54420-95-0Relevant academic research and scientific papers
Design, synthesis and biological evaluations of diverse Michael acceptor-based phenazine hybrid molecules as TrxR1 inhibitors
Zhong, Yucheng,Liu, Jing,Cheng, Xiangyu,Zhang, Hao,Zhang, Chunhua,Xia, Zhuolu,Wu, Zhongxi,Zhang, Lu,Zheng, Yuting,Gao, Zhanyu,Jiang, Zhidong,Wang, Zhixiang,Huang, Dechun,Lu, Yuanyuan,Jiang, Feng
, (2021/03/01)
A series of novel phenazine derivatives (1~27) containing the Michael acceptor scaffolds were designed and synthesized in this study. Some compounds exhibited selective cytotoxicity against Bel-7402 cancer cell line in vitro, in which compound 26 were found to have the best antiproliferative activity. Meanwhile, compound 26 showed no obvious cell toxicity against human normal liver epithelial L02 cells, which means this compound possessed a better safety potential. In the following research, compound 26 was verified to inhibit TrxR1 enzyme activity, ultimately resulting in cellular molecular mechanism events of apoptosis including growth of intracellular ROS level, depletion of reduced Trx1, liberation of ASK1 and up-regulation of p38, respectively. Together, all these evidences implicated that compound 26 acted as the TrxR1 inhibitor against Bel-7402 cells, and could activate apoptosis through the ROS-Trx-ASK1-p38 pathway.
Synthesis, crystal structure and bioactivity of phenazine-1-carboxylic acylhydrazone derivatives
Huang, Yali,Liang, Xi,Liu, Hua,Luo, Fang,Redshaw, Carl,Shen, Lingyi,Wu, Ning,Wu, Shouting,Xu, Hong,Yang, Xianjiong,Zhang, Qilong
, (2021/09/08)
A phenazine-1-carboxylic acid intermediate was synthesized from the reaction of aniline and 2-bromo-3-nitro-benzoic acid. It was then esterified and reacted with hydrazine hydrate to af-ford phenazine-1-carboxylic hydrazine. Finally, 10 new hydrazone compounds 3a–3j were obtained by the condensation reaction of phenazine-1-carboxylic acid hydrazide and the respective aldehyde-containing compound. The structures were characterized by1H and13C NMR spectros-copy, MS and single crystal X-ray diffraction. The antitumor activity of the target compounds in vitro (HeLa and A549) was determined by thiazolyl blue tetrazolium bromide. The results showed that compound (E)-N′-(2-hydroxy-4-(2-(piperidine-1-yl) ethoxy) benzyl) phenazine-1-carbonyl hydrazide 3d exhibited good cytotoxic activity.
Phenazine derivative serving as TrxR1 inhibitor, intermediate product, preparation methods of phenazine derivative and intermediate product and application of phenazine derivative
-
Paragraph 0023; 0033-0034, (2019/09/14)
The invention discloses a phenazine derivative which has a structure shown in a general formula I and serves as a TrxR1 inhibitor, an intermediate product, and a preparation method and application ofthe phenazine derivative. In the formula I, R is H or CH3; R is selected from H, CH2N(CH3)2, phenyl, (4-fluoro)-phenyl, (3-trifluoromethyl)-phenyl, (4-chloro)-phenyl and (2,5-dichloro)-phenyl; and R is H. The phenazine derivative disclosed by the invention has significant inhibitory activity on TrxR1, especially has significant anti-proliferative activity on HepG2 cell strains, and can beused for preparing anti-tumor drugs.
