4-dioxide derivative capable of inhibiting the activity of DNA topoisomerase, a preparationmethod and application of the quinoxaline-N1,N4-dioxide derivative. 4,5,-difluoro-2-nitroaniline is used as a raw material for synthesis of the quinoxaline-N1,N4-dioxide derivative, the quinoxaline-N1,N4-dioxide derivative reacts with sodium hypochlorite under catalysis of a basic catalyst, namely sodium hydroxide, and 5,6-difluoro-N-benzofuroxan is obtained; and then the quinoxaline-N1,N4-dioxidederivative reacts with different substrates in Beirut reaction and substitution reaction, and a series of the quinoxaline-N1,N4-dioxide derivative is obtained. According to the quinoxaline-N1,N4-dioxide derivative, the preparation method and application of the quinoxaline-N1,N4-dioxide derivative, quinoxoline-N1,N4-dioxide has good bacteriostatic activity to previously reported gram-negative bacteria, and also had good bacteriostatic activity to actinobacilluspleuropneumoniae and gram-positive bacteria such as staphylococcus aureus and streptococcus pneumoniae.
FLUORINATED BENZOXADIAZOLE-BASED DONOR-ACCEPTOR POLYMERS FOR ELECTRONIC AND PHOTONIC APPLICATIONS
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Paragraph 107; 108; 109, (2017/07/06)
A polymer comprising a repeating unit, which may further comprise one or more repeating units. The present subject matter also relates to a formulation comprising the polymer, and a fullerene, second polymer, or small molecule. The present subject matter further relates to an organic electronic (OE) device comprising a coating or printing ink containing the formulation, where the OE device may be an organic field effect transistor (OFET) device or an organic photovoltaic (OPV) device. The present subject matter also relates to synthesis of monomers, polymers, and the compounds produced therein.
Radical Chemistry and Cytotoxicity of Bioreductive 3-Substituted Quinoxaline Di-N-Oxides
Anderson, Robert F.,Yadav, Pooja,Shinde, Sujata S.,Hong, Cho R.,Pullen, Susan M.,Reynisson, Jóhannes,Wilson, William R.,Hay, Michael P.
, p. 1310 - 1324 (2016/08/25)
The radical chemistry and cytotoxicity of a series of quinoxaline di-N-oxide (QDO) compounds has been investigated to explore the mechanism of action of this class of bioreductive drugs. A series of water-soluble 3-trifluoromethyl (4-10), 3-phenyl (11-19)
Synthesis of novel fluorobenzofuroxans by oxidation of anilines and thermal cyclization of arylazides
Leyva, Socorro,Castanedo, Víctor,Leyva, Elisa
, p. 171 - 175 (2007/10/03)
The synthesis of several fluorobenzofuroxans by oxidation of fluoroanilines and thermal cyclization of fluoroarylazides is presented. The fluorobenzofuroxans prepared in this study presented tautomerism as evidenced by their NMR data. Benzofuroxans in general have biological activity and are synthetic intermediates for the preparation of several compounds with important pharmaceutical applications.
Novel substituted quinoxaline 1,4-dioxides with in vitro antimycobacterial and anticandida activity
Carta, Antonio,Paglietti, Giuseppe,Rahbar Nikookar, Mohammad E,Sanna, Paolo,Sechi, Leonardo,Zanetti, Stefania
, p. 355 - 366 (2007/10/03)
Thirty-six 6(7)-substituted-3-methyl- or 3-halogenomethyl-2-phenylthio-phenylsulphonyl-chloro-quinoxaline 1,4-dioxides belonging to series 3-6 were synthesised and submitted to a preliminary in vitro evaluation for antimycobacterial, anticandida and antibacterial activities. Antitubercular screening showed a generally good activity of 3-methyl-2-phenylthioquinoxaline 1,4-dioxides (3d,e,h-j) against Mycobacterium tuberculosis, and exhibited MIC between 0.39 and 0.78 μg mL-1 (rifampicin MIC=0.25 μg mL-1), whereas in compounds 4d,e, 5a,b,d,e,l and 6b-e,j,l MIC ranged between 1.56 and 6.25 μg mL-1. Results of the antibacterial and anticandida screening showed that 6e and 6l exhibited MIC=0.4 and 1.9 μg mL-1, respectively, against Candida krusei (miconazole MIC=0.9 μg mL-1), and 4i, 5b,d, 6e, MIC=3.9 μg mL-1 against Candida glabrata (miconazole MIC=0.4 μg mL-1), while compounds 3d,l, 5e,l, and 6b,d,e,l showed MIC=15.6 μg mL-1 against Vibrio alginolyticus.
Fluorinated Heterocycles: II. Synthesis of Quinoxaline 1,4-Dioxides
Kotovskaya,Charushin,Chupakhin,Kozhevnikova
, p. 369 - 374 (2007/10/03)
7-Amino-6-fluoroquinoxaline 1,4-dioxides have been synthesized by reaction of 5,6-difluorobenzofuroxan with enamines derived from cycloalkanones and with malononitrile. The transformation of 5,6-difluorobenzofuroxan into quinoxalin 1,4-dioxides in the pre
Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides
Monge, Antonio,Palop, Juan A.,Cerain, Adela Lopez de,Senador, Virginia,Martinez-Crespo, Francisko J.,et al.
, p. 1786 - 1792 (2007/10/02)
Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy.Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy.The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells.Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and /or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells.Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced.Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxide have reduction potentials significantly more positive than Tirapazamine (Epc -0.90 V).The most potent cytotoxins to cells in culture were the 6,7-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine.The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity.Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro.In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine.This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.
