550-89-0Relevant articles and documents
Phenazine compound containing oxazole ring and application of phenazine compound as agricultural fungicide (by machine translation)
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, (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)
Synthesis and bioactivities of Phenazine-1-carboxylic acid derivatives based on the modification of PCA carboxyl group
Xiong, Zhipeng,Niu, Junfan,Liu, Hao,Xu, Zhihong,Li, Junkai,Wu, Qinglai
supporting information, p. 2010 - 2013 (2017/04/07)
Phenazine-1-carboxylic acid (PCA) as a natural product widely exists in microbial metabolites of Pseudomonads and Streptomycetes and has been registered for the fungicide against rice sheath blight in China. To find higher fungicidal activities compounds and study the effects on fungicidal activities after changing the carboxyl group of PCA, we synthesized a series of PCA derivatives by modifying the carboxyl group of PCA and their structures were confirmed by 1H NMR and HRMS. Most compounds exhibited significant fungicidal activities in vitro. In particular, compound 6 exhibited inhibition effect against Rhizoctonia solani with EC50 values of 4.35?mg/L and compound 3b exhibited effect against Fusarium graminearum with EC50 values of 8.30?mg/L, compared to the positive control PCA with its EC50 values of 7.88?mg/L (Rhizoctonia solani) and 127.28?mg/L (Fusarium graminearum), respectively. The results indicated that the carboxyl group of PCA could be modified to be amide group, acylhydrazine group, ester group, methyl, hydroxymethyl, chloromethyl and ether group etc. And appropriate modifications on carboxyl group of PCA were useful to extend the fungicidal scope.
PHENAZINE DERIVATIVES AS ANTIMICROBIAL AGENTS
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, (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.
, 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.
Insights on the susceptibility of plant pathogenic fungi to phenazine-1-carboxylic acid and its chemical derivatives
Puopolo, Gerardo,Masi, Marco,Raio, Aida,Andolfi, Anna,Zoina, Astolfo,Cimmino, Alessio,Evidente, Antonio
, p. 956 - 966 (2013/07/26)
Pseudomonas chlororaphis subsp. aureofaciens strain M71 produced two phenazine compounds as main secondary metabolites. These metabolites were identified as phenazine-1-carboxylic acid (PCA) and 2-hydroxyphenazine (2-OH P). In this study, the spectrum of the activity of PCA and 2-OH P was evaluated against a group of crop and forestal plant pathogenic fungi by an agar plate bioassay. PCA was active against most of the tested plant pathogens, while 2-OH P slightly inhibited a few fungal species. Furthermore, four semisynthesised derivatives of PCA (phenazine-1-carboxymethyl, phenazine-1-carboxamide, phenazine-1-hydroxymethyl and phenazine-1-acetoxymethyl) were assayed for their antifungal activity against 11 phytopathogenic species. Results showed that the carboxyl group is a structural feature important for the antifungal activity of PCA. Since the activity of phenazine-1-carboxymethyl and phenazine-1- carboxamide, the two more lipophilic and reversible PCA derivatives remained substantially unaltered compared with PCA.
