Ueber die Einwirkung von Nitrobenzol auf Anilin bei Gegenwart von Alkali

Wôhl, A.; Aue, Walter A.

doi:10.1002/cber.190103402183

Cited by 66 publications

(20 citation statements)

References 2 publications

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“…The Wohl-Aue reaction 26 , 27 involves the base-promoted condensation between a nitroarene and an aniline to yield a phenazine. With the potential to diversify the HP scaffold at the 6-, 7-, 8- and 9-positions with an array of substituted aniline building blocks, we utilized 2-nitroanisole and 4-methyl-2-nitroanisole in Wohl-Aue condensation reactions with a panel of 14 diverse anilines to produce a total of 20 new HPs in three steps enabling rapid and extensive biological evaluations (Fig.…”

Section: Resultsmentioning

confidence: 99%

A Highly Potent Class of Halogenated Phenazine Antibacterial and Biofilm-Eradicating Agents Accessed Through a Modular Wohl-Aue Synthesis

Yang

Abouelhassan

Burch

et al. 2017

Sci Rep

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Unlike individual, free-floating planktonic bacteria, biofilms are surface-attached communities of slow- or non-replicating bacteria encased within a protective extracellular polymeric matrix enabling persistent bacterial populations to tolerate high concentrations of antimicrobials. Our current antibacterial arsenal is composed of growth-inhibiting agents that target rapidly-dividing planktonic bacteria but not metabolically dormant biofilm cells. We report the first modular synthesis of a library of 20 halogenated phenazines (HP), utilizing the Wohl-Aue reaction, that targets both planktonic and biofilm cells. New HPs, including 6-substituted analogues, demonstrate potent antibacterial activities against MRSA, MRSE and VRE (MIC = 0.003–0.78 µM). HPs bind metal(II) cations and demonstrate interesting activity profiles when co-treated in a panel of metal(II) cations in MIC assays. HP 1 inhibited RNA and protein biosynthesis while not inhibiting DNA biosynthesis using 3H-radiolabeled precursors in macromolecular synthesis inhibition assays against MRSA. New HPs reported here demonstrate potent eradication activities (MBEC = 0.59–9.38 µM) against MRSA, MRSE and VRE biofilms while showing minimal red blood cell lysis or cytotoxicity against HeLa cells. PEG-carbonate HPs 24 and 25 were found to have potent antibacterial activities with significantly improved water solubility. HP small molecules could have a dramatic impact on persistent, biofilm-associated bacterial infection treatments.

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Section: Resultsmentioning

confidence: 99%

A Highly Potent Class of Halogenated Phenazine Antibacterial and Biofilm-Eradicating Agents Accessed Through a Modular Wohl-Aue Synthesis

Yang

Abouelhassan

Burch

et al. 2017

Sci Rep

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“…A majority of the methods to synthesize phenazines involve generating the fused tricyclic skeleton through the construction of the central heterocyclic ring. An early approach, which employs a Wohl–Aue procedure, involves heating aniline and nitrobenzene above 200 °C to yield phenazines in moderate yields along with the formation of a significant amount of byproduct 4. Methods to prepare phenazine‐ N ‐oxide and phenazine‐ N , N′ ‐dioxide are also known, and upon deoxygenation these compounds afford phenazines in moderate yields 5.…”

Section: Introductionmentioning

confidence: 99%

Straightforward Access to Water‐Soluble Unsymmetrical Sulfoxanthene Dyes: Application to the Preparation of Far‐Red Fluorescent Dyes with Large Stokes’ Shifts

Chevalier

Renard

Romieu

2014

Chemistry A European J

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An efficient synthesis of water-soluble unsymmetrical sulforhodamine/sulforhodol fluorophores containing a single julolidine fragment is presented. Owing to their valuable spectral properties in aqueous buffers, these dyes, especially those bearing a free aniline or phenol moiety, are valuable components of fluorogenic probes for a variety of biosensing applications. A further extension of this synthetic methodology to unusual phenols, namely 7-N,N-dialkylamino-4-hydroxy coumarins has enabled us to provide a new family water-soluble dyes of large Stokes' shift with far-red spectral features.

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“…This condensation is an intramolecular variant of the Wohl-Aue reaction in which an aromatic nitro compound is condensed with an aniline in the presence of base to furnish a phenazine [1]. Investigations of the mechanism of the Wohl-Aue reaction have shown that the N-oxide, which is present in compound 1 , is an intermediate in the formation of phenazines which may become the main product depending on the reaction conditions [2].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Crystal Structure of a Phenazine N-oxide

2013

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The preparation and crystal structure of 8-chloro-1H-pyrrolo[2,3-b]phenazine 5-oxide (1) are described. Compound 1 formed dark purple crystals from deeply colored solution in methanol. Crystal plates were in the triclinic system, P-1 space group with unit cell parameters a = 6.9514(8), b = 9.1568(10), c = 10.2067(11), α = 84.509(2), β = 82.936(2), γ = 72.357(2) and a cell volume of 613.25(12) A−3. The title compound which contains the first example of the extensively conjugated pyrrolo-phenazine N-oxide system exhibits strong light absorption in the green to cyan wavelength range which disappears upon protonation.

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Ueber die Einwirkung von Nitrobenzol auf Anilin bei Gegenwart von Alkali

Cited by 66 publications

References 2 publications

A Highly Potent Class of Halogenated Phenazine Antibacterial and Biofilm-Eradicating Agents Accessed Through a Modular Wohl-Aue Synthesis

A Highly Potent Class of Halogenated Phenazine Antibacterial and Biofilm-Eradicating Agents Accessed Through a Modular Wohl-Aue Synthesis

Straightforward Access to Water‐Soluble Unsymmetrical Sulfoxanthene Dyes: Application to the Preparation of Far‐Red Fluorescent Dyes with Large Stokes’ Shifts

Synthesis and Crystal Structure of a Phenazine N-oxide

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