3882-44-8Relevant 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.
An investigation on the second-order NLO properties of novel cationic cyclometallated Ir(III) complexes of the type [Ir(2-phenylpyridine) 2(9-R-4,5-diazafluorene)]+ (R = H, fulleridene) and the related neutral complex with the new 9-fulleriden-4-monoazafluorene ligand
Dragonetti, Claudia,Valore, Adriana,Colombo, Alessia,Righetto, Stefania,Rampinini, Giovanni,Colombo, Francesca,Rocchigiani, Luca,MacChioni, Alceo
experimental part, p. 72 - 78 (2012/04/04)
Novel cationic cyclometallated Ir(III) complexes bearing diaza- or monoazafluorene substituted or not with a C60-fullerene moiety have been synthesized together with a novel interesting ligand 9-fulleriden-4- monoazafluorene and the related Ir(III) neutral complex [Ir(ppy) 2(9-fulleriden-4-monoazafluorene)]. All complexes show a negative large value of μβ1.907 (-600 to -2190 × 10 -48 esu), as determined by the Electric Field Induced Second Harmonic generation (EFISH) technique working at 1.907 μm in 10-3 M CH2Cl2 solution. The NLO response increases upon introduction of the fullerene moiety, due to a decrease of the interaction forces between the anion and cation within the ion pair which leads to an increase of the percentage of free ions, as evidenced by diffusion NMR experiments. Besides, it appeared that for the neutral complex [Ir(ppy) 2(9-fulleriden-4-monoazafluorene)] the EFISH μβ 1.907 value is lower than that of cationic Ir(III) complexes, but comparable or slightly lower to the values of other neutral Ir(III) complexes such as [Ir(ppy)2(RCOCR′COR)] (ppy = cyclometallated 2-phenylpyridine; R = Me, Ph; R′ = H, 2,4-dinitrophenyl), confirming that the second-order NLO response of these neutral chromophores is dominated by ILCT processes concerning cyclometallated 2-phenylpyridines.
Cyclising Nucleophilic Addition to Azinium Systems. Part 2. Reactions of 3-Acylpyridinium Hydrazones.
Street, Jonathan D.,Baradarani, M. Mehdi,Beddoes, Roy L.,Mills, Owen S.,Joule, John A.
, p. 1247 - 1285 (2007/10/02)
3-Acyl-1-methylpyridinium tosyl- and benzoylhydrazines lose a side-chain N-hydrogen on treatment with mild base thus forming zwitterions, isolable in some cases; intramolecular nucleophilic cyclising addition to the pyridinium nucleus in these was observe
Intramolecular Nitrene Insertions into Aromatic and Heteroaromatic Systems. Part 7. Insertions into Electron-deficient Rings
Carde, Robert N.,Hayes, Peter C.,Jones, Gurnos,Cliff, Cynthya J.
, p. 1132 - 1142 (2007/10/02)
A number of routes to o-aminotriphenylmethanes are described, where one benzene ring, or both, carry potential ester groups.The most useful synthon is shown to be the 1,3-dioxan-2-yl substituent, and using this methyl 2-aminodiphenylmethane-4'-carboxylate (18) and dimethyl 2-aminotriphenylmethane-4',4''-dicarboxylate (28) have been prepared.The azides from these, respectively (19) and (29), on thermolysis at 200 deg C gave azepinoindoles (48) and (51), the first examples of ring expansion by an arylnitrene of benzene rings with electron-withdrawing substituents.Also reported are syntheses of 3- and 4-(2-azidobenzyl)pyridines (38) and (39), and of 2-(2-azidobenzyl)thiazole (40); decomposition of these azides gave mainly polymers.
