Azo Dyes

Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, R.; Kunde, Klaus; Engel, Aloys

doi:10.1002/14356007.a03_245

Cited by 39 publications

(30 citation statements)

References 75 publications

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“…The core of the diazobenzene compounds was constructed by azo coupling 30 of the diazonium chloride intermediate 2 with appropriately functionalized phenol (Scheme 1). 31 For C ring diazo analogs, 4-aminobenzenesulfonyl chloride precursors were first coupled to functionalized aromatic amines.…”

Section: Methodsmentioning

confidence: 99%

Structure-Guided Design of Potent Diazobenzene Inhibitors for the BET Bromodomains

et al. 2013

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BRD4, characterized by two acetyl-lysine binding bromodomains and an extra-terminal (ET) domain, is a key chromatin organizer that directs gene activation in chromatin through transcription factor recruitment, enhancer assembly, and pause release of the RNA polymerase II complex for transcription elongation. BRD4 has been recently validated as a new epigenetic drug target for cancer and inflammation. Our current knowledge of the functional differences of the two bromodomains of BRD4, however, is limited, hindered by the lack of selective inhibitors. Here, we report our structure-guided development of diazobenzene-based small molecule inhibitors for the BRD4 bromodomains that have over 90% sequence identity at the acetyl-lysine binding site. Our lead compound MS436, through a set of water-mediated interactions, exhibits low nanomolar affinity (estimated Ki of 30–50 nM) with preference for the first bromodomain over the second. We demonstrated that MS436 effectively inhibits BRD4 activity in NF-κB-directed production of nitric oxide and pro-inflammatory cytokine interleukin-6 in murine macrophages. MS436 represents a new class of bromodomain inhibitors and will facilitate further investigation of the biological functions of the two bromodomains of BRD4 in gene expression.

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Section: Methodsmentioning

confidence: 99%

Structure-Guided Design of Potent Diazobenzene Inhibitors for the BET Bromodomains

et al. 2013

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“…For applications of diazonium compounds, see: Patai (1978); Hunger et al (2005). For the synthesis and crystal structures of Hg(II) and Cd(II) complexes with [1,3-bis(2-methoxyphenyl)]triazene, see: Rofouei, Hematyar et al (2009); Rofouei, Melardi et al (2009).…”

Section: Related Literaturementioning

confidence: 99%

4-[(4-Chlorophenyl)diazenyl]-3-methoxyaniline

Rofouei¹,

Ghalami²,

Gharamaleki³

et al. 2011

Acta Cryst E

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The title compound, C13H12ClN3O, exhibits a trans geometry about the N=N double bond in the solid state. The dihedral angle between the rings is 22.20 (8)°. Intermolecular N—H⋯O hydrogen bonds between the amine and methoxy groups lead to the formation of a chain-like polymer along the c axis with a C(6) graph set. There is also weak non-classical C—H⋯N hydrogen bonds involving an aromatic C—H group and a diazenyl N atom, which connect the chains into a two-dimensional framework.

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“…Brominated anilines are used as coupling components in azo dye production [29]. In contrast to the halogenated naphthalenes this compound was not only detected in all hydrolysis extracts but also in extracts obtained after BBr 3 -treatment and, exclusively, after RuO 4 -oxidation.…”

Section: Resultsmentioning

confidence: 87%

Quantitation of Nonextractable Anthropogenic Quantitation of Nonextractable Anthropogenic Sediments after Chemical Degradation

Schwarzbauer

Ricking

Littke

2003

Acta hydrochim. hydrobiol.

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Four highly contaminated sediment samples obtained from three sampling locations of the Teltow Canal, Berlin, were investigated by quantitation of extractable and nonextractable organic contaminants. The selection of the anthropogenic contaminants (including chlorinated and brominated naphthalenes, 2, 4, 6‐tribromoaniline, phthalates, tri‐n‐butylphosphate, 2, 2, 4‐trimethyl‐1, 3‐pentanediol diisobutyrate, bisphenol A, butylated nitrophenols, 4‐nitrobenzoic acid, galaxolide, and tonalide) based on the results of extended GC‐MS screening analyses applied to the extracts of the sediment samples as well as to the extracts derived from selective chemical degradation procedures. In detail, alkaline hydrolyses, BBr3‐treatment and RuO4‐oxidation were applied to the pre‐extracted sediment samples in both a separate and a sequential mode.

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Azo Dyes

Cited by 39 publications

References 75 publications

Structure-Guided Design of Potent Diazobenzene Inhibitors for the BET Bromodomains

Structure-Guided Design of Potent Diazobenzene Inhibitors for the BET Bromodomains

4-[(4-Chlorophenyl)diazenyl]-3-methoxyaniline

Quantitation of Nonextractable Anthropogenic Quantitation of Nonextractable Anthropogenic Sediments after Chemical Degradation

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