115177-58-7Relevant academic research and scientific papers
From in vitro to in cellulo: Structure-activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa
Storz, Michael P.,Allegretta, Giuseppe,Kirsch, Benjamin,Empting, Martin,Hartmann, Rolf W.
supporting information, p. 6094 - 6104 (2014/08/05)
Recent studies have shown that compounds based on a (2-nitrophenyl)methanol scaffold are promising inhibitors of PqsD, a key enzyme of signal molecule biosynthesis in the cell-to-cell communication of Pseudomonas aeruginosa. The most promising molecule displayed anti-biofilm activity and a tight-binding mode of action. Herein, we report on the convenient synthesis and biochemical evaluation of a comprehensive series of (2-nitrophenyl)methanol derivatives. The in vitro potency of these inhibitors against recombinant PqsD as well as the effect of selected compounds on the production of the signal molecules HHQ and PQS in P. aeruginosa were examined. The gathered data allowed the establishment of a structure-activity relationship, which was used to design fluorescent inhibitors, and finally, led to the discovery of (2-nitrophenyl)methanol derivatives with improved in cellulo efficacy providing new perspectives towards the application of PqsD inhibitors as anti-infectives. This journal is the Partner Organisations 2014.
INTRAMOLECULAR NITRENE INSERTIONS INTO AROMATIC AND HETEROAROMATIC RINGS. PART 8. FLASH VACUUM PYROLYSIS OF 2-AZIDOBENZYLPYRIDINES
Hicks, Martin G.,Jones, Gurnos.,York, David C.
, p. 69 - 76 (2007/10/02)
Flash vacuum pyrolysis of 2-azidobenzylpyridines (9)-(11) at temperatures from 350 to 700 deg C gave mixtures of benzonaphthyridines and their dihydro derivatives as major products.The 3-pyridyl derivative (10) also gave 2-(3-cyanoprop-1-enyl)indole (19).Benzonaphthyridines were also obtained by pyrolysis of 2-aminophenyl(x-pyridyl)methanols (4), (5), and (6), .Treatment of the azides (9)-(11) with aluminium chloride gave the corresponding 2-amino-5-chlorobenzylpyridines (21)-(23).The mechanism of the reaction is discussed.
