33074-70-3Relevant academic research and scientific papers
Silver-Assisted Oxidative Isocyanide Insertion of Ethers: A Direct Approach to β-Carbonyl α-Iminonitriles
Zhao, Leiyang,Liu, Bingxin,Tan, Qitao,Ding, Chang-Hua,Xu, Bin
, p. 9223 - 9227 (2019/11/14)
An efficient silver-assisted oxidative coupling of simple ethers with tert-butyl isocyanide was realized in the presence of DDQ. The direct synthesis of high density functional β-carbonyl α-iminonitriles was achieved in a single step with high yields through the synergetic cascade isocyanide insertion into C(sp3)-H bond, where the isocyanide was used as crucial "CN" and "C=N" sources and the tert-butoxyl group acted as the carbonyl source. Diverse reactivity of β-carbonyl α-iminonitriles has been demonstrated.
Synthesis and biological evaluation of 3-aryl-quinoxaline-2- carbonitrile 1,4-Di-N-oxide derivatives as hypoxic selective anti-tumor agents
Hu, Yunzhen,Xia, Qing,Shangguan, Shihao,Liu, Xiaowen,Hu, Yongzhou,Sheng, Rong
, p. 9683 - 9696 (2012/11/13)
A series of 3-aryl-2-quinoxaline-carbonitrile 1,4-di-N-oxide derivatives were designed, synthesized and evaluated for hypoxic and normoxic cytotoxic activity against human SMMC-7721, K562, KB, A549 and PC-3 cell lines. Many of these new compounds displayed more potent hypoxic cytotoxic activity compared with TX-402 and TPZ in the tumor cells based evaluation, which confirmed our hypothesis that the replacement of the 3-amine with the substituted aryl ring of TX-402 increases the hypoxic anti-tumor activity. The preliminary SAR revealed that 3-chloro was a favorable substituent in the phenyl ring for hypoxic cytotoxicity and 7-methyl or 7-methoxy substituted derivatives exhibited better hypoxic selectivity against most of the tested cell lines. The most potent compound, 7-methyl-3-(3-chlorophenyl)-quinoxaline-2-carbonitrile 1,4-dioxide (9h) was selected for further anti-tumor evaluation and mechanistic study. It also exhibited significant cytotoxic activity against BEL-7402, HepG2, HL-60, NCI-H460, HCT-116 and CHP126 cell lines in hypoxia with IC50 values ranging from 0.31 to 3.16 μM, and preliminary mechanism study revealed that 9h induced apoptosis in a caspase-dependent pathway.
Selective activity against Mycobacterium tuberculosis of new quinoxaline 1,4-di-N-oxides
Vicente, Esther,Pérez-Silanes, Silvia,Lima, Lidia M.,Ancizu, Saioa,Burguete, Asunción,Solano, Beatriz,Villar, Raquel,Aldana, Ignacio,Monge, Antonio
experimental part, p. 385 - 389 (2011/03/17)
New series of 3-phenylquinoxaline 1,4-di-N-oxide with selective activity against Mycobacterium tuberculosis have been prepared and evaluated. Thirty-four of the seventy tested compounds showed an MIC value less than 0.2 μg/mL, a value on the order of the
Synthesis and structure-activity relationship of 3-phenylquinoxaline 1,4-di-N-oxide derivatives as antimalarial agents
Vicente, Esther,Lima, Lidia M.,Bongard, Emily,Charnaud, Sarah,Villar, Raquel,Solano, Beatriz,Burguete, Asuncion,Perez-Silanes, Silvia,Aldana, Ignacio,Vivas, Livia,Monge, Antonio
, p. 1903 - 1910 (2008/12/22)
As a continuation of our research and with the aim of obtaining new antimalarial agents, new series of 3-phenylquinoxaline 1,4-di-N-oxide derivatives have been synthesized following the classical Beirut reaction. Antiplasmodial activity was evaluated in v
Synthesis and antimalarial activity of new 3-arylquinoxaline-2-carbonitrile derivatives
Zarranz, Belen,Jaso, Andres,Aldana, Ignacio,Monge, Antonio,Maurel, Severine,Deharo, Eric,Jullian, Valerie,Sauvain, Michel
, p. 754 - 761 (2007/10/03)
New series of 3-arylquinoxaline-carbonitrile derivatives have been synthesized from various 5-substituted or 5,6-disubstituted benzofuroxanes and tested for their in vitro and in vivo activity against the erythrocytic development of Plasmodium falciparum