Phenazine compound containing oxazole ring and application of phenazine compound as agricultural fungicide (by machine translation)
-
Paragraph 0020; 0022, (2019/12/25)
The present invention relates to an oxazole ring-containing phenazine compound, the use of, and such a compound as an. agricultural fungicide, wherein the compound has: the following general formula (I). A compound represented R by the, formula, #, #, STR7, #, #, wherein, R represents a, 1 - 6 hydrogen, and atom, 2-4 a R halogeno-methyl group, an amino group, a phenyl group, a methoxy group, and a phenyl group. (by machine translation)
Phenazine carboxylate compound and use thereof
-
Paragraph 0058; 0059; 0060; 0061, (2016/10/08)
The invention discloses a phenazine carboxylate compound which is represented by a formula I shown in the description, wherein R is selected from C4-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, aryl C1-C3 alkyl or C3-C8 cycloalkyl; the aryl is selected from a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a furan ring, a thiophene ring, a pyrazol ring, an imidazole ring and a triazole ring which are substituted by 1-5 same or different R1; R1 is selected from hydrogen, halogen, hydroxyl, amino, nitryl, cyano, C1-C6 alkyl, C1-C6 halogenated alkyl, C1-C6 alkyl amino, C1-C6 halogenated alkyl amino, C1-C6 alkoxyl or C1-C6 halogenated alkoxyl. The compound represented by the formula I has excellent sterilizing bacterial and can be used for preventing plant fungi diseases.
PHENAZINE DERIVATIVES AS ANTIMICROBIAL AGENTS
-
Paragraph 00306-00309, (2015/07/15)
The present invention provides novel phenazine derivatives, such as compounds of Formula (I) and (II), and pharmaceutically acceptable salts thereof. The compounds of the invention are expected to be anitmicrobial agents and may act by a microbial warfare strategy (e.g., a reactive oxygen species (ROS)-based competition strategy). The present invention also provides pharmaceutical compositions, kits, uses, and methods that involve the compounds of the invention and may be useful in preventing or treating a microbial infection (e.g., a bacterial infection) in a subject, inhibiting the growth and/or reproduction of a microorganism (e.g., a bacterium), killing a microorganism (e.g., a bacterium), inhibiting the formation and/or growth of a biofilm, or reducing or clearing a biofilm.
Phenazine antibiotic inspired discovery of potent bromophenazine antibacterial agents against Staphylococcus aureus and Staphylococcus epidermidis
Borrero, Nicholas V.,Bai, Fang,Perez, Cristian,Duong, Benjamin Q.,Rocca, James R.,Jin, Shouguang,Huigens Iii, Robert W.
supporting information, p. 881 - 886 (2014/02/14)
Nearly all clinically used antibiotics have been (1) discovered from microorganisms (2) using phenotype screens to identify inhibitors of bacterial growth. The effectiveness of these antibiotics is attributed to their endogenous roles as bacterial warfare agents against competing microorganisms. Unfortunately, every class of clinically used antibiotic has been met with drug resistant bacteria. In fact, the emergence of resistant bacterial infections coupled to the dismal pipeline of new antibacterial agents has resulted in a global health care crisis. There is an urgent need for innovative antibacterial strategies and treatment options to effectively combat drug resistant bacterial pathogens. Here, we describe the implementation of a Pseudomonas competition strategy, using redox-active phenazines, to identify novel antibacterial leads against Staphylococcus aureus and Staphylococcus epidermidis. In this report, we describe the chemical synthesis and evaluation of a diverse 27-membered phenazine library. Using this microbial warfare inspired approach, we have identified several bromophenazines with potent antibacterial activities against S. aureus and S. epidermidis. The most potent bromophenazine analogue from this focused library demonstrated a minimum inhibitory concentration (MIC) of 0.78-1.56 μM, or 0.31-0.62 μg mL-1, against S. aureus and S. epidermidis and proved to be 32- to 64-fold more potent than the phenazine antibiotic pyocyanin in head-to-head MIC experiments. In addition to the discovery of potent antibacterial agents against S. aureus and S. epidermidis, we also report a detailed structure-activity relationship for this class of bromophenazine small molecules.
UNEQUIVOCAL SYNTHESIS OF PHENAZINE-1-CARBOXYLIC ACIDS: SELECTIVE DISPLACEMENT OF FLUORINE DURING ALKALINE BOROHYDRIDE REDUCTION OF N-(2-FLUOROPHENYL)-3-NITROANTHRANILIC ACIDS
Rewcastle, Gordon W,Denny, William A
, p. 1171 - 1180 (2007/10/02)
Reductive cyclization of substituted N-(2-fluorophenyl)-3-nitroanthranilic acids provides an unequivocal synthetic route to 6-, 8- and 9-substituted phenazine-1-carboxylic acids.
